Stability Constants of Complexes of Zn2+, Cd2+, and Hg2+ with Organic Ligands: QSPR Consensus

Stability Constants of Complexes of Zn2+, Cd2+, and Hg2+ with Organic Ligands: QSPR Consensus Modeling and Design of New Metal Binders

Vitaly Solov’ev 1, Igor Sukhno 2, Vladimir Buzko 2, Aleksey Polushin 2, Gilles Marcou 3, Aslan Tsivadze 1, Alexandre Varnek 3

1Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy prospect, 31a, 119991, Moscow, Russia

2Kuban StateUniversity, 149 Stavropolskaya st., Krasnodar, Russia

3Laboratoire d’Infochimie, UMR 7177 CNRS, Université de Strasbourg, 4, rue B.Pascal, Strasbourg, 67000, France

Supporting Information

Table SM1. QSPR modeling of stability constants: The names of organic ligands (L) and experimental stability constant values (logK) for the equilibrium Zn2+ + L = (Zn2+)L in water at 298 K and an ionic strength 0.1 M.

no. / ligand / logK
1 / Methanoic acid; H.COOH / 0.95
2 / Methylphosphonic acid; CH3.PO3H2 / 2.6
3 / Methylphosphoric acid; CH3OP(O)(OH)2 / 2.22
4 / Aminomethylphosphonic acid; H2N.CH2.PO3H2 / 5
5 / Ethanedioic acid; (COOH)2 / 3.5
6 / Ethanoic acid; CH3.COOH / 0.93
7 / Imino-N,N-bis(methylenephosphonic acid); HN(CH2PO3H2)2 / 9.03
8 / 1,3-Diazole, imidazole; C3H4N2 / 2.56
9 / 2-Aminoethanoic acid; H2N.CH2.COOH / 4.93
10 / Acetohydroxamic acid, N-Hydroxyacetamide; CH3.CO.NHOH / 5.22
11 / 2-Aminoethanoic acid amide; H2N.CH2.CO.NH2 / 3.28
12 / 2-Amino-N-hydroxyacetamide, Glycine hydroxamic acid; H2N.CH2.CO.NH.OH / 5.38
13 / 2-Aminoethanol; H2N.CH2.CH2.OH / 2.41
14 / Ethylphosphonic acid; CH3.CH2.PO3H2 / 2.67
15 / 1-Aminoethanephosphonic acid; CH3.CH(NH2).PO3H2 / 5.82
16 / 1,2-Diaminoethane; H2N.CH2.CH2.NH2 / 5.91
17 / Propanedioic acid; CH2(COOH)2 / 2.97
18 / 1,3-Diaminopropane; H2N.CH2.CH2.CH2.NH2 / 6
19 / (Dimethylamino)-N-methylenediphosphonic acid; (CH3)2N.CH(PO3H2)2 / 9.27
20 / N-Methylimino-N,N-bis(methylenephosphonic acid); CH3.N(CH2PO3H2)2 / 10.44
21 / Nitrilotris(methylenephosphonic acid); N(CH2PO3H2)3 / 16.3
22 / 2-Aminopropanoic acid; H2N.CH(CH3).COOH / 4.63
23 / 3-Aminopropanoic acid; H2N.CH2.CH2.COOH / 4.15
24 / N-Methyl-2-aminoethanoic acid; CH3.NH.CH2.COOH / 4.53
25 / N-Methylacetohydroxamic acid; CH3.CO.N(OH)CH3 / 4.59
26 / Propanohydroxamic acid; C2H5CONHOH / 5.15
27 / 2-Amino-3-mercaptopropanoic acid; H2N.CH(CH2.SH)COOH / 8.97
28 / 2-Amino-3-hydroxypropanoic acid; H2N.CH(CH2.OH)COOH / 5.1
29 / N-(Phosphonomethyl)glycine; H2O3P.CH2.NH.CH2.COOH / 8.74
30 / Serine dihydrogenphosphate, O-Phosphoserine; NH2.CH(CH2.OPO3H2).COOH / 5.88
31 / 2,3-Diaminopropanoic acid; H2N.CH2.CH(NH2).COOH / 6.39
32 / 2-Amino-N-hydroxypropanamide, Alanine hydroxamic acid; CH3.CH(NH2).CO.NH.OH / 5.37
33 / 2-(Methylamino)ethanol; HO.CH2.CH2.NH.CH3 / 5.3
34 / Glycylaminomethylphosphonic acid; / 4.17
35 / 1,3-Dihydroxypropyl-2-phosphoric acid; HOCH2CH(OPO3H2)CH2OH / 2.23
36 / 2,3-Dihydroxypropylphosphoric acid, Glycerol 1-phosphate; HO.CH2.CH(OH).CH2.OPO3H2 / 2.13
37 / 1,1-Dimethyl-1-aminomethylphosphonic acid; H2N.C(CH3)2.PO3H2 / 6.13
38 / Dimethylaminomethylphosphonic acid; (CH3)2N.CH2.PO3H2 / 5.45
39 / 2-Oxosuccinic acid, Oxalacetic acid; HOOC.CH2.CO.COOH / 2.41
40 / 4-Methyl-1,3-diazole; C3H3N2.CH3 / 2.44
41 / 2-Ketobutanoic acid; CH3.CH2.CO.COOH / 1.69
42 / 3-Ketobutanoic acid; CH3.CO.CH2.COOH / 0.83
43 / 1,4-Butanedioic acid; HOOC.CH2.CH2.COOH / 2
44 / Methylpropanedioic acid; HOOC.CH(CH3).COOH / 2.64
45 / 2,2'-Thiodiglycolic acid, Thiodiethanoic acid; HOOC.CH2.S.CH2.COOH / 3.2
46 / 2-Mercaptosuccinic acid, 2-Sulfanyl-1,4-butanedioic acid; HOOC.CH(SH).CH2.COOH / 8.24
47 / 2-Hydroxybutane-1,4-dioic acid, Hydroxy-succinic acid; HOOC.CH2.CH(OH).COOH / 2.96
48 / Di(carboxy)methyl ether, 2,2'-Oxydiethanoic acid; HOOC.CH2.O.CH2.COOH / 3.65
49 / (S)-Azetidine-2-carboxylic acid; / 5.5
50 / Thiazolidine-4-carboxylic acid; C3H6NS.COOH / 3.15
51 / Aminobutanedioic acid; H2N.CH(CH2.COOH).COOH / 5.69
52 / Ethylenebis(iminomethylenephosphonous acid) / 6.16
53 / 1,2-Diaminoethane-N,N'-bis(methylenephosphonic) acid; (H2O3P.CH2.NH.CH2)2 / 9.12
54 / 1,1,1,5,5,5-Hexafluoropentane-2,4-dione; F3C.CO.CH2.CO.CF3 / 1.6
55 / Iminodiethanoic acid; HN(CH2.COOH)2 / 7.24
56 / 2-Aminobutanedioic acid 4-amide; H2N.CH(CH2.CO.NH2).COOH / 4.4
57 / Glycyl-glycine; H2N.CH2.CO.NH.CH2.COOH / 3.62
58 / 2-Methylpropanoic acid; CH3.CH(CH3).COOH / 1.01
59 / n-Butanoic acid; CH3.CH2.CH2.COOH / 1.08
60 / 3-Hydroxybutanoic acid; CH3.CH(OH).CH2.COOH / 1.14
61 / 2-Aminobutanoic acid; CH3.CH2.CH(NH2).COOH / 4.41
62 / 2-Amino-3-methylmercaptopropanoic acid; H2N.CH(CH2.S.CH3)COOH / 4.3
63 / 2-Amino-3-hydroxybutanoic acid; H2N.CH(CH(OH).CH3)COOH / 4.66
64 / 2-Amino-4-hydroxybutanoic acid; HO.CH2.CH2.CH(NH2).COOH / 4.54
65 / O-Phospho-2-methylserine; / 6.09
66 / O-Phospho-threonine; / 6.16
67 / 2,4-Diaminobutanoic acid; H2N.CH2.CH2.CH(NH2)COOH / 6.78
68 / 2-Amino-3-(methylamino)propanoic acid, CH3.NH.CH2.CH(NH2)COOH / 5.98
69 / Diaminoethane-N-ethanoic acid; H2N.CH2.CH2.NH.CH2.COOH / 8.28
70 / 2-(Ethylamino)ethanol; CH3.CH2.NH.CH2.CH2.OH / 5.34
71 / 2-Amino-2-(hydroxymethyl)-propan-1,3-diol; (HO.CH2)3C.NH2 / 1.94
72 / N-Carboxymethyl-N,N-bis(methylenephosphonic acid); HOOC.CH2.N(CH2.PO3H2)2 / 14.46
73 / Alanylaminomethylphosphonic acid; / 3.82
74 / 2,4-Diamino-N-hydroxybutanamide; / 7.21
75 / n-Butyl phosphoric acid; C4H9.O.PO(OH)2 / 2.3
76 / DL-2,3-Diaminobutane; H2N.CH(CH3).CH(CH3).NH2 / 5.94
77 / N,N'-Dimethyl-1,2-diaminoethane; CH3.NH.CH2.CH2.NH.CH3 / 4.47
78 / N-(2-Hydroxyethyl)diaminoethane, 1,4-Diaza-7-oxaheptane; H2N.CH2.CH2.NH.CH2.CH2.OH / 5.28
79 / N-Butyldiphosphoric acid; / 4.4
80 / N-Ethyliminobis(methylenephosphonic) acid; C2H5N(CH2PO3H2)2 / 9.65
81 / 1,4,7-Triazaheptane, 2,2'Iminobis(ethylamine), diethylenetriamine; NH2.(CH2)2.NH.(CH2)2.NH2 / 8.92
82 / Pyridine, Azine; / 1.1
83 / 1,1,1-Trifluoropentane-2,4-dione; CF3.CO.CH2.CO.CH3 / 3.18
84 / Cyclopropane-1,1-dicarboxylic acid; C3H4(COOH)2 / 3.5
85 / 3-Methyl-2-oxobutanedioic acid HOOC.CO.CH(CH3).COOH / 3.13
86 / Carboxymethyltartronic acid; / 4.87
87 / b-N-Oxalyl-L-alfa,beta-diaminopropoinic acid, N-oxalylamino-alanine; H2N.CH(COOH).CH2.NH.CO.COOH / 4.74
88 / Pentane-2,4-dione; CH3.CO.CH2.CO.CH3 / 4.7
89 / 4-Ketopentanoic acid; CH3.CO.CH2.CH2.COOH / 1.13
90 / Dimethylmalonic acid; HOOC.C(CH3)2.COOH / 2.2
91 / Ethylpropanedioic acid; HOOC.CH(C2H5).COOH / 2.53
92 / Pentanedioic acid; HOOC.CH2.CH2.CH2.COOH / 1.6
93 / 3-Thiahexane-1,6-dioic acid; HOOC.CH2.S.CH2.CH2.COOH / 1.7
94 / Pyrrolidine-2-carboxylic acid; C4H8N.COOH / 5.27
95 / N-Acetylcysteine; CH3.CO.NH.CH(CH2.SH)COOH / 4.9
96 / 2-Aminopentanedioic acid; H2N.CH(CH2.CH2.COOH)COOH / 5.34
97 / N-Methyliminodiethanoic acid; CH3.N(CH2.COOH)2 / 7.63
98 / 3-(Carboxymethyl)thio-L-alanine; HOOC.CH2.S.CH2.CH(NH2)COOH / 5.12
99 / 4(5)-(2'-Aminoethyl)imidazole; C3H3N2.CH2.CH2.NH2 / 5.21
100 / N-(Phosphonomethyl)iminodiethanoic acid; H2O3P.CH2.N(CH2.COOH)2 / 12.36
101 / 2-Aminopentanedioic acid 5-amide; H2N.CH(CH2.CH2.CO.NH2)COOH / 4.17
102 / Glycyl-alanine; H2N.CH2.CO.NH.CH(CH3).COOH / 3.87
103 / Glycylglycine methyl ester; H2N.CH2.CO.NH.CH2.CO2CH3 / 2.77
104 / Cysteinyl-glycine; H2N.CH(CH2.SH)CO.NH.CH2.COOH / 8.31
105 / 2-Aminopentanoic-5-hydroxamic acid; HOOC.CH(NH2).CH2.CH2.CO.NOH / 7.42
106 / Seryl-glycine; H2N.CH(CH2.OH).CO.NH.CH2.COOH / 3.93
107 / 3-Methyl-butanoic acid, Isovaleric acid; (CH3)2CH.CH2.COOH / 0.96
108 / 2-Amino-3-methylbutanoic acid; H2N.CH(CH(CH3)2)COOH / 4.46
109 / 2-Aminopentanoic acid; CH3.CH2.CH2.CH(NH2).COOH / 4.42
110 / 2-Amino-4-(methylthio)butanoic acid; H2N.CH(CH2.CH2.S.CH3)COOH / 4.39
111 / DL-2-Amino-3-mercapto-3-methylbutanoic acid; (CH3)2C(SH)CH(NH2)COOH / 9.51
112 / 2,5-Diaminopentanoic acid; H2N.CH2.CH2.CH2.CH(NH2)COOH / 6.25
113 / N-Methyldiethanolamine; CH3.N(CH2.CH2.OH)2 / 4.3
114 / N-Methylenedi(phosphonic acid)tetrahydrooxazine; OC4H8N.CH(PO3H2)2 / 9.46
115 / (S,S)-Alanyl-1-aminoethylphosphonic acid; / 4.22
116 / N,N'-Bis(2-hydroxyethyl)aminomethylphosphonic acid; (HO.CH2.CH2)2N.CH2.PO3H2 / 6.3
117 / 1,4,8-triazaoctane, N-(2-Aminoethyl)propane-1,3-diamine; H2NCH2CH2NHCH2CH2CH2NH2 / 8.6
118 / N-(2-Acetamido)iminodiethanoic acid; H2N.CO.CH2.N(CH2.COOH)2 / 7.1
119 / 1-Hydroxycyclopentanecarboxylic acid; HO.C5H8.COOH / 1.89
120 / 1,6-Hexanedioic acid; HOOC.(CH2)4.COOH / 1.8
121 / Isopropylmalonic acid; HOOC.CH(CH(CH3)2).COOH / 2.85
122 / Di(2-Propane-1,3-dioic acid)ether; / 5.62
123 / 2-(Aminomethyl)pyridine; C5H4N.CH2NH2 / 5.2
124 / 3-(4-Imidazolyl)propanoic acid; / 3.23
125 / Cyclobutane-1,1-dicarboxylic acid; C4H6(COOH)2 / 2.53
126 / 2-Hydroxypropane-1,2,3-tricarboxylic acid; HOOCCH2.CH(OH)(COOH).CH2COOH / 5.02
127 / N-Carboxymethyl-L-aspartic acid; / 8.6
128 / Nitrilotriethanoic acid; N(CH2.COOH)3 / 10.66
129 / 2-Amino-3-(4'-imidazolyl)propanoic acid; H2N.CH(CH2.C3H3N2)COOH / 6.61
130 / Glycyl-aspartic acid; H2N.CH2.CO.NH.CH(CH2.COOH).COOH / 3.96
131 / n-Propylmalonic acid; HOOC.CH(C3H7).COOH / 2.75
132 / 2,2'-Thiodipropanic acid; HOOC.CH(CH3).S.CH(CH3).COOH / 2.13
133 / 1,2-Bis(carboxymethylthio)ethane; HOOC.CH2.S.CH2.CH2.S.CH2.COOH / 2.55
134 / 3,3'-Oxodipropionic acid; HOOC.CH2.CH2.O.CH2.CH2.COOH / 2.13
135 / 1,2-Bis(carboxymethoxy)ethane; HOOC.CH2.O.CH2.CH2.O.CH2.COOH / 2.65
136 / D-2,3,4,5-Tetrahydroxy-1,6-hexanedioic acid, Glucaric acid; HOOC.(CHOH)4.COOH / 3.47
137 / 2-Piperidine carboxylic acid; C5H10N.COOH / 6.08
138 / 2,2'-Iminodipropanoic acid; HN(CH(CH3)COOH)2 / 6.6
139 / N-(2-Hydroxyethyl)iminodiethanoic acid; HO.CH2.CH2.N(CH2.COOH)2 / 8.24
140 / N-Carboxymethylthreonine; HOOCCH2NHCH(CH(OH)CH3)COOH / 7.06
141 / 4-(2-Methylaminoethyl)imidazole; / 4.83
142 / Glycyl-glycyl-glycine; H2N.CH2.CO.NH.CH2.CO.NH.CH2.COOH / 3.28
143 / Alanyl-alanine; H2N.CH(CH3).CO.NH.CH(CH3).COOH / 3.75
144 / 1,2-Diaminoethane-N,N'-diethanoic acid; HOOC.CH2.NH.CH2.CH2.NH.CH2.COOH / 10.99
145 / N,N-Dihydroxyhexanediamide; HN(OH).CO.(CH2)4.CO.NH(OH) / 7.76
146 / 4-Methylpentanoic acid; (CH3)2CH.CH2.CH2.COOH / 0.99
147 / 2-Amino-3-methylpentanoic acid; CH3.CH2.CH(CH3).CH(NH2).COOH / 5.29
148 / 2-Amino-4-methylpentanoic acid; H2N.CH(CH2.CH(CH3)2)COOH / 5.29
149 / N,N,N'-Trimethyldiaminoethane-N'-methylphosphonic acid; (CH3)2N.CH2CH2.N(CH3)CH2PO3H2 / 8.41
150 / 1,5,9-Triazanonane, 4-azaheptane-1,7-diamine; H2N.CH2.CH2.CH2.NH.CH2.CH2.CH2.NH2 / 7.94
151 / 2-Aminohexanoic acid (2-Aminocaproic acid) CH3.(CH2)3.CH(NH2).COOH / 4.59
152 / Hexanohydroxamic acid; CH3.CH2.CH2.CH2.CH2.CO.NH.OH / 5.37
153 / 2-Amino-4-(ethylthio)butanoic acid; CH3.CH2.S.CH2.CH2.CH(NH2).COOH / 5.22
154 / N,N-Bis(2-hydroxyethyl)glycine; (HO.CH2.CH2)2N.CH2.COOH / 5.37
155 / 2-Amino-2-deoxy-D-gluconic acid; / 4.56
156 / Fructose-6-phosphoric acid; C6H11O5.H2PO4 / 3.49
157 / 1-Oxa-4,7-diazacyclononane; Cyclo(-((CH2)2.NH)2(CH2)2.O.-) / 6.4
158 / 2,6-Diaminohexanoic acid; H2N.(CH2)4.CH(NH2)COOH / 6.4
159 / 2,6-Diamino-5-hydroxyhexanoic acid; H2N.CH2.CH(OH).CH2.CH2.CH(NH2).COOH / 4
160 / 1-Thia-4,7-diazacyclononane; / 7.54
161 / 1,8-Diamino-3,6-diaza-2,7-octanedione; (H2N.CH2.CO.NH.CH2)2 / 3.95
162 / Tris-(2-hydroxyethyl)amine;; L / 2.05
163 / 1,4,7-Triazacyclononane; cyclo(-NH.CH2.CH2.NH.CH2.CH2.NH.CH2.CH2-) / 11.7
164 / N,N-Bis(2-aminoethyl)glycine; (H2N.CH2.CH2)2N.CH2.COOH / 13.13
165 / 2-Amino-N,N-bis(2-hydroxyethyl)ethylamine; / 5.42
166 / 5-Thia-2,8-diazanonane; / 4.6
167 / 3,6-Dithiaoctane-1,8-diamine; H2N.CH2.CH2.S.CH2.CH2.S.CH2.CH2.NH2 / 4.96
168 / 2-Hydroxy-N,N-bis(2-aminoethyl)ethylamine; / 8.34
169 / N,N'-Dimethyldiaminoethane-N,N'-dimethylphosphonic acid; CH3N(CH2PO3H2).CH2.CH2.N(CH2.PO3H2)CH3 / 13.07
170 / N,N-Dimethyldiaminoethane-N',N'-dimethyldiphosphonic acid; (CH3)2N.CH2CH2.N(CH2PO3H2)2 / 15.04
171 / 1,4,7,10-Tetraazadecane; H2N.CH2.CH2.NH.CH2.CH2.NH.CH2.CH2.NH2 / 11.9
172 / N-Methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid); / 18.01
173 / Ethylenediaminetetra(methylenephosphonous acid); / 7.6
174 / Ethane-1,2-bis(iminobis(methylenephosphonic acid)); ((H2O3PCH2)2NCH2.)2 / 19.1
175 / Benzimidazole; C7H6N2 / 2.45
176 / Benzenecarboxylic acid; C6H5.COOH / 1.06
177 / Bis(imidazol-2-yl)methane; C3H3N2.CH2.C3H3N2 / 5.53
178 / Bis(imidazol-2-yl)methylamine; / 5.38
179 / Cyclopentane-1,1-dicarboxylic acid; C5H8.(COOH)2 / 2.38
180 / Pent-1-ene-5-dioic acid; CH2:CH.CH2.CH2.CH(COOH)2 / 2.62
181 / 1-Amino-2-propanone-N,N-diethanoic acid; CH3.CO.CH2.N(CH2.COOH)2 / 6.89
182 / N-(2'-Carboxyethyl)iminodiethanoic acid; HOOC.CH2.CH2.N(CH2.COOH)2 / 9.98
183 / 4-(2'-Acetylaminoethyl)imidazole; C3H3N2.CH2CH2.NH.COCH3 / 2.55
184 / Histidine methyl ester / 5.04
185 / L-N-Methylhistidine; / 6.37
186 / Glycyl-histamine / 3.58
187 / 1,7-Heptanedioic acid; HOOC.(CH2)5.COOH / 1.3
188 / Butylpropanedioic acid (Butylmalonic acid); HOOC.CH(C4H9).COOH / 2.73
189 / Diethylpropanedioic acid (Diethylmalonic acid); HOOC.C(C2H5)2.COOH / 2.44
190 / 2-Amino-hept-6-enoic acid; CH2:CH.CH2.CH2.CH2.CH(NH2).COOH / 4.45
191 / 2-Propylthiazolidine-4-carboxylic acid; / 2.95
192 / N-Acetyl-penicillamine; CH3.CO.NH.CH(COOH)C(CH3)2SH / 7.01
193 / N-Propyliminodiethanoic acid; CH3.CH2.CH2.N(CH2.COOH)2 / 8
194 / 4-(2-Dimethylaminoethyl)imidazole; / 3.4
195 / Azetidine-1-(2-aminobutanoic acid); / 7.3
196 / 5-Methyhexanoic acid; (CH3)2CH.(CH2)3.COOH / 0.99
197 / 3-(N-Morpholino)propanesulfonic acid; C4H8ON-CH2.CH2.CH2.SO3H / 3.47
198 / 2-Amino-2-deoxy-D-glycero-L-glucoheptonic acid; HOOCCH(NH2)(CHOH)4CH2OH / 4.62
199 / 1-Oxa-4,8-diazacyclodecane; / 5.1
200 / 1-Thia-4,8-diazacyclodecane; / 6.85
201 / 3-[1,1-Dimethyl-2-hydroxyethylamino]-2-hydroxypropanesulfonic acid; / 4.42
202 / 3-[N,N-Bis(2-hydroxyethyl)amino]-2-hydroxypropane sulfonic acid; / 3.83
203 / 3-[N-(Tris(hydroxymethyl)methyl)amino]-2-hydroxypropane sulfonic acid / 3.8
204 / Leucylaminomethylphosphonic acid; / 3.63
205 / 1,4,7-Triazacyclodecane; cyclo(.NHCH2CH2NHCH2CH2NHCH2CH2CH2.) / 11.28
206 / N-(3-Methylbutyl)imino-bis(methylenephosphonic acid); / 9.69
207 / 6-Acetylamino-2-aminohexanoic acid; CH3.CO.NH.(CH2)4.CH(NH2).COOH / 4.51
208 / Glycyl-leucine; H2N.CH2.CO.NH.CH(CH2.CH(CH3)2).COOH / 3.94
209 / N,N'-Dimethylethylenediamine-N,N'-diethanoic acid; / 12.61
210 / N-(2'-Pyridylmethyl)glycine; C5H4N.CH2.NH.CH2.COOH / 7.6
211 / SS-Oxydisuccinic acid; O(CH(COOH)CH2.COOH)2 / 6.62
212 / 1-Hydroxy-3-oxapentane-1,2,4,5-tetracarboxylic acid; HO.CH(COOH).CH(COOH).O.CH(COOH).CH2(COOH) / 6.31
213 / 2-(n-Propyl)pyridine; C5H4N.CH2.CH2.CH3 / 1.3
214 / Amino-di(butanedioic acid);HN(CH(COOH)CH2.COOH)2 / 10.3
215 / Acetyl-L-histidine; / 2.91
216 / 2-Aminomethyl-N-2'-hydroxyethylpyridine; C5H4N.CH2.NH.CH2.CH2.OH / 5.2
217 / Glycylglycine-N,N-diethanoic acid; (HOOC.CH2)2N.CH2.CO.NH.CH2.COOH / 7.94
218 / Glycyl-histidine; H2N.CH2.CO.NH.CH(CH2.C3H3N2).COOH / 3.91
219 / Histidyl-glycine; H2N.CH(CH2.C3H3N2).CO.NH.CH2.COOH / 5.15
220 / Cyclohexane-1,1-dicarboxylic acid; C6H10.(COOH)2 / 2.26
221 / Hex-1-ene-6-dioic acid; CH2:CH.CH2.CH2.CH2.CH(COOH)2 / 2.68
222 / L-trans-Cyclohexane-1,2-dicarboxylic acid; C6H10.(COOH)2 / 2.3
223 / 2-Mercapto-1-aminoethane-N,N,S-triethanoic acid; HOOC.CH2.S.CH2.CH2.N(CH2COOH)2 / 10.92
224 / N-Dimethylhistidine; (CH3)2N.CH(CH2.C3H3N2).COOH / 6.34
225 / Azetidine-2-carboxy-1-(2-aminobutaneoic acid) / 10.25
226 / B-Alanyl-histamine; NH2.CH2.CH2.CO.NH.CH2CH2.C3H3N2 / 3.53
227 / Sarcosyl-histamine / 3.08
228 / 3,6,9-Trithiaundecanedioic acid; HOOC.CH2.S.C2H4.S.C2H4.S.CH2.COOH / 2.25
229 / Di(carboxymethoxy)ethyl ether; (HOOC.CH2.O.CH2.CH2)2O / 2.6
230 / N-Butyliminodiethanoic acid; C4H9.N(CH2.COOH)2 / 8.12
231 / 2-(D-Arabinosyl)thiazolidine-4-carboxylic acid; / 4.19
232 / N,N-Dihydroxyoctanediamide; HN(OH).CO.(CH2)6.CO.NH(OH) / 8.05
233 / 2,7-Dicarboxy-3,6-diaza-1,8-octanedithiol; HS.CH2.CH(COOH)NH.CH2CH2.NH.CH(COOH)CH2.SH / 20.98
234 / 1,9-Dicarboxy-2,8-diaza-5-oxanonane (HOOC.CH2.NH.CH2.CH2)2O / 10.15
235 / 6-Methylheptanoic acid; (CH3)2CH.C(CH2)4.COOH / 1.02
236 / 3,6,9-Triazaundecanedioic acid; (HOOC.CH2.NH.CH2.CH2)2NH / 13.29
237 / 4,7-Dimethyl-1-oxa-4,7-diazacyclononane; / 6.58
238 / 1,7-Dioxo-4,10-diazacyclododecane; / 6.51
239 / N,N-Bis(2-hydroxyethyl)piperazine; / 2.67
240 / N,N'-Bis(2-carbamoylethyl)-1,2-diaminoethane; / 5.05
241 / 1-(N-L-Leucylamino)ethanephosphonic acid; H2NCH(CH2CH(CH3)2)CONHCH(CH3)PO3H2 / 3.76
242 / 1,4,8-Triazacycloundecane; cyclo(-NH.C2H4.NH.C3H6.NH.C3H6-) / 10.41
243 / 1-Oxa-4,7,10-triazacyclododecane; / 10.53
244 / 1-(2-Aminoethylamino)-1-deoxy-D-galactitol; NH2.(CH2)2.NH.CH2.(CHOH)4.CH2OH / 5.13
245 / 1,4,7,10-Tetraazacyclododecane; cyclo(-(NH.CH2.CH2.)4-) / 16.2
246 / 1,4-Bis(2-aminoethyl)-1,4-diazacyclohexane; NH2.CH2CH2.N(CH2CH2)2N.CH2CH2.NH2 / 5.81
247 / 1,4,10,13-Tetraaza-7-oxatridecane; / 10.97
248 / 1,4,10,13-Tetraaza-7-thiatridecane; / 11.24
249 / 3,3-(Bis(imidazol-2-yl))propanoic acid; / 5.71
250 / 3-Phenylpropanoic acid; C6H5.CH2.CH2.COOH / 1.14
251 / 2-Amino-3-phenylpropanoic acid; H2N.CH(CH2.C6H5)COOH / 4.63
252 / 3-Amino-3-phenyl-propanoic acid; H2N.CH(C6H5).CH2.COOH / 4.65
253 / 2-Amino-3-(4-hydroxyphenyl)propanoic acid; HO.C6H4.CH2.CH(NH2).COOH / 6.2
254 / 2-Amino-N-hydroxy-3-phenylpropanamide, phenylalanine hydroxamic acid; C6H5.CH2.CH(NH2).CO.NHOH / 4.92
255 / 2,3-Diaminopropanoic-N,N'-di-1,3-propanedioic acid; (HOOC)2CH.NH.CH(COOH).CH2.NH.CH(COOH)2 / 11.78
256 / Cytidine-5'-monophosphoric acid, Cytidilic acid; / 2.42
257 / 3-Alanyl-histidine; H2N.CH2.CH2.CO.NH.CH(CH2.C3H3N2).COOH / 4.05
258 / Alanyl-histidine; / 4.31
259 / Cytidine-5'-diphosphoric acid; / 4.1
260 / 1,4-Diazacycloheptane-N,N'-diethanoic acid; / 7.98
261 / Azetidine-2-carboxy-1-(2-aminopentanoic acid); / 7.25
262 / Cytidine-5'-triphosphoric acid; / 5.09
263 / Dipropylpropanedioic acid (Di-n-propylmalonic acid); / 2.5
264 / N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-3-aminopropanoic acid; / 1.75
265 / 2-(D-Deoxyglucosyl)thiazolidine-4-carboxylic acid; / 2.81
266 / 2(RS)-1,2,3,4,5-Pentahydroxypentylthiazolidine-4(R)-carboxylic acid; / 3.75
267 / 1,4-Dioxa-7,11-diazacyclotridecane; / 4.89
268 / N-(2-Hydroxyethyl)piperazine-N'-(2-hydroxypropanesulfonic acid); / 4.13
269 / 1,5,9-Triazacyclododecane; cyclo(-NH.(CH2)3.NH.(CH2)3.NH.(CH2)3-) / 8.41
270 / 1-Oxa-4,7,11-triazacyclotridecane; cyclo(-O.(CH2.CH2.NH)2.CH2.CH2.CH2.NH.CH2.CH2-) / 9.8
271 / 1,4,7,10-Tetraazacyclotridecane; cyclo(-(NH.CH2.CH2.)4.CH2-) / 15.6
272 / N,N'-Bis(2-aminoethyl)-1,4-diazacycloheptane; / 10.18
273 / 1,4,7-Triazacyclononane-1,4,7-triyltrimethylenetris(phosphinic acid); / 13.04
274 / 1,5,9,13-Tetraazatridecane; H2N.(CH2)3.NH.(CH2)3.NH.(CH2)3.NH2 / 9.3
275 / Tris-(3-aminopropyl)amine; / 10.7
276 / 3-Benzoyl-1,1,1-trifluoroacetone; CF3.CO.CH2.CO.C6H5 / 3.6
277 / 2-Pyridylmethyliminodiethanoic acid; C5H4N.CH2.N(CH2.COOH)2 / 8.78
278 / 4-Phenylbutanoic acid; C6H5.CH2.CH2.CH2.COOH / 1.09
279 / 2-(N-(2-Hydroxybenzyl))aminopropanoic acid; HO.C6H4.CH2.NH.CH(CH3)COOH / 8.75
280 / Deoxyguanosine-5'-monophosphoric acid; / 2.99
281 / Guanosine-5'-monophosphoric acid; / 2.65
282 / (1-Methylaminoethyl)benzyl alcohol; C6H5.CH(OH)CH(CH3)NHCH3 / 5.13
283 / Triglycine-N,N-diethanoic acid; (HOOC.CH2)2N.CH2.CO-Gly-Gly-OH / 7.63
284 / Inosine 5'-triphosphoric acid; / 5.32
285 / N-(Imidazole-4-ylmethyl-5-methyl)histamine; / 8.28
286 / 1,2-Diaminoethane-N,N'-di-1,4-butanedioic acid; (CH2.NH.CH(COOH)CH2.COOH)2 / 13.58
287 / N-Benzyliminodiethanoic acid; C6H5.CH2.N(CH2.COOH)2 / 6.98
288 / N-(2-Hydroxybenzyl)iminodiethanoic acid; HO.C6H4.CH2.N(CH2.COOH)2 / 12.99
289 / 5-Phenylpentanoic acid; / 1.13
290 / Bis-(2-aminoethylether)-N,N'di(1,3-propanedioic acid); ((HOOC)2CH.NH.CH2.CH2)2O / 10.53
291 / Guanosine-5'-triphosphoric acid; / 5.52
292 / N,N'-Bis(4'-(5')-imidazolylmethyl)-1,2-diaminoethane; / 10.39
293 / 2-(5-Carboxy-1,2,3,4-tetrahydroxypentyl)4-carboxythiazolidine, Galactocarboxythiazolidine; / 4.08
294 / 1,5-Diazacyclooctane-N,N'-diethanoic acid; / 11.07
295 / Pyrrolidine-2-carboxy-1-(2-aminopentanoic acid); / 7.3
296 / 1-Thia-4,7-diazacyclononane-N,N'-diethanoic acid; / 14.03
297 / 1-Oxa-4,7-diazacyclononane-N,N'-diethanoic acid; / 12.53
298 / N-(Hydroxyethyl)diaminoethane-N,N',N'-triethanoic acid; / 14.42
299 / 1,12-Dicarboxy-2,5,8,11-tetraoxadodecane; (HOOC.CH2.O.CH2.CH2.O.CH2)2 / 2.18
300 / N-(Isobutyroyl)-lysine; (CH3)2CH.CO.NH.(CH2)4.CH(NH2)COOH / 4.89
301 / N,N-Dihydroxydecanediamide; HN(OH).CO.(CH2)8.CO.NH(OH) / 8.8
302 / Glycyl-lysyl-epsilon-glycine; / 4.82
303 / 1,4,7-Trioxa-10,13-diazacyclopentadecane; / 5.04
304 / 4,7,13-Trioxa-1,10-diazacyclopentadecane (Trioxa(2,1)cryptand); / 5.34
305 / 1,4,7,10-Tetraaza-bicyclo[8.2.2]tetradecane; / 10.95
306 / 1-Oxa-4,8,12-triazacyclotetradecane; / 11.52
307 / 1,4-Dioxa-7,10,13-triazacyclopentadecane; / 8.95
308 / R-2,2'-(1,2-Ethandyldiimino)-bis-1-butanol; / 6.22
309 / 4,10-Bis(phosphonomethyl)-1,7-dioxa-4,10-diazacyclododecane; / 12.97
310 / 1,4,7,11-Tetraazacyclotetradecane; cyclo(-(HNCH2.CH2)3.CH2.NH.CH2.CH2.CH2-) / 15.44
311 / 1,4,8,11-Tetraazacyclotetradecane; cyclo(-(HN.CH2.CH2.NH.(CH2)3)2-) / 15.28
312 / 1,4-Bis(3-aminopropyl)-1,4-diazacyclohexane, 1,4-Bis(3-aminopropyl)-piperazine; / 6.32
313 / 1,5-Bis(2-aminoethyl)-1,5-diazacyclooctane; NH2.CH2CH2.N(CH2CH2CH2)2N.CH2CH2.NH2 / 12.81
314 / 1-Oxa-4,7,10,13-tetraazacyclopentadecane; / 13.21
315 / 1,4,7,10,13-Pentaazacyclopentadecane; cyclo(-(HN.CH2.CH2)5-) / 19.1
316 / 1,4,7,10-Tetraazacyclododecane-1,7-bis(methanephosphonic acid); / 21.2
317 / N,N,N',N'-Tetra-(2-aminoethyl)diaminoethane; / 16.15
318 / 2-Amino-3-(3-indolyl)propanoic acid; H2N.CH(CH2.C8H6N)COOH / 5.16
319 / N,N,S-Tris(carboxymethyl)methionine; / 8.78
320 / 1,3-Diamino-2-hydroxypropane-N,N,N',N'-tetraethanoic acid; / 13.7
321 / 3,6,9,15-Tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene; / 14.4
322 / 1-Thia-4,8-diazacyclodecane-N,N'-diethanoic acid; / 14.41
323 / 2,2-Dibutylpropanedioic acid; HOOC.C(C4H9)2.COOH / 2.52
324 / 1,1,1-Tris(aminomethyl)ethane-N,N',N''-triethanoic acid; / 12.78
325 / 1-(2-Hydroxyethyl)-1,5,9-triazacyclododecane; / 7.6
326 / 4,7,10-Trimethyl-1-oxa-4,7,10-triazacyclododecane; / 10
327 / 1,4-Dioxa-7,11,14-triazacyclohexadecane; / 8.1
328 / 1,4,8,12-Tetraazacyclopentadecane; cyclo(-(NH.CH2.CH2.(N.(CH2)3.)3-) / 15
329 / N,N'-Bis(2-aminopropyl)-1,4-diazacycloheptane; / 8.17
330 / 1-(3-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane; / 13.7
331 / 1-Oxa-4,7,11,14-tetraazacyclohexadecane; / 11.72
332 / 1,4,7,10,13-Pentaazacyclohexadecane; cyclo(-(NH.CH2.CH2)5.CH2-) / 17.9
333 / 1,4-Dioxa-7,11,15-triazacycloheptadecane; / 7.09
334 / 1,4,7-Tris(hydroxyethyl)-1,4,7-triazacyclononane / 12.07
335 / 2,2',2",2"'-(Trimethylenedinitrilo)tetrakis(ethylamine); / 14.86
336 / 1,10-Phenanthroline; / 6.4
337 / bis-((2-Pyridyl)methyl)-amine (Di-2-picolylamine); C5H4N.CH2NHCH2.C5H4N / 7.57
338 / 3,6-Dioxaoctane-1,2,4,5,7,8-hexacarboxylic acid; (CH2(COOH).CH(COOH).O.CH(COOH)-)2 / 8.07
339 / 1-Hydroxy-4-methylphenyl-2-methyleneiminodiethanoic acid; / 13.1
340 / Alanyl-phenylalanine; H2N.CH(CH3)CO.NH.CH(CH2.C6H5)COOH / 3.29
341 / Histidyl-histidine; H2N.CH(CH2.C3H3N2).CO.NH.CH(CH2.C3H3N2).COOH / 4.23
342 / Aspartyl-aspartyl-aspartic acid; / 4.55
343 / 1-Carboxy-1,3-diaminopropane-N,N,N',N'-tetraethanoic acid; (HOOCCH2)2NCH(COOH)(CH2)2N(CH2COOH)2 / 16.94
344 / Tetraglycine-N,N-diethanoic acid; (HOOC.CH2)2N.CH2.CO.Gly-Gly-Gly-OH / 7
345 / Azetidine-2-carboxy-1-(4-azaheptane-1,5-dicarboxylic acid); / 10.5
346 / 1,2-Diaminoethane-N,N'-di(2-pentane-1,5-dioic acid); (CH2NHCH(COOH)CH2CH2COOH)2 / 10.25
347 / 2,2'-Thiobis(ethyliminodiethanoic acid); S(CH2.CH2.N(CH2.COOH)2)2 / 13.4
348 / Oxa-bis(ethyleneimino)diethanoic acid; ((HOOC.CH2)2N.CH2.CH2)2O / 15.3
349 / 3,7,10,16-Tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene; / 14.27
350 / 1,9-Bis(4-imidazolyl)-2,8-diaza-5-oxanonane; / 9.52
351 / 1,4,7-Triazacyclononane-N,N',N"-triethanoic acid; / 18.3
352 / Azetidine-2-carboxy-1-(4-azaheptane-1-amino-1,5-dicarboxylic acid); / 15.4
353 / 1,9-Bis(4-imidazolyl)-2,5,8-triazanonane; / 13.3
354 / 1,7-Dioxa-4,10-diazacyclododecan-4,10-diethanoic acid; / 12.27
355 / 7,10-Diaza-1,4-Dioxacyclododecane-7,10-diethanoic acid; / 12.52
356 / 1-Oxa-4,7,10-triazacyclododecan-4,10-diethanoic acid; / 16.12
357 / 1-Amino-8-methyl-1,5,9-tricarboxy-4,8-diazadecane; / 13.7
358 / 1,4,7,13-Tetraoxa-10,16-diazacyclooctadecane; / 4.26
359 / 4,7,13,16-Tetraoxa-1,10-diazacyclooctadecane; / 3.77
360 / 1,4,10-Trioxa-7,13-diazacyclopentadecane-7,13-diyldimethylenediphosphonic acid; / 13.1
361 / 1,4,7,10-Tetramethyl-1,4,7,10-tetraazacyclododecane; / 14.04
362 / 1,5,9,13-Tetraazacyclohexadecane; cyclo(-(NH.CH2.CH2.CH2)4-) / 13.02
363 / 1-(3-Aminopropyl)-1,5,9-triazacyclododecane; / 11.7
364 / 1-(2-Hydroxyethyl)-1,4,8,11-tetraazacyclotetradecane; / 10.3
365 / 1,10-Dioxa-4,7,13,16-tetraazacyclooctadecane; / 10.51
366 / 1,4-Dioxa-7,10,13,16-Tetraazacyclooctadecane; / 9.52
367 / 1,4,7,11,14-Pentaazacycloheptadecane; cyclo(-(NH.C2H4)3.CH2(NH.C2H4)2.CH2-) / 15.8
368 / 1,4,7,10,13,16-Hexaazacyclooctadecane; cyclo(-(NH.CH2.CH2)6-) / 18.7
369 / 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetrayltetramethylenetetrakis(phosphinic acid); / 14.6
370 / 2,5,8,11,14,17-Hexaazaoctadecane; CH3.NH.(CH2)2.NH.(CH2)2.NH.(CH2)2.NH.(CH2)2.NH.C(CH2)2.NH.CH3 / 14.02
371 / 5-Ethyl-5-(4-amino-2-azabutyl)-1,9-diamino-3,7-diazanonane; / 16.4
372 / 2-Methyl-1,10-phenanthroline; / 4.96
373 / 2-Benzylnitrilotriethanoic acid; / 10.24
374 / Glycyltrytophan; / 3.3
375 / 3,7,11,17-Tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene; / 12.81
376 / N-Acetyl-cysteinyl-prolinyl-cysteine amide; CH3CONHCH(CH2SH)COC4H7NCONHCH(CH2SH)CONH2 / 9.31
377 / N,N'-Bis(5-methylimidazol-4-ylmethyl)-1,3-diaminopropan-2-ol; / 9.63
378 / 1,11-Dioxa-4,8-diazacyclotridecane-N,N'-diethanoic acid; / 10.26
379 / N-Acetyl-cysteinyl-valinyl-cysteine amide; CH3CONHCH(CH2SH)CONHCH(CH(CH3)2)CONHCH(CH2SH)CONH2 / 9.39
380 / 4,8,12-Trimethyl-1-oxa-4,8,12-triazacyclotetradecane; / 6.36
381 / 1-(3-Hydroxypropyl)-1,4,8,11-tetraazacyclotetradecane; / 13
382 / 2,9-Dimethyl-1,10-phenanthroline; / 4.1
383 / N,N'-Bis-(2-pyridylmethyl)-1,2-diaminoethane; (C5H4N.CH2.NH.CH2)2 / 11.13
384 / 2-(Benzylamino)-2-deoxy-D-glycero-D-gulo-heptonic acid; / 3.88
385 / 1-Carboxy-1,5-diaminopentane-N,N,N',N'-tetraethanoic acid; (HOOCCH2)2NCH(COOH)(CH2)4N(CH2COOH)2 / 13.3
386 / Alanyl-alanyl-aspartyl-aspartic acid; / 3.77
387 / Alanyl-aspartyl-alanyl-aspartic acid; / 3.84
388 / Alanyl-aspartyl-aspartyl-alanine; / 3.69
389 / Aspartyl-alanyl-alanyl-aspartic acid; / 4.88
390 / Aspartyl-alanyl-histidine-N-methylamide; / 4.17
391 / Diethylenetriamine-pentaethanoic acid; HOOC.CH2.N(CH2.CH2.N(CH2.COOH)2)2 / 18.29
392 / 1,6-Diaminohexane-N,N,N',N'-tetraethanoic acid; ((HOOC.CH2)2N.CH2.CH2.CH2)2 / 12.64
393 / Diaminoethane-N,N,N',N'-tetrapropanoic acid; (HOOC.CH2CH2)2N.CH2CH2.N(CH2CH2.COOH)2 / 9.31
394 / Ethyleneglycol-O,O'-bis(2-aminoethyl ether)-N,N,N',N'-tetraethanoic acid; / 14.4
395 / 7-Methyl-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene; / 11.91
396 / Azetidine-2-carboxy-1-(1-amino-5-azadecane-1,6-dicarboxylic acid); / 9.3
397 / 1-Oxa-4,7,10-triazacyclododecane-4,7,10-triethanoic acid; / 18.66
398 / N,N-Bis(2-aminoethyl)ethylamine-N',N',N",N"-tetraethanoic acid; / 17.18
399 / 1,11-Bis(2-imidazolyl)-2,6,10-triazaundecane; / 11.9
400 / 1,11-Bis(4-imidazolyl)-2,6,10-triazaundecane; / 11.83
401 / 1,4,10,13-Tetraoxa-7,16-diaza-2,3-dicarboxycyclooctadecane; / 5.1
402 / 1,4,7,10-Tetraazacyclododecane-1,4,7-triethanoic acid; / 21.87
403 / Hexanoic acid bis(3-hydroxycarbamoyl-propyl)amide; HONHCO(CH2)3NHCO(CH2)4CONH(CH2)3COHNOH / 8.49
404 / 1-Oxa-4,8,12-triazacyclotetradecane-4,12-diethanoic acid; / 12.59
405 / 1,10-Diaza-4,7,13,18-tetraoxabicyclo[8,5,5]eicosane (2,1,1); / 6
406 / 1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7-ethanoic acid; / 5.44
407 / 7,13-Bis(2-hydroxyethyl)-1,4,10-trioxa-7,13-diazacyclopentadecane / 6.18
408 / 1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diyldimethylenediphosphonic acid; / 9.34
409 / 1,4,8,11-Tetramethyl-1,4,8,11-tetraazacyclotetradecane; / 10.4
410 / 1,4-Bis(3-hydroxypropyl)-1,4,7,10-tetraazacyclododecane; / 12.3
411 / 1,4-Dioxa-7,10,13,16,19-pentaazacycloheneicosane; / 12.89
412 / 1,10-Dimethyl-1,4,7,10,13,16-hexaazacyclooctadecane; / 15.67
413 / N,N,N',N'-Tetrakis(3-aminopropyl)diaminoethane; (-CH2.N(CH2.CH2.CH2.NH2)2)2 / 10.53
414 / 1,4,7,10,13,16,19-Heptaazacycloheneicosane; / 13.33
415 / 2,5,8,11,14,17,20-Heptaazaheneicosane; CH3.(NH.(CH2)2)6.NH.CH3 / 13.52
416 / 1,4-Bis(1,4,7-triaza-1-cyclononyl)butane; C6H14N3.(CH2)4.C6H14N3 / 17.76
417 / 1,4,7,13-Tetramethyl-1,4,7,10,13,16-hexaazacyclooctadecane; / 13.29
418 / 1,4,7,13,16,19-Hexaaza-10,22-dioxacyclotetracosane; / 10.66
419 / 7,10,13-Tris(2-aminoethyl)-1,4-dioxa-7,10,13-triazacyclopentadecane; / 12.15
420 / N-(Hydroxobenzyl)diaminoethane-N,N',N'-triethanoic acid; HO.C6H4.CH2.N(CH2COOH)CH2CH2.N(CH2COOH)2 / 16.93
421 / N,N'-Bis-(2-pyridylmethyl)-1,3-diaminopropane; (C5H4N.CH2.NH.CH2)2CH2 / 10.33
422 / N,N'-Bis(imidazole-4-ylmethyl-5-methyl)histamine; / 12.73
423 / 1,2,3-Tris(N,N-bis(carboxymethyl)amino)propane; / 15.8
424 / 1,5,9-Triazacyclododecane-N,N',N"-triethanoic acid; / 19
425 / Pyrrolidine-2-carboxy-N-(1-amino-1,6-dicarboxy-5-azanonane); / 8.8
426 / 4,7,11-Tris(carboxymethyl)-1-oxa-4,7,11-triazacyclotridecane; / 17.56
427 / N'-(2-Hydroxypropyl)-diethylenetriamine-N,N,N",N"-tetraethanoic acid; / 15.92
428 / 1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7-malonic acid; / 4.87
429 / Tris(4-Carboxy-3-methyl-3-azabutyl)amine; N(CH2.CH2.N(CH3).CH2.COOH)3 / 14.03
430 / 2,12-Dimethyl-5,9-di(methylcarboxy)-2,5,9,12-tetraazatridecane / 13.6
431 / 1-(2-Hydroxyethyl)-4,8,11-trimethyl-1,4,8,11-tetraazacyclotetradecane; / 9.2
432 / 1,3-Bis(1,4,7-triaza-1-cyclononyl)propane; C6H14N3.(CH2)3.C6H14N3 / 18.99
433 / N,N'-Dimethyl-1,10-phenanthroline-2,9-dimethanamine; / 8.98
434 / 1,2-Bis(2'-hydroxybenzylamino)ethane; (HO.C6H4.CH2.NH.CH2.)2 / 11.97
435 / 1-Phenyl-ethylenediamine-N,N,N',N'-tetraethanoic acid (DL) / 16.46
436 / N,N-Bis-(2-pyridyl-methyl)-1,4-diaminobutane; (C5H4N.CH2.NH.CH2.CH2)2 / 7.68
437 / 1,9-Bis(2-pyridyl)-2,8-diaza-5-oxanonane; / 9.52
438 / Bis(2-(2-pyridylmethylamino)ethyl) sulfide; (C5H4N.CH2.NH.CH2.CH2.)2S / 10.64
439 / 1,9-Bis-(2-pyridyl)-2,5,8-triazanonane; (C5H4N.CH2.NH.C2H4)2NH / 13.71
440 / N-Acetyl-cysteinyl-prolinyl-histidine amide; CH3CONHCH(CH2SH)COC4H7NCONHCH(CH2C3H3N2)CONH2 / 5.61
441 / 1,4,10,13-Tetraoxa-7,16-diaza-2,3,11,12-tetracarboxycyclooctadecane; / 7.7
442 / 1,4,10,13-Tetraoxa-7,16-diaza-2,3,7,16-tetracarboxycyclooctadecane; / 10.2
443 / 1,8-Diaminooctane-N,N,N',N'-tetraethanoic acid; ((HOOCCH2)2N(CH2)4)2 / 12.6
444 / 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraethanoic acid; / 20.52
445 / 4,8,12-Tris(carboxymethyl)-1-oxa-4,8,12-triazacyclotetradecane; / 12.85
446 / 1,4-Dioxa-7,10,13-triazacyclopentadecane-7,10,13-triethanoic acid; / 16.82
447 / 1,7-Dioxa-4,10,13-triazacyclopentadecane-N,N',N"-triethanoic acid; / 16.38
448 / N'-(2-Hydroxypropyl)di(carboxymethyl)triazadodecanedioic acid; / 15.03
449 / Diethylenetriaminepentaethanoic acid N,N'-bismethylamide; / 12.04
450 / 1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-N,N'-diethanoic acid; / 8.96
451 / 1,2-Diaminoethane-N,N'-bis(2-propylethanoamide)-N,N'-diethanoic acid;(Me2CHNHCOCH2N(CH2COOH)CH2)2 / 9.74
452 / 1,10-Diaza-4,7,13,16,21-pentaoxabicyclo[8,8,5]tricosane (2,2,1); / 5.41
453 / Tetrakis(2-aminoethyl)-a,a'-diamino-4-xylene; C6H4.(CH2.N(CH2.CH2.NH2)2)2 / 10.05
454 / 2,6-Bis[(bis(2-aminoethyl)amino)methyl]phenol; / 14.92
455 / N,N'-Bis(2-hydroxypropyl)-1,4,10-trioxa-7,13-diazacylopentadecane; / 6.5
456 / N,N'-Bis(2-hydroxyethyl)-1,7,10,16-tetraoxa-4,13-diazacyclooctadecane; / 3.03
457 / 4,7-Dimethyl-1,4,7,10-tetraaza-13,18-dioxabicyclo[8,5,5]eicosane; / 11.2
458 / 1,11-Bis(2-hydroxyethyl)-4,8-dimethyl-1,4,8,11-tetraazacyclotetradecane; / 9.43
459 / 1,4-Bis(2-hydroxyethyl)-8,11-dimethyl-1,4,8,11-tetraazacyclotetradecane; / 9.6
460 / 1,4,7,10-Tetrakis(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane; / 12.8
461 / 2,5,8,11,14,17,20,23-Octaaza-tetracosane; / 15.19
462 / N,N'-Bis(2-hydroxybenzyl)propane-1,3-diamine; / 11.04
463 / 3,6,9,15-Tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triethanoic acid; / 18.22
464 / 1,4,7,10-Tetraazacyclotridecane-1,4,7,10-tetraethanoic acid; / 19.13
465 / 1,4-Dioxa-7,10,14-triazacyclohexadecane-7,10,14-triethanoic acid; / 12.71
466 / 10-Hydroxypropyl-1,4,7,10-tetraazacyclododecane-1,4,7-triethanoic acid; / 20.4
467 / 1,4,7,10-Tetraazacyclododecane-1,4,7-tri(2-hydroxymethylethanoic acid); / 17.2
468 / 2,12-Dimethyl-5,9-di(2-carboxyethyl)-2,5,9,12-tetraazatridecane; / 7.32
469 / 4,7,10-Tri-(2-hydroxypropyl)-1-oxa-4,7,10-triazacyclododecane; / 9.92
470 / 1,4,8-Tris(2-hydroxyethyl)-11-methyl-1,4,8,11-tetraazacyclotetradecane; / 8.5
471 / 1,5-Bis(1,4,7-triaza-1-cyclononyl)pentane; / 14.81
472 / 10,13,16-Trimethyl-1,4-dioxa-7,10,13,16,19-pentaazacycloheneicosane; / 10.71
473 / 1,4,7-Trimethyl-1,4,7,10,13,16,19-heptaazacyclohenicosane; / 10.69
474 / Tris(2-pyridylmethyl)amine; (C5H4NCH2)3N / 10.88
475 / 2,5,8-Triaza[9]-[9](2,9)[1,10]-phenanthrolinophane; / 16.15
476 / N,N'-Bis(2-pyridylmethyl)diaminoethane-N,N'-diethanoic acid; / 15.2
477 / 1,9-Diphenyl-2,5,8-triazanonane; / 6.6
478 / 1,9-Bis(2-hydroxyphenyl)-2,5,8-triazanonane; / 16.47
479 / N'-(2-Pyridylmethyl)-diethylenetriamine-N,N,N",N"-tetraethanoic acid; / 17.96
480 / 1,11-Bis-(2-pyridyl)-2,6,10-triazaundecane; (C5H4N.CH2.NH.C3H6)2NH / 11.18
481 / 7-Methyl-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-3,11-diethanoic acid; / 14.01
482 / N-Acetyl-cysteinyl-valinyl-histidine ethyl ester; / 6.7
483 / Triethylenetetraaminehexaethanoic acid;((HOOC.CH2)2N.CH2.CH2.N(CH2.COOH).CH2)2 / 18.3
484 / 1,4,8,11-Tetraazacyclotetradecane-1,4,8,11-tetraethanoic acid; / 16.39
485 / 1,7,13-Trioxa-4,10,16-triazacyclooctadecane-N,N',N"-triethanoic acid; / 9.89
486 / N,N',N"-Tris[2(S)-hydoxybutanoic acid]-1,4,7-triazacyclononane; / 14.32
487 / 1,2-Diaminoethane-N,N'-bis(t-butylethanoamide)-N,N'-diethanoic acid;Me3CNHCOCH2N(CH2COOH)CH2)2 / 9.67
488 / 10-[2,3-Dihydroxy-(1-hydroxymethyl)-propyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triethanoic ac.; / 17
489 / 1,10-Diaza-4,7,13,16,21,24-hexaoxabicyclo[8,8,8]hexacosane (2,2,2); / 2.8
490 / 7,16-Di(2-hydroxypropyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane; / 3
491 / N,N',N",N"'-Tetrakis(2-hydroxyethyl)-1,4,8,11-tetraazacyclotetradecane; / 6.43
492 / 1,6-Bis(1,4,7-triaza-1-cyclononyl)hexane; / 15.2
493 / 1,4,7,10,13,16,21,24-Octaaza-bicyclo[8.8.8]hexacosane; N(CH2CH2NCH2CH2NCH2CH2)3N / 12.68
494 / 2,5,8,11,14,17,20,23,26-Nonaaza-heptacosane; / 14.8
495 / N'-(2-Pyridylmethyl)di(carboxymethyl)triazadodecanedioic acid; / 17.14
496 / 1,13-Bis(2-pyridyl)-2,5,9,12-tetraazatridecane; C5H4N.CH2NHC2H4NHC3H6NHC2H4NHCH2.C5H5N / 17.89
497 / 1,4,8,12-Tetrazacyclopentadecane-N,N',N'',N'''-tetraethanoic acid; / 16.04
498 / 4-Methyl-1,4,10-triaza-7,13,16,21,24-pentaoxa-bicyclo[8,8,8]hexacosane; / 6.3
499 / 7,10,13-Tris(2-hydroxypropyl)-1,4-dioxa-7,10,13-triazacyclopentadecane; / 7.21
500 / N,N',N",N"'-Tetrakis(2-hydroxyethyl)-1,4,8,12-tetraazacyclopentadecane; / 4.5
501 / 1,7-Bis(1,4,7-triaza-1-cyclononyl)heptane; / 15.2
502 / 13,16,19-Trimethyl-1,4,7-trioxa-10,13,16,19,22-pentaazacyclotetracosane; / 10.13
503 / N,N'-Di-(2-hydroxybenzyl)-diaminoethane-N,N'-diethanoic acid; / 18.95
504 / 2,5,8,11-Tetraaza[12]-[12](2,9)[1,10]-phenanthrolinophane; / 14.29
505 / 1,12-Diphenyl-2,5,8,11-tetraazadodecane; / 10.47
506 / 3,7,15,19,25,26-Hexaazatricyclo[19.3.1.1]hexacosa-1(25),9,11,13(26),21,23-hexaene; / 15.83
507 / 1,14-Bis(2-pyridyl)-2,6,9,13-tetraazatetradecane; C5H4N.CH2NHC3H6NHC2H4NHC3H6NHCH2.C5H5N / 16.33
508 / Diethylenetriamine-N,N,N',N",N"-pentaethanoic acid bis(isopropylamide); / 12.31
509 / 10-(2-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-tris(2-hydroxymethylethanoic acid); / 17.16
510 / 1,4,7,10-Tetrakis(methylcarbamoylmethyl)-1,4,7,10-tetraazacyclododecane; / 13
511 / 4,7-Dimethyl-1,4,7,10-tetraaza-13,16,21,24-tetraoxa-bicyclohexacosane; / 6
512 / 1,3-Bis(2,5,8,11-tetraazaundecyl)benzene; / 12.2
513 / 1,4,7,10-Tetra-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane; / 13.45
514 / 1,4,7,10-Tetrakis(3-hydroxypropyl)-1,4,7,10-tetraazacyclododecane; / 8.3
515 / 4,7,13,16-Tetrakis(2-hydroxyethyl)-1,10-dioxa-4,7,13,16-tetraazacyclooctadecane; / 5.9
516 / 1,8-Bis(1,4,7-triaza-1-cyclononyl)octane; / 14.84
517 / 1,15-Dioxa-4,8,12,18,22,26-hexaazacyclooctacosane; / 8.21
518 / 1,4,7,16,19,22-Hexaaza-10,13,25,28-tetraoxacyclotriacontane; / 8.31
519 / N-Acetyl-histidinylprolinylhistidine ethylester;CH3CONHCH(CH2C3H3N2)COC4H7NCONHCH(CH2C3H3N2)CONH2 / 3.29
520 / N'-(2-Hydroxy-2-phenylethyl)di(carboxymethyl)triazadodecanedioic acid; / 17.37
521 / N,N',N"-Tris[2(S)-hydroxybutanoic acid]-1,5,9-triazacyclododecane; / 6.98
522 / N,N"-2-Bis(2-pyridylmethyl)diethylenetriamine-N,N',N"-triethanoic acid; / 14.02
523 / 2,5,8,11,14-Pentaaza[15]-16,29-phenanthrolinophane; / 12.38
524 / 1,14-Diphenyl-2,6,9,13-tetraazatetradecane; / 7.68
525 / 1,15-Diphenyl-2,5,8,11,14-pentaazapentadecane; / 13.63
526 / Tetraethylenepentamineheptaethanoic acid; / 18
527 / Diethylenetriamine-N,N',N"-triethanoic acid-N,N"-bis(butylamide); / 12.43
528 / N,N',N",N"'-Tetrakis(3-hydroxypropyl)-1,4,8,11-tetraazacyclotetradecane; / 6
529 / 4,7,13,16-Tetramethyl-1,4,7,10,13,16-hexaaza-21,24-dioxabicyclohexacosane; / 6.8
530 / 4-(2-Hydroxyethyl)-1,4,7,16,19,22-Hexaaza-10,13,25,28-tetraoxacyclotriacontane; / 9.55
531 / 1,4,19,22-Tetraoxa-7,10,13,16,25,28,31-Heptaazacyclotritriacontane; / 9.92
532 / N-[[(2-Aminoethyl)amino]ethyl]-N'-[2-[(anthracenylmethyl)amino]ethyl]-1,2-ethanediamine; / 11.73
533 / N-Acetyl-glycyl-histidinyl-valinyl-histidine ethyl ester; / 1.82
534 / 4,7,10,17,23-Pentamethyl-1,4,7,10,13,17,23-heptaazabicyclo[11.7.5]pentacosane; / 9.36
535 / N,N"-Bis(2-hydroxybenzyl)-2,5,8-triazanonane-N,N',N"-triethanoic acid; / 17.36
536 / 1,4-Bis(2,5,5-tris(carboxymethyl)-2,5-diazapentyl)benzene; / 15.93
537 / 7,16-Bis(2-pyridinylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane; / 6.96
538 / 4,7,13,16-Tetrakis(2-hydroxypropyl)-1,10-Dioxa-4,7,13,16-tetraazacyclooctadecane; / 6.26
539 / 7,19,30-Trioxa-1,4,10,13,16,22,27,33-octaazabicyclo[11.11.11]pentatriacontane; / 11.86
540 / 3,11-Bis(2-pyridylmethyl)-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene; / 14.65
541 / N-(9-Anthacenylmethyl)-3,6,9,12-tetraazatetradecane-1,14-diamine; / 12.84
542 / Desferrioxamine B; NH2.((CH2)5.NOH.CO.C2H4.CO.NH)2.(CH2)5.NOH.CO.CH3 / 10.56
543 / 3,12,20,29,35,36-Hexaaza-6,9,23,26-tetraoxatricyclo[29.3.1.1]-hexatriconta-hexaene; / 8.7
544 / 1-Hexadecyl-1,4,8,11-tetraazacyclotetradecane; / 11.1
545 / 1,5,9,12,16,20,24,27-Octaazatricyclo[18.10.2.2(5,16)]tetratriacontane; / 10.84
546 / 1,4,7,13-Tetramethyl-10,16-bis(2-pyridylmethyl)-1,4,7,10,13,16-hexaazacyclooctadecane; / 9.59
547 / 1,5,9,13,17,21,25,29-Octaazatricyclo[19.11.2.2(5,17)]hexatriacontane; / 8.5
548 / 1-(3,7,11,15-Tetramethyl)hexadecyl-1,4,8,11-tetraazacyclotetradecane; / 12.9
549 / 3,7,11-Tris(2-pyridylmethyl)-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene; / 11.92
550 / 2,2'-(7,10-DiMe-1-thia-4,7,10,13-tetraazacyclopentadeca-4,13-diyl)bis(methylene)bis-quinolinol; / 11.34
551 / 2,2'-(7,11-DiMe-1-thia-4,7,11,14-tetraazacyclohexadecan-4,14-diyl)bis(methylene)bis-quinolinol; / 11.34
552 / 2,2'-(7,11-DiMe-1-oxa-4,7,11,14-tetraazacyclohexadecan-4,14-diyl)bis(methylene)bis-8-quinolinol; / 10.41
553 / 6A-(2-Aminoethylamino)-6A-deoxy-beta-cyclodextrin; / 8.52
554 / 6A-[Bis(carboxymethyl)amino]-6A-deoxy-beta-cyclodextrin; / 6.08
555 / 6-((2-Bis(2-aminoethyl)amino)ethyl)amino)-6-deoxy-B-cyclodextrin; / 12.25
556 / 6A-(2-(2-(2-Aminoethylamino)ethylamino)ethylamino)-6A-deoxy-B-cyclodextrin; / 9.4

Table SM2. QSPR modeling of stability constants: The names of organic ligands (L) and experimental stability constant values (logK) for the equilibrium Cd2+ + L = (Cd2+)L in water at 298 K and an ionic strength 0.1 M.

no. / Ligand / logK
1 / Methylphosphonic acid; CH3.PO3H2 / 2.9
2 / Aminomethylphosphonic acid; H2N.CH2.PO3H2 / 5.14
3 / Ethanoic acid; CH3.COOH / 1.52
4 / 2-Aminoethanoic acid; H2N.CH2.COOH / 4.24
5 / 2-Aminoethanoic acid amide; H2N.CH2.CO.NH2 / 2.65
6 / 2-Mercaptoethanol; HS.CH2.CH2.OH / 6.11
7 / 2-Aminoethanol; H2N.CH2.CH2.OH / 2.77
8 / 3-Aminopropanoic acid; H2N.CH2.CH2.COOH / 2.88
9 / N-Methyl-2-aminoethanoic acid; CH3.NH.CH2.COOH / 3.61
10 / 1,2-Diaminoethane; H2N.CH2.CH2.NH2 / 5.4
11 / Imino-N,N-bis(methylenephosphonic acid); HN(CH2PO3H2)2 / 9.3
12 / 1,3-Diazole, imidazole; C3H4N2 / 2.67
13 / Propanedioic acid; CH2(COOH)2 / 2.59
14 / 2-Aminopropanoic acid; H2N.CH(CH3).COOH / 3.88
15 / 2-Amino-3-hydroxypropanoic acid; H2N.CH(CH2.OH)COOH / 4.07
16 / N-(Phosphonomethyl)glycine; H2O3P.CH2.NH.CH2.COOH / 7.29
17 / Sarcosine amide; CH3.NH.CH2.CO.NH2 / 2.19
18 / 1-Aminopropan-2-ol; H2N.CH2.CH(OH).CH3 / 3.54
19 / 3-Aminopropan-1-ol; HO.CH2.CH2.CH2.NH2 / 5.14
20 / Dimethylaminomethylphosphonic acid; (CH3)2N.CH2.PO3H2 / 5.17
21 / 1,3-Diaminopropane; H2N.CH2.CH2.CH2.NH2 / 4.5
22 / N-Methylimino-N,N-bis(methylenephosphonic acid); CH3.N(CH2PO3H2)2 / 10.15
23 / Ethylenediamine-N-methylenephosphonic acid; H2N.CH2.CH2.NH.CH2.PO3H2 / 8.2
24 / Propane-1,2,3-triamine; H2N.CH2.CH(NH2).CH2.NH2 / 5.99
25 / Nitrilotris(methylenephosphonic acid); N(CH2PO3H2)3 / 12.2
26 / 1,4-Butanedioic acid; HOOC.CH2.CH2.COOH / 2.03
27 / Methylpropanedioic acid; HOOC.CH(CH3).COOH / 2.58
28 / 2,2'-Thiodiglycolic acid, Thiodiethanoic acid; HOOC.CH2.S.CH2.COOH / 2.6
29 / 2-Mercaptosuccinic acid, 2-Sulfanyl-1,4-butanedioic acid; HOOC.CH(SH).CH2.COOH / 10.29
30 / 2-Hydroxybutane-1,4-dioic acid, Hydroxy-succinic acid; HOOC.CH2.CH(OH).COOH / 4.76
31 / Di(carboxy)methyl ether, 2,2'-Oxydiethanoic acid; HOOC.CH2.O.CH2.COOH / 3.21
32 / L-Tartaric acid, L-2,3-Dihydroxybutanedioic acid; HOOC.CH(OH).CH(OH).COOH / 2.83
33 / Aminobutanedioic acid; H2N.CH(CH2.COOH).COOH / 4.68
34 / Iminodiethanoic acid; HN(CH2.COOH)2 / 5.82
35 / 2-Aminobutanedioic acid 4-amide; H2N.CH(CH2.CO.NH2).COOH / 4.11
36 / Carboxymethyltartronic acid; / 4.49
37 / Pentane-2,4-dione; CH3.CO.CH2.CO.CH3 / 3.48
38 / Glycyl-glycine; H2N.CH2.CO.NH.CH2.COOH / 3.2
39 / 2-Aminobutanoic acid; CH3.CH2.CH(NH2).COOH / 3.46
40 / 4-Aminobutanoic acid; H2N.CH2.CH2.CH2.COOH / 3.36
41 / 2-Amino-3-methylmercaptopropanoic acid; H2N.CH(CH2.S.CH3)COOH / 3.77
42 / 2-Amino-3-hydroxybutanoic acid; H2N.CH(CH(OH).CH3)COOH / 4
43 / 2-Amino-4-hydroxybutanoic acid; HO.CH2.CH2.CH(NH2).COOH / 3.69
44 / Sarcosine methylamide; CH3.NH.CH2.CO.NH.CH3 / 2.14
45 / 2,2'-Iminodiethanol; HN(CH2.CH2.OH)2 / 2.4
46 / 2-Amino-2-(hydroxymethyl)-propan-1,3-diol; (HO.CH2)3C.NH2 / 1.94
47 / N-Carboxymethyl-N,N-bis(methylenephosphonic acid); HOOC.CH2.N(CH2.PO3H2)2 / 11.84