{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(4-hydroxyphenyl)methyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 3692
• Molecular Formular: C28H42N7O17P3S
• Molecular Mass: 873.656063
• Monoisotopic Mass: 873.15707381
• SMILES: CC(C)(CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1OP(=O)(O)O)n1cnc2c1ncnc2N)[C@@H](O)C(=O)NCCC(=O)NCCSCc1ccc(O)cc1
• Canonical SMILES: O=C(NCCSCc1ccc(cc1)O)CCNC(=O)[C@@H](C(CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
• InChI: InChI=1S/C28H42N7O17P3S/c1-28(2,23(39)26(40)31-8-7-19(37)30-9-10-56-12-16-3-5-17(36)6-4-16)13-49-55(46,47)52-54(44,45)48-11-18-22(51-53(41,42)43)21(38)27(50-18)35-15-34-20-24(29)32-14-33-25(20)35/h3-6,14-15,18,21-23,27,36,38-39H,7-13H2,1-2H3,(H,30,37)(H,31,40)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t18-,21+,22-,23-,27+/m0/s1
• InChIKey: FZQUTWRNQJPTSH-URRMKJPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(4-hydroxyphenyl)methyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @4-hydroxybenzyl coenzyme A
• Synonyms: 4-Hydroxybenzyl Coenzyme A

Database IDs

• PubChem SID: 160967130; 46505458
• PubChem CID: 46936876

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 17
• H Donor: 10
• LogD (pH = 5.5): -8.636036
• LogD (pH = 7.4): -10.283468
• Log P: -5.1116796
• Molar Refractivity: 194.0339 cm^3
• Polarizability: 76.77238 Å^3
• Polar Surface Area: 366.79 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.28
• LOG S: -2.42
• Solubility (Water): 3.34e+00 g/l

DETAILS

DrugBank - DB04067

Drug information: experimental