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

• ChemBase ID: 1759
• Molecular Formular: C21H36N7O16P3S
• Molecular Mass: 767.534123
• Monoisotopic Mass: 767.115209
• 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)NCCS
• Canonical SMILES: SCCNC(=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/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14+,15-,16-,20+/m0/s1
• InChIKey: RGJOEKWQDUBAIZ-VPHNIEJBSA-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-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @coenzyme A
• Synonyms: Coenzyme A

Database IDs

• CAS Number: 85-61-0
• PubChem SID: 160965215; 46507023
• PubChem CID: 46936280

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 16
• H Donor: 10
• LogD (pH = 5.5): -10.340141
• LogD (pH = 7.4): -11.985006
• Log P: -6.8158183
• Molar Refractivity: 162.7402 cm^3
• Polarizability: 64.9052 Å^3
• Polar Surface Area: 346.56 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.61
• LOG S: -2.22
• Solubility (Water): 4.64e+00 g/l

DETAILS

DrugBank - DB01992

• Drug Groups: experimental
• External Links: Wikipedia