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

• ChemBase ID: 1616
• Molecular Formular: C21H36N7O17P3S
• Molecular Mass: 783.533523
• Monoisotopic Mass: 783.11012362
• 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)NCCSO
• Canonical SMILES: OSCCNC(=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/C21H36N7O17P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-49-40)8-42-48(38,39)45-47(36,37)41-7-11-15(44-46(33,34)35)14(30)20(43-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,40H,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: HWMGJMKHOJKGLQ-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-3-[(2-{[2-(hydroxysulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @oxidized coenzyme A
• Synonyms: Oxidized Coenzyme A

Database IDs

• PubChem SID: 46506694; 160965073
• PubChem CID: 46936236

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 17
• H Donor: 10
• LogD (pH = 5.5): -10.720015
• LogD (pH = 7.4): -12.364035
• Log P: -7.1957026
• Molar Refractivity: 164.5171 cm^3
• Polarizability: 65.64897 Å^3
• Polar Surface Area: 366.79 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.87
• LOG S: -2.2
• Solubility (Water): 4.91e+00 g/l

DETAILS

DrugBank - DB01846

Drug information: experimental