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

• ChemBase ID: 3272
• Molecular Formular: C29H42N7O18P3S
• Molecular Mass: 901.666163
• Monoisotopic Mass: 901.15198843
• 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)NCCSCC(=O)c1ccc(O)cc1
• Canonical SMILES: O=C(NCCSCC(=O)c1ccc(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/C29H42N7O18P3S/c1-29(2,24(41)27(42)32-8-7-20(39)31-9-10-58-12-18(38)16-3-5-17(37)6-4-16)13-51-57(48,49)54-56(46,47)50-11-19-23(53-55(43,44)45)22(40)28(52-19)36-15-35-21-25(30)33-14-34-26(21)36/h3-6,14-15,19,22-24,28,37,40-41H,7-13H2,1-2H3,(H,31,39)(H,32,42)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t19-,22+,23-,24-,28+/m0/s1
• InChIKey: ZQLMPRRTUJBILA-LDPGJOAVSA-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-{[2-(4-hydroxyphenyl)-2-oxoethyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @4-hydroxyphenacyl coenzyme A
• Synonyms: 4-Hydroxyphenacyl Coenzyme A

Database IDs

• PubChem SID: 160966714; 46506287
• PubChem CID: 46936729

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.81367934
• H Acceptors: 18
• H Donor: 10
• LogD (pH = 5.5): -9.338248
• LogD (pH = 7.4): -11.14057
• Log P: -5.8114867
• Molar Refractivity: 199.4214 cm^3
• Polarizability: 78.738945 Å^3
• Polar Surface Area: 383.86 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.06
• LOG S: -2.44
• Solubility (Water): 3.26e+00 g/l

DETAILS

DrugBank - DB03613

Drug information: experimental