{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3S)-3-({2-[(2-{[(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 3739
• Molecular Formular: C32H47N8O17P3S
• Molecular Mass: 940.745263
• Monoisotopic Mass: 940.19927297
• SMILES: CN(C)c1ccc(cc1)/C=C/C(=O)SCCNC(=O)CCNC(=O)[C@@H](O)C(C)(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
• Canonical SMILES: O=C(NCCSC(=O)/C=C/c1ccc(cc1)N(C)C)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/C32H47N8O17P3S/c1-32(2,27(44)30(45)35-12-11-22(41)34-13-14-61-23(42)10-7-19-5-8-20(9-6-19)39(3)4)16-54-60(51,52)57-59(49,50)53-15-21-26(56-58(46,47)48)25(43)31(55-21)40-18-38-24-28(33)36-17-37-29(24)40/h5-10,17-18,21,25-27,31,43-44H,11-16H2,1-4H3,(H,34,41)(H,35,45)(H,49,50)(H,51,52)(H2,33,36,37)(H2,46,47,48)/b10-7+/t21-,25+,26-,27+,31+/m0/s1
• InChIKey: WWUPGKDRUIPTRA-OBPDMEEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3S)-3-({2-[(2-{[(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3S)-3-({2-[(2-{[(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: 4-(N,N-Dimethylamino)Cinnamoyl-Coa

Database IDs

• PubChem SID: 46505326; 160967177
• PubChem CID: 46936893

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136253
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -7.281757
• LogD (pH = 7.4): -9.424716
• Log P: -5.488917
• Molar Refractivity: 217.0528 cm^3
• Polarizability: 84.51713 Å^3
• Polar Surface Area: 366.87 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.37
• LOG S: -2.56
• Solubility (Water): 2.59e+00 g/l

DETAILS

DrugBank - DB04117

Drug information: experimental