2-{4-[(2R)-2-{[(1S)-1-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl]carbamoyl}-2-acetamidoethyl]-2-phosphonophenoxy}acetic acid

• ChemBase ID: 3633
• Molecular Formular: C29H38N3O10P
• Molecular Mass: 619.599881
• Monoisotopic Mass: 619.22948106
• SMILES: C[C@H](NC(=O)[C@@H](Cc1ccc(OCC(=O)O)c(c1)P(=O)(O)O)NC(=O)C)c1ccc(OCC2CCCCC2)c(c1)C(=O)N
• Canonical SMILES: CC(=O)N[C@@H](C(=O)N[C@H](c1ccc(c(c1)C(=O)N)OCC1CCCCC1)C)Cc1ccc(c(c1)P(=O)(O)O)OCC(=O)O
• InChI: InChI=1S/C29H38N3O10P/c1-17(21-9-11-24(22(14-21)28(30)36)41-15-19-6-4-3-5-7-19)31-29(37)23(32-18(2)33)12-20-8-10-25(42-16-27(34)35)26(13-20)43(38,39)40/h8-11,13-14,17,19,23H,3-7,12,15-16H2,1-2H3,(H2,30,36)(H,31,37)(H,32,33)(H,34,35)(H2,38,39,40)/t17-,23+/m0/s1
• InChIKey: FXUGQWABROMTDA-GAJHUEQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2R)-2-{[(1S)-1-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl]carbamoyl}-2-acetamidoethyl]-2-phosphonophenoxy}acetic acid
• IUPAC Traditional name: 4-[(2R)-2-{[(1S)-1-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl]carbamoyl}-2-acetamidoethyl]-2-phosphonophenoxyacetic acid
• Synonyms: (4-{2-Acetylamino-2-[1-(3-Carbamoyl-4-Cyclohexylmethoxy-Phenyl)-Ethylcarbamoyl}-Ethyl}-2-Phosphono-Phenoxy)-Acetic Acid

Database IDs

• PubChem SID: 160967071; 46509016
• PubChem CID: 46936859

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.602613
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.6857889
• LogD (pH = 7.4): -5.7127924
• Log P: 0.5684
• Molar Refractivity: 155.3332 cm^3
• Polarizability: 60.11572 Å^3
• Polar Surface Area: 214.58 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.63
• LOG S: -5.63
• Solubility (Water): 1.45e-03 g/l

DETAILS

DrugBank - DB04003

Drug information: experimental