(1S,3S,4S,5R)-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

• ChemBase ID: 2320
• Molecular Formular: C8H15O8P
• Molecular Mass: 270.173661
• Monoisotopic Mass: 270.05045407
• SMILES: O[C@H]1C[C@@](O)(C[C@@H](CP(=O)(O)O)[C@@H]1O)C(=O)O
• Canonical SMILES: O[C@H]1[C@H](CP(=O)(O)O)C[C@@](C[C@@H]1O)(O)C(=O)O
• InChI: InChI=1S/C8H15O8P/c9-5-2-8(13,7(11)12)1-4(6(5)10)3-17(14,15)16/h4-6,9-10,13H,1-3H2,(H,11,12)(H2,14,15,16)/t4-,5-,6-,8-/m0/s1
• InChIKey: BKLICLLAHMTUPK-TYQACLPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,4S,5R)-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid
• IUPAC Traditional name: @carbaphosphonate
• Synonyms: Carbaphosphonate

Database IDs

• PubChem SID: 46505074; 160965772
• PubChem CID: 46936432

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7972234
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -7.459197
• LogD (pH = 7.4): -9.051245
• Log P: -3.3548493
• Molar Refractivity: 53.7293 cm^3
• Polarizability: 21.814016 Å^3
• Polar Surface Area: 155.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.73
• LOG S: -0.81
• Solubility (Water): 4.21e+01 g/l

DETAILS

DrugBank - DB02592

Drug information: experimental