(3S,4R,5S)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 3930
• Molecular Formular: C7H11O8P
• Molecular Mass: 254.131201
• Monoisotopic Mass: 254.01915394
• SMILES: O[C@H]1CC(=C[C@H](OP(=O)(O)O)[C@@H]1O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@@H](O)CC(=C[C@@H]1OP(=O)(O)O)C(=O)O
• InChI: InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m0/s1
• InChIKey: QYOJSKGCWNAKGW-HCWXCVPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5S)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: @shikimate-3-phosphate
• Synonyms: Shikimate-3-Phosphate

Database IDs

• PubChem SID: 46504914; 160967365
• PubChem CID: 46936949

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3157644
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.590323
• LogD (pH = 7.4): -8.215488
• Log P: -1.7636402
• Molar Refractivity: 49.8332 cm^3
• Polarizability: 19.837679 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.07
• LOG S: -1.08
• Solubility (Water): 2.10e+01 g/l

DETAILS

DrugBank - DB04328

Drug information: experimental