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

• ChemBase ID: 153140
• Molecular Formular: C7H11O8P
• Molecular Mass: 254.131201
• Monoisotopic Mass: 254.01915394
• SMILES: C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)OP(=O)(O)O)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+/m1/s1
• InChIKey: QYOJSKGCWNAKGW-PBXRRBTRSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD04039676
• PubChem SID: 162247280
• PubChem CID: 121947

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C7H11O8P

DETAILS

Sigma Aldrich - S8570

Biochem/physiol Actions
Substrate for EPSP synthase