(1S,4R,5R)-3,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

• ChemBase ID: 3946
• Molecular Formular: C7H10O5
• Molecular Mass: 174.1513
• Monoisotopic Mass: 174.05282342
• SMILES: O[C@@H]1C[C@@H](C=C(O)[C@@H]1O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1C[C@@H](O)[C@H](C(=C1)O)O
• InChI: InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,3,5-6,8-10H,2H2,(H,11,12)/t3-,5-,6+/m1/s1
• InChIKey: YVYKOQWMJZXRRM-PUFIMZNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,5R)-3,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
• IUPAC Traditional name: @3-dehydroshikimate
• Synonyms: 3-Dehydroshikimate

Database IDs

• PubChem SID: 46507545; 160967381
• PubChem CID: 46936953

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.9420965
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.0196912
• LogD (pH = 7.4): -4.9773726
• Log P: -1.4483267
• Molar Refractivity: 39.7318 cm^3
• Polarizability: 15.229941 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.47
• LOG S: 0.02
• Solubility (Water): 1.84e+02 g/l

DETAILS

DrugBank - DB04347

Drug information: experimental