methyl (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate

• ChemBase ID: 174218
• Molecular Formular: C8H12O5
• Molecular Mass: 188.17788
• Monoisotopic Mass: 188.06847348
• SMILES: C1(=C[C@H]([C@H]([C@@H](C1)O)O)O)C(=O)OC
• Canonical SMILES: COC(=O)C1=C[C@H]([C@H]([C@@H](C1)O)O)O
• InChI: InChI=1S/C8H12O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2,5-7,9-11H,3H2,1H3/t5-,6-,7-/m1/s1
• InChIKey: LSNUUAUXWJZSFD-FSDSQADBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: methyl (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
• Synonyms: (3R,4S,5R)-1-Cyclohexene-1-carboxylic Acid, 3,4,5-Trihydroxy-methyl Ester; Shikimic Acid Methyl Ester; Methyl Shikimate; NSC 280656; Methyl (-)-Shikimate

Database IDs

• CAS Number: 40983-58-2
• PubChem SID: 164230128
• PubChem CID: 10773951

CALCULATED PROPERTIES

• Acid pKa: 13.004749
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.2608467
• LogD (pH = 7.4): -1.2608478
• Log P: -1.2608467
• Molar Refractivity: 43.7294 cm^3
• Polarizability: 17.26901 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 114-115°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M325980

A common biosynthetic precursor

REFERENCES

• Fiorini, M., et al.: Biophys. J., 80, 2471 (2001)
• Li, C., et al.: Bioorg. Med. Chem. Lett., 17, 6687 (2001)
• Wang, R., et al.: J. Ethnopharmacol., 117, 249 (2001)