3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 103524
• Molecular Formular: C7H10O5
• Molecular Mass: 174.1513
• Monoisotopic Mass: 174.05282342
• SMILES: OC1CC(=CC(O)C1O)C(=O)O
• Canonical SMILES: OC1CC(=CC(C1O)O)C(=O)O
• InChI: InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)
• InChIKey: JXOHGGNKMLTUBP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: shikimate
• Synonyms: 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid; SHIKIMIC ACID

Database IDs

• CAS Number: 138-59-0
• EC Number: 205-334-2
• PubChem SID: 162090399
• PubChem CID: 1094

CALCULATED PROPERTIES

• Acid pKa: 4.103319
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.0506496
• LogD (pH = 7.4): -4.7369246
• Log P: -1.6400741
• Molar Refractivity: 38.9603 cm^3
• Polarizability: 15.229941 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 185-187°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: GW4600000

DETAILS

MP Biomedicals - 02152058

Crystalline
Intermediate useful for the biosynthesis of aromatic amino acids.