(3R,4S,5R)-5-amino-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 125802
• Molecular Formular: C7H11NO4
• Molecular Mass: 173.16654
• Monoisotopic Mass: 173.06880784
• SMILES: O=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](N)C1
• Canonical SMILES: O[C@H]1[C@H](N)CC(=C[C@H]1O)C(=O)O
• InChI: InChI=1S/C7H11NO4/c8-4-1-3(7(11)12)2-5(9)6(4)10/h2,4-6,9-10H,1,8H2,(H,11,12)/t4-,5-,6+/m1/s1
• InChIKey: GSAKPGCLECHWSP-PBXRRBTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R)-5-amino-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: aminoshikimic acid
• Synonyms: Aminoshikimate; Aminoshikimic acid

Database IDs

• CAS Number: 178948-66-8
• PubChem SID: 162220149
• PubChem CID: 443636
• Chemspider ID: 391778
• Wikipedia Title: Aminoshikimic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.9970767
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.020415
• LogD (pH = 7.4): -4.013032
• Log P: -4.011057
• Molar Refractivity: 40.6178 cm^3
• Polarizability: 16.05288 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true