(2S)-2-amino-3-(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)propanoic acid

• ChemBase ID: 3936
• Molecular Formular: C9H9NO5
• Molecular Mass: 211.17146
• Monoisotopic Mass: 211.04807239
• SMILES: N[C@@H](CC1=CC(=O)C(=CC1=O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CC1=CC(=O)C(=CC1=O)O)N
• InChI: InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,13H,1,10H2,(H,14,15)/t5-/m0/s1
• InChIKey: AGMJSPIGDFKRRO-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)propanoic acid
• IUPAC Traditional name: topa quinone
• Synonyms: Topa quinone; 2,4,5-trihydroxyphenylalanine quinone; 5-(2-carboxy-2-aminoethyl)-2-hydroxy-1,4-benzoquinone; 5-(2-carboxy-2-aminoethyl)-4-hydroxy-1,2-benzoquinone; 6-hydroxydopa quinone

Database IDs

• PubChem SID: 160967371; 46505126
• PubChem CID: 123871

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7302854
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.7707329
• LogD (pH = 7.4): -2.8158488
• Log P: -2.7704587
• Molar Refractivity: 51.3704 cm^3
• Polarizability: 19.057798 Å^3
• Polar Surface Area: 117.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.02
• LOG S: -2.02
• Solubility (Water): 2.01e+00 g/l

DETAILS

DrugBank - DB04334

Drug information: experimental