(2S,3S)-2-amino-3-hydroxy-3-(indol-3-yl)propanoic acid

• ChemBase ID: 3778
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: N[C@@H]([C@@H](O)c1c[nH]c2ccccc12)C(=O)O
• Canonical SMILES: OC(=O)[C@H]([C@H](c1c[nH]c2c1cccc2)O)N
• InChI: InChI=1S/C11H12N2O3/c12-9(11(15)16)10(14)7-5-13-8-4-2-1-3-6(7)8/h1-5,9-10,13-14H,12H2,(H,15,16)/t9-,10-/m0/s1
• InChIKey: ITFHGBKXKUVKBW-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-amino-3-hydroxy-3-(indol-3-yl)propanoic acid
• IUPAC Traditional name: @β-hydroxytryptophane
• Synonyms: Beta-Hydroxytryptophane

Database IDs

• PubChem SID: 160967215; 46508787
• PubChem CID: 6857734

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9419171
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3427143
• LogD (pH = 7.4): -2.2921498
• Log P: -2.2832203
• Molar Refractivity: 55.9021 cm^3
• Polarizability: 23.391134 Å^3
• Polar Surface Area: 96.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.23
• LOG S: -1.37
• Solubility (Water): 9.39e+00 g/l

DETAILS

DrugBank - DB04159

Drug information: experimental