5,6-dihydroxy-1H-indole-2-carboxylic acid

• ChemBase ID: 167818
• Molecular Formular: C9H7NO4
• Molecular Mass: 193.15618
• Monoisotopic Mass: 193.03750771
• SMILES: c1(c(cc2c(c1)[nH]c(c2)C(=O)O)O)O
• Canonical SMILES: Oc1cc2[nH]c(cc2cc1O)C(=O)O
• InChI: InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
• InChIKey: YFTGOBNOJKXZJC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,6-dihydroxy-1H-indole-2-carboxylic acid
• IUPAC Traditional name: dhica
• Synonyms: 2-Carboxy-5,6-dihydroxyindole; 5,6-Dihydroxy-1H-indole-2-carboxylic Acid; 5,6-Dihydroxy-2-carboxyindole; 5,6-Dihydroxyindole-2-carboxylic Acid

Database IDs

• CAS Number: 4790-08-3
• PubChem SID: 162261951
• PubChem CID: 119405

CALCULATED PROPERTIES

• Acid pKa: 3.6035254
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.84974855
• LogD (pH = 7.4): -2.3192332
• Log P: 1.0424612
• Molar Refractivity: 48.24 cm^3
• Polarizability: 19.099907 Å^3
• Polar Surface Area: 93.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Beige to Pale Yellow Solid
• Melting Point: 211-214°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D452825

5,6-Dihydroxyindole-2-carboxylic Acid is the indole analogue of DOPA. 5,6-Dihydroxyindole-2-carboxylic Acid is a precursor to melanin as well as potential as HIV-1 integrase inhibitors.

REFERENCES

• Hansson, C.: Acta Derm.-Venereol., 63, 147 (1983)
• Sechi, M. et al.: Antiviral Chem. Chemother., 15, 67 (1983)