1H-pyrrole-2,3,5-tricarboxylic acid

• ChemBase ID: 177227
• Molecular Formular: C7H5NO6
• Molecular Mass: 199.1177
• Monoisotopic Mass: 199.01168689
• SMILES: c1(cc([nH]c1C(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)c1cc(c([nH]1)C(=O)O)C(=O)O
• InChI: InChI=1S/C7H5NO6/c9-5(10)2-1-3(6(11)12)8-4(2)7(13)14/h1,8H,(H,9,10)(H,11,12)(H,13,14)
• InChIKey: UGSAVTSXHXRENH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-pyrrole-2,3,5-tricarboxylic acid
• IUPAC Traditional name: 1H-pyrrole-2,3,5-tricarboxylic acid
• Synonyms: 1H-Pyrrole-2,3,5-tricarboxylic Acid Acetic Acid Salt; PTCA; Pyrrole-2,3,5-tricarboxylic Acid Acetic Acid Salt

Database IDs

• PubChem SID: 164233137
• PubChem CID: 150868

CALCULATED PROPERTIES

• Acid pKa: 3.2045636
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.8453295
• LogD (pH = 7.4): -7.5905385
• Log P: -0.1341191
• Molar Refractivity: 42.3404 cm^3
• Polarizability: 15.461112 Å^3
• Polar Surface Area: 127.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P997885

The most characteristic degrdadation product of melanins. An important biomarker for Melatonin (M215000) metabolism.

REFERENCES

• Shen, X., et al.: J. Med. Chem., 39, 2018 (1996)
• Xin, W., et a: Chem. Res. Toxicol., 13, 749 (1996)
• An, L., et al.: Food Chem. Toxicol., 44, 436 (1996)