2-[(Z)-(formylimino)amino]pentanedioic acid

• ChemBase ID: 169455
• Molecular Formular: C6H8N2O5
• Molecular Mass: 188.13812
• Monoisotopic Mass: 188.04332137
• SMILES: C(CC(/N=N\C=O)C(=O)O)C(=O)O
• Canonical SMILES: O=C/N=N\C(C(=O)O)CCC(=O)O
• InChI: InChI=1S/C6H8N2O5/c9-3-7-8-4(6(12)13)1-2-5(10)11/h3-4H,1-2H2,(H,10,11)(H,12,13)/b8-7-
• InChIKey: ZMMIQVLVCFMWDD-FPLPWBNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(Z)-(formylimino)amino]pentanedioic acid
• IUPAC Traditional name: 2-[(Z)-(formylimino)amino]pentanedioic acid
• Synonyms: (R,S)-2-(Formylazo)pentanedioic Acid; D,L-2-(Formylazo)glutaric Acid; 2-(2-Formylhydrazinylidene)pentanedioic Acid; rac N-Formiminoglutamic Acid

Database IDs

• CAS Number: 943418-43-7
• PubChem SID: 162263587
• PubChem CID: 71316978

CALCULATED PROPERTIES

• Acid pKa: 3.083094
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -4.8386345
• LogD (pH = 7.4): -7.552863
• Log P: -0.84682953
• Molar Refractivity: 38.141 cm^3
• Polarizability: 14.968266 Å^3
• Polar Surface Area: 116.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F735500

A histidine metabolite; the regulation of folate and methionine metabolism.

REFERENCES

• Krebs, H.A., et al.: Biochem. J., 158, 341 (1976)