2-{2,4-dioxo-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid

• ChemBase ID: 1786
• Molecular Formular: C14H9NO4
• Molecular Mass: 255.22556
• Monoisotopic Mass: 255.05315777
• SMILES: c12c(=O)n(c(=O)c3c1c(ccc3)ccc2)CC(=O)O
• Canonical SMILES: OC(=O)Cn1c(=O)c2cccc3c2c(c1=O)ccc3
• InChI: InChI=1S/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)
• InChIKey: GCUCIFQCGJIRNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2,4-dioxo-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid; 2-{2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid
• IUPAC Traditional name: alrestatine; alrestatin; 2-{2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid
• Synonyms: Alrestatin; (1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid; Alrestatin

Database IDs

• CAS Number: 51411-04-2
• MDL Number: MFCD00181399
• PubChem SID: 160965242; 46508635
• PubChem CID: 2120

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4518325
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.6533717
• LogD (pH = 7.4): -2.0046601
• Log P: 1.3845592
• Molar Refractivity: 66.7463 cm^3
• Polarizability: 25.844305 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.95
• LOG S: -3.62
• Solubility (Water): 6.14e-02 g/l

PROPERTIES

Physical Property

• Partition Coefficient: 1.796

Pharmacology Properties

• Mechanism of Action: Aldose reductase inhibitor

Product Information

• Purity: 95+%
• Application(s): Aldose reductase inhibitor investigated for treatment of diabetic polyneuropathy

DETAILS

DrugBank - DB02020

Drug information: experimental

REFERENCES

• U.S. Pat., 1974, Ayerst McKenna and Harrison, 3 821 383; CA, 81, 176158, (synth, pharmacol)
• Varma, S.D. et al., Science (Washington, D.C.), 1975, 188, 1215, (pharmacol)
• Gabbay, K.H. et al., Metab., Clin. Exp., (Suppl. 1), 1979, 28, 471, (metab)
• El-Naggar, A.M. et al., Egypt. J. Chem., 1981, 24, 127, (synth)
• Humber, L.G., Prog. Med. Chem., 1987, 24, 299, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 277