CAS 51411-04-2|2-{2,4-dioxo-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid|Alrestatin|alrestatine|alrestatin|(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid|2-{...

General Information

Structure

Molecular Formula

C₁₄H₉NO₄

Molecular Mass

255.22556

Exact Mass

255.05315777

Charge

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

Canonic Smiles

OC(=O)Cn1c(=O)c2cccc3c2c(c1=O)ccc3

Isomeric Smiles

c12c(=O)n(c(=O)c3c1c(ccc3)ccc2)CC(=O)O

Calculated Properties

JChem

Acid pKa

3.4518325

H Acceptors

H Donor

LogD (pH = 5.5)

-0.6533717

LogD (pH = 7.4)

-2.0046601

Log P

1.3845592

Molar Refractivity

66.7463

Polarizability

25.844305

Polar Surface Area

74.68

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.95

LOG S

-3.62

Solubility (Water)

6.14e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

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[7.3.1.0⁵,¹³]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 acidAlrestatin

IUPAC Traditional name

alrestatine alrestatin 2-{2,4-dioxo-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid

Names and Identifiers

Registration numbers

PubChem CID

PubChem SID

CAS Number

MDL Number

Registration numbers

Properties

Physical Property

Partition Coefficient

1.796

Product Information

Purity

95+%

Application(s)

Aldose reductase inhibitor investigated for treatment of diabetic polyneuropathy

Pharmacology Properties

Mechanism of Action

Aldose reductase inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB02020

Drug information: experimental

Molecule Details

References

PubChem Literature

From Data Sources

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 277

• Humber, L.G., Prog. Med. Chem., 1987, 24, 299, (rev)

• Gabbay, K.H. et al., Metab., Clin. Exp., (Suppl. 1), 1979, 28, 471, (metab)

• U.S. Pat., 1974, Ayerst McKenna and Harrison, 3 821 383; CA, 81, 176158, (synth, pharmacol)

• El-Naggar, A.M. et al., Egypt. J. Chem., 1981, 24, 127, (synth)

• Varma, S.D. et al., Science (Washington, D.C.), 1975, 188, 1215, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• IUPAC name

• Synonyms

• IUPAC Traditional name

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

• MDL Number

Properties

• Physical Property

• Product Information

• Pharmacology Properties

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Molecule

ID:1786