2-amino-4-[(2-{[2-(4-azidophenyl)-2-oxoethyl]sulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid

• ChemBase ID: 132058
• Molecular Formular: C18H22N6O7S
• Molecular Mass: 466.46828
• Monoisotopic Mass: 466.12706807
• SMILES: c1cc(ccc1C(=O)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=Nc1ccc(cc1)C(=O)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• InChI: InChI=1S/C18H22N6O7S/c19-12(18(30)31)5-6-15(26)22-13(17(29)21-7-16(27)28)8-32-9-14(25)10-1-3-11(4-2-10)23-24-20/h1-4,12-13H,5-9,19H2,(H,21,29)(H,22,26)(H,27,28)(H,30,31)
• InChIKey: POHHFIIXXRDDJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-[(2-{[2-(4-azidophenyl)-2-oxoethyl]sulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
• IUPAC Traditional name: 2-amino-4-[(2-{[2-(4-azidophenyl)-2-oxoethyl]sulfanyl}-1-(carboxymethylcarbamoyl)ethyl)carbamoyl]butanoic acid
• Synonyms: S-(p-Azidophenacyl)glutathione

Database IDs

• CAS Number: 73322-71-1
• MDL Number: MFCD00056740
• PubChem SID: 162226335
• PubChem CID: 5131

CALCULATED PROPERTIES

• Acid pKa: 1.8028347
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -5.1284933
• LogD (pH = 7.4): -6.541969
• Log P: -3.939683
• Molar Refractivity: 114.1028 cm^3
• Polarizability: 43.030148 Å^3
• Polar Surface Area: 205.32 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - A1782

Biochem/physiol Actions
Photoaffinity derivative of glutathione. Reported to inhibit glyoxalase and glutathione S-transferase.