4-{5-[bis(2-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}ethyl)amino]-1-methyl-1H-1,3-benzodiazol-2-yl}butanoic acid

• ChemBase ID: 161181
• Molecular Formular: C26H37N5O8S2
• Molecular Mass: 611.73068
• Monoisotopic Mass: 611.20835517
• SMILES: c1(ccc2c(c1)nc(n2C)CCCC(=O)O)N(CCSC[C@H](NC(=O)C)C(=O)O)CCSC[C@H](NC(=O)C)C(=O)O
• Canonical SMILES: OC(=O)CCCc1nc2c(n1C)ccc(c2)N(CCSC[C@@H](C(=O)O)NC(=O)C)CCSC[C@@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C26H37N5O8S2/c1-16(32)27-20(25(36)37)14-40-11-9-31(10-12-41-15-21(26(38)39)28-17(2)33)18-7-8-22-19(13-18)29-23(30(22)3)5-4-6-24(34)35/h7-8,13,20-21H,4-6,9-12,14-15H2,1-3H3,(H,27,32)(H,28,33)(H,34,35)(H,36,37)(H,38,39)/t20-,21-/m0/s1
• InChIKey: YSTNDPUOARKGRL-SFTDATJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{5-[bis(2-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}ethyl)amino]-1-methyl-1H-1,3-benzodiazol-2-yl}butanoic acid
• IUPAC Traditional name: 4-{5-[bis(2-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}ethyl)amino]-1-methyl-1,3-benzodiazol-2-yl}butanoic acid
• Synonyms: 5-[Bis[2-[[(2R)-2-(acetylamino)-2-carboxyethyl]thio]ethyl]amino]-1-methyl-1H-benzimidazole-2-butanoic Acid; Bendamustine Bis-mercapturic Acid

Database IDs

• CAS Number: 956344-34-6
• PubChem SID: 162255316
• PubChem CID: 46780657

CALCULATED PROPERTIES

• Acid pKa: 3.5075643
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.6313062
• LogD (pH = 7.4): -7.892883
• Log P: -1.3930701
• Molar Refractivity: 155.334 cm^3
• Polarizability: 60.90077 Å^3
• Polar Surface Area: 191.16 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B132480

Metabolite of Bendamustine

REFERENCES

• Hinchman, C., et al.: J. Biol. Chem., 266, 22179 (1991)
• Hinchman, C., et al.: J. Toxicol. Env. Health, 41, 387 (1991)
• Teichert, J., et al.: Drug Metab. Dispos., 33, 984 (1991)