(2S)-2-amino-4-{[(1R)-2-({2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ5-oxazaphosphinan-4-yl}sulfanyl)-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 169718
• Molecular Formular: C17H30Cl2N5O8PS
• Molecular Mass: 566.393561
• Monoisotopic Mass: 565.09297594
• SMILES: O1CCC(NP1(=O)N(CCCl)CCCl)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H](N)C(=O)O
• Canonical SMILES: ClCCN(P1(=O)OCCC(N1)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)CCCl
• InChI: InChI=1S/C17H30Cl2N5O8PS/c18-4-6-24(7-5-19)33(31)23-14(3-8-32-33)34-10-12(16(28)21-9-15(26)27)22-13(25)2-1-11(20)17(29)30/h11-12,14H,1-10,20H2,(H,21,28)(H,22,25)(H,23,31)(H,26,27)(H,29,30)/t11-,12-,14?,33?/m0/s1
• InChIKey: CXEDBYAXQXFDHD-XNZWOTSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-({2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ^5-oxazaphosphinan-4-yl}sulfanyl)-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-2-({2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ^5-oxazaphosphinan-4-yl}sulfanyl)-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-S-[2-[bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl]-L-cysteinylglycine; N-[S-[2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl]-N-L-γ-glutamyl-L-cysteinyl]glycine; 4-Glutathionyl Cyclophosphamide

Database IDs

• CAS Number: 77273-67-7
• PubChem SID: 162263850
• PubChem CID: 71317120

CALCULATED PROPERTIES

• Acid pKa: 1.8055136
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.964343
• LogD (pH = 7.4): -7.5623612
• Log P: -4.40174
• Molar Refractivity: 124.84 cm^3
• Polarizability: 50.154522 Å^3
• Polar Surface Area: 200.39 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G597980

4-Glutathionyl Cyclophosphamide is the gluthione conjugated metabolite of the chemotherapeutic agent, Cyclophosphamide (C988580).

REFERENCES

• Dirven, H.A. et al.: Cancer Res., 54, 6215 (1994)
• Li, F. et al.: Biochem. Pharmacol., 90, 1063 (1994)