(2S)-2-amino-4-{[(1R)-2-[(2-{[amino(hydroxy)phosphoryl](2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}ethyl)amino}ethyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 167461
• Molecular Formular: C24H43N8O14PS2
• Molecular Mass: 762.747181
• Monoisotopic Mass: 762.20777673
• SMILES: N(CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H](N)C(=O)O)(CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H](N)C(=O)O)P(=O)(N)O
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSCCN(P(=O)(O)N)CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C24H43N8O14PS2/c25-13(23(41)42)1-3-17(33)30-15(21(39)28-9-19(35)36)11-48-7-5-32(47(27,45)46)6-8-49-12-16(22(40)29-10-20(37)38)31-18(34)4-2-14(26)24(43)44/h13-16H,1-12,25-26H2,(H,28,39)(H,29,40)(H,30,33)(H,31,34)(H,35,36)(H,37,38)(H,41,42)(H,43,44)(H3,27,45,46)/t13-,14-,15-,16-/m0/s1
• InChIKey: UVGSFFNNXIWBSA-VGWMRTNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-[(2-{[amino(hydroxy)phosphoryl](2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}ethyl)amino}ethyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-2-[(2-{[amino(hydroxy)phosphoryl](2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}ethyl)amino}ethyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
• Synonyms: 2,2'-[[(aminohydroxyphosphinyl)imino]di-2,1-ethanediyl]bis[L-γ-glutamyl-L-cysteinylglycine]; Diglutathionyl Mustard Phosphoramide

Database IDs

• CAS Number: 145784-68-5
• PubChem SID: 162261594
• PubChem CID: 71316088

CALCULATED PROPERTIES

• Acid pKa: 1.5099235
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -15.170538
• LogD (pH = 7.4): -19.774246
• Log P: -11.55124
• Molar Refractivity: 171.5163 cm^3
• Polarizability: 68.10933 Å^3
• Polar Surface Area: 384.2 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D446250

Diglutathionyl Mustard Phosphoramide is the diglutathionyl conjugate of phosphoramide mustard (PM), a cytotoxic metabolite of Cyclophosphamide (C988580).

REFERENCES

• Driven, H.A.A.M. et al.: Chem. BIol. Inter., 93, 185 (1994)
• Fenselau, C. et al.: Xenobiotica, 22, 1207 (1994)