Phosphamide mustard conjugate

ID: ALA3706541

Cas Number: 145784-68-5

PubChem CID: 71316088

Max Phase: Preclinical

Molecular Formula: C24H43N8O14PS2

Molecular Weight: 762.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSCCN(CCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)P(N)(=O)O)C(=O)NCC(=O)O)C(=O)O

Standard 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

Standard InChI Key:  UVGSFFNNXIWBSA-VGWMRTNUSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3706541

   Diglutathionyl Mustard Phosphoramide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 762.76

Molecular Weight (Monoisotopic): 762.2078

AlogP: -4.43

#Rotatable Bonds: 27

Polar Surface Area: 384.20

Molecular Species: ZWITTERION

HBA: 13

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 15

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.51

CX Basic pKa: 9.61

CX LogP: -11.55

CX LogD: -19.77

Aromatic Rings: ┄

Heavy Atoms: 49

QED Weighted: 0.03

Np Likeness Score: 0.13

References

1. Zhong S, Huang M, Yang X, Liang L, Wang Y, Romkes M, Duan W, Chan E, Zhou SF..  (2006)  Relationship of glutathione S-transferase genotypes with side-effects of pulsed cyclophosphamide therapy in patients with systemic lupus erythematosus.,  62  (4): [PMID:16995867] [10.1111/j.1365-2125.2006.02690.x]

Source

Source(1):

• Curated Drug Metabolism Pathways