N-(3,4,6-Tri-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranosyl)-4-(4-{4-[bis(2-chloroethyl)amino]phenyl}butanamido)benzamide

ID: ALA500328

Chembl Id: CHEMBL500328

PubChem CID: 24984752

Max Phase: Preclinical

Molecular Formula: C33H40Cl2FN3O9

Molecular Weight: 712.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](NC(=O)c2ccc(NC(=O)CCCc3ccc(N(CCCl)CCCl)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C33H40Cl2FN3O9/c1-20(40)45-19-27-30(46-21(2)41)31(47-22(3)42)29(36)33(48-27)38-32(44)24-9-11-25(12-10-24)37-28(43)6-4-5-23-7-13-26(14-8-23)39(17-15-34)18-16-35/h7-14,27,29-31,33H,4-6,15-19H2,1-3H3,(H,37,43)(H,38,44)/t27-,29-,30-,31-,33-/m1/s1

Standard InChI Key:  XCVMYLVPWUDQGV-GJQHGMRUSA-N

Alternative Forms

1. Parent:

   

   ALA500328

   [(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-[[4-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]benzoyl]amino]-5-fluorooxan-2-yl]methyl acetate

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: 712.60

Molecular Weight (Monoisotopic): 711.2126

AlogP: 4.15

#Rotatable Bonds: 16

Polar Surface Area: 149.57

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.55

CX Basic pKa: 1.72

CX LogP: 4.25

CX LogD: 4.25

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.15

Np Likeness Score: -0.03

References

1. Reux B, Weber V, Galmier MJ, Borel M, Madesclaire M, Madelmont JC, Debiton E, Coudert P..  (2008)  Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives.,  16  (9): [PMID:18424156] [10.1016/j.bmc.2008.03.038]

2. El Hilali M, Reux B, Debiton E, Leal F, Galmier MJ, Vivier M, Chezal JM, Miot-Noirault E, Coudert P, Weber V..  (2017)  Linker structure-activity relationships in fluorodeoxyglucose chlorambucil conjugates for tumor-targeted chemotherapy.,  25  (20): [PMID:28927903] [10.1016/j.bmc.2017.08.043]

Source

Source(1):

• Scientific Literature