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

ID: ALA501118

Chembl Id: CHEMBL501118

PubChem CID: 24984753

Max Phase: Preclinical

Molecular Formula: C28H38Cl2FN3O9

Molecular Weight: 650.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](NC(=O)CNC(=O)CCCc2ccc(N(CCCl)CCCl)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C28H38Cl2FN3O9/c1-17(35)40-16-22-26(41-18(2)36)27(42-19(3)37)25(31)28(43-22)33-24(39)15-32-23(38)6-4-5-20-7-9-21(10-8-20)34(13-11-29)14-12-30/h7-10,22,25-28H,4-6,11-16H2,1-3H3,(H,32,38)(H,33,39)/t22-,25-,26-,27-,28-/m1/s1

Standard InChI Key:  DARVQDNECNKPHC-DVVXUNHVSA-N

Alternative Forms

1. Parent:

   

   ALA501118

   n-[2-(3,4,6-Tri-o-acetyl-2-deoxy-2-fluoro-beta-d-glucopyranosylamino)-2-oxoethyl]-4-{4-[bis(2-chloroethyl)amino]phenyl}butanamide

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: 650.53

Molecular Weight (Monoisotopic): 649.1969

AlogP: 2.02

#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: 11.48

CX Basic pKa: 1.72

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.15

Np Likeness Score: 0.17

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