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

ID: ALA447306

Chembl Id: CHEMBL447306

PubChem CID: 24984755

Max Phase: Preclinical

Molecular Formula: C34H42Cl2FN3O10

Molecular Weight: 742.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2ccc(NC(=O)CNC(=O)CCCc3ccc(N(CCCl)CCCl)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C34H42Cl2FN3O10/c1-21(41)46-20-28-32(47-22(2)42)33(48-23(3)43)31(37)34(50-28)49-27-13-9-25(10-14-27)39-30(45)19-38-29(44)6-4-5-24-7-11-26(12-8-24)40(17-15-35)18-16-36/h7-14,28,31-34H,4-6,15-20H2,1-3H3,(H,38,44)(H,39,45)/t28-,31-,32-,33-,34-/m1/s1

Standard InChI Key:  LVEKWDFTSRIFMY-BNNJPYFFSA-N

Alternative Forms

1. Parent:

   

   ALA447306

   N-{2-[4-(3,4,6-Tri-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranosyloxy)phenyl]amino-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: 742.63

Molecular Weight (Monoisotopic): 741.2231

AlogP: 3.92

#Rotatable Bonds: 18

Polar Surface Area: 158.80

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.62

CX Basic pKa: 1.72

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.13

Np Likeness Score: 0.00

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