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

ID: ALA4205591

Chembl Id: CHEMBL4205591

PubChem CID: 145978774

Max Phase: Preclinical

Molecular Formula: C35H43Cl2FN4O10

Molecular Weight: 769.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](NC(=O)c2ccc(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/C35H43Cl2FN4O10/c1-21(43)49-20-28-32(50-22(2)44)33(51-23(3)45)31(38)35(52-28)41-34(48)25-9-11-26(12-10-25)40-30(47)19-39-29(46)6-4-5-24-7-13-27(14-8-24)42(17-15-36)18-16-37/h7-14,28,31-33,35H,4-6,15-20H2,1-3H3,(H,39,46)(H,40,47)(H,41,48)/t28-,31-,32-,33-,35-/m1/s1

Standard InChI Key:  FUBUXWQMEHFMSV-AGFYRQSKSA-N

Alternative Forms

1. Parent:

   

   ALA4205591

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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: 769.65

Molecular Weight (Monoisotopic): 768.2340

AlogP: 3.27

#Rotatable Bonds: 18

Polar Surface Area: 178.67

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.49

CX Basic pKa: 1.72

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.12

Np Likeness Score: -0.17

References

1. 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