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

ID: ALA4218156

Chembl Id: CHEMBL4218156

PubChem CID: 69172865

Max Phase: Preclinical

Molecular Formula: C35H43Cl2FN4O11

Molecular Weight: 785.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](OC(=O)NCC(=O)Nc2ccc(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/C35H43Cl2FN4O11/c1-21(43)49-20-28-32(50-22(2)44)33(51-23(3)45)31(38)34(52-28)53-35(48)39-19-30(47)41-26-11-9-25(10-12-26)40-29(46)6-4-5-24-7-13-27(14-8-24)42(17-15-36)18-16-37/h7-14,28,31-34H,4-6,15-20H2,1-3H3,(H,39,48)(H,40,46)(H,41,47)/t28-,31-,32-,33-,34+/m1/s1

Standard InChI Key:  JYWLHYMYVPCJAJ-MQEMTDQLSA-N

Alternative Forms

1. Parent:

   

   ALA4218156

   [(2R,3R,4S,5R,6S)-3,4-diacetyloxy-6-[[2-[4-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]anilino]-2-oxoethyl]carbamoyloxy]-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: 785.65

Molecular Weight (Monoisotopic): 784.2289

AlogP: 4.09

#Rotatable Bonds: 18

Polar Surface Area: 187.90

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.86

CX Basic pKa: 1.72

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 2

Heavy Atoms: 53

QED Weighted: 0.11

Np Likeness Score: -0.04

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