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

ID: ALA4205269

Chembl Id: CHEMBL4205269

PubChem CID: 145977852

Max Phase: Preclinical

Molecular Formula: C35H42Cl2FN3O12

Molecular Weight: 786.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](OC(=O)NCC(=O)Nc2ccc(OC(=O)CCCc3ccc(N(CCCl)CCCl)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C35H42Cl2FN3O12/c1-21(42)48-20-28-32(49-22(2)43)33(50-23(3)44)31(38)34(52-28)53-35(47)39-19-29(45)40-25-9-13-27(14-10-25)51-30(46)6-4-5-24-7-11-26(12-8-24)41(17-15-36)18-16-37/h7-14,28,31-34H,4-6,15-20H2,1-3H3,(H,39,47)(H,40,45)/t28-,31-,32-,33-,34+/m1/s1

Standard InChI Key:  MPBVTUWEKKPRQI-MQEMTDQLSA-N

Alternative Forms

1. Parent:

   

   ALA4205269

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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: 786.63

Molecular Weight (Monoisotopic): 785.2130

AlogP: 4.05

#Rotatable Bonds: 18

Polar Surface Area: 185.10

Molecular Species: NEUTRAL

HBA: 13

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.81

CX Basic pKa: 1.72

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 2

Heavy Atoms: 53

QED Weighted: 0.10

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