4-(4-{4-[Bis(2-chloroethyl)amino]phenyl}butamido)-N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranosyloxy)phenyl]benzamide

ID: ALA4208248

Chembl Id: CHEMBL4208248

PubChem CID: 145505505

Max Phase: Preclinical

Molecular Formula: C39H44Cl2FN3O10

Molecular Weight: 804.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2ccc(NC(=O)c3ccc(NC(=O)CCCc4ccc(N(CCCl)CCCl)cc4)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C39H44Cl2FN3O10/c1-24(46)51-23-33-36(52-25(2)47)37(53-26(3)48)35(42)39(55-33)54-32-17-13-30(14-18-32)44-38(50)28-9-11-29(12-10-28)43-34(49)6-4-5-27-7-15-31(16-8-27)45(21-19-40)22-20-41/h7-18,33,35-37,39H,4-6,19-23H2,1-3H3,(H,43,49)(H,44,50)/t33-,35-,36-,37-,39-/m1/s1

Standard InChI Key:  ZFPUXOJZYATOCP-FBBCAKTNSA-N

Alternative Forms

1. Parent:

   

   ALA4208248

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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: 804.70

Molecular Weight (Monoisotopic): 803.2388

AlogP: 6.05

#Rotatable Bonds: 18

Polar Surface Area: 158.80

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.53

CX Basic pKa: 1.72

CX LogP: 6.11

CX LogD: 6.11

Aromatic Rings: 3

Heavy Atoms: 55

QED Weighted: 0.09

Np Likeness Score: -0.03

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