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

ID: ALA4202444

Chembl Id: CHEMBL4202444

PubChem CID: 145976733

Max Phase: Preclinical

Molecular Formula: C33H39Cl2FN2O10

Molecular Weight: 713.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](OC(=O)c2ccc(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/C33H39Cl2FN2O10/c1-20(39)44-19-27-30(45-21(2)40)31(46-22(3)41)29(36)33(47-27)48-32(43)24-9-11-25(12-10-24)37-28(42)6-4-5-23-7-13-26(14-8-23)38(17-15-34)18-16-35/h7-14,27,29-31,33H,4-6,15-19H2,1-3H3,(H,37,42)/t27-,29-,30-,31-,33+/m1/s1

Standard InChI Key:  RHEIKDACZYBRRR-PTXWAVMNSA-N

Alternative Forms

1. Parent:

   

   ALA4202444

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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: 713.58

Molecular Weight (Monoisotopic): 712.1966

AlogP: 4.58

#Rotatable Bonds: 16

Polar Surface Area: 146.77

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.42

CX Basic pKa: 1.72

CX LogP: 5.18

CX LogD: 5.18

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.15

Np Likeness Score: 0.18

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