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

ID: ALA4218273

Chembl Id: CHEMBL4218273

PubChem CID: 145969389

Max Phase: Preclinical

Molecular Formula: C34H41Cl2FN2O11

Molecular Weight: 743.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2ccc(NC(=O)COC(=O)CCCc3ccc(N(CCCl)CCCl)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C34H41Cl2FN2O11/c1-21(40)45-19-28-32(47-22(2)41)33(48-23(3)42)31(37)34(50-28)49-27-13-9-25(10-14-27)38-29(43)20-46-30(44)6-4-5-24-7-11-26(12-8-24)39(17-15-35)18-16-36/h7-14,28,31-34H,4-6,15-20H2,1-3H3,(H,38,43)/t28-,31-,32-,33-,34-/m1/s1

Standard InChI Key:  WUENLBJBIKOCLS-BNNJPYFFSA-N

Alternative Forms

1. Parent:

   

   ALA4218273

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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: 743.61

Molecular Weight (Monoisotopic): 742.2071

AlogP: 4.34

#Rotatable Bonds: 18

Polar Surface Area: 156.00

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.33

CX Basic pKa: 1.72

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.13

Np Likeness Score: 0.05

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