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

ID: ALA4203376

Chembl Id: CHEMBL4203376

PubChem CID: 145505509

Max Phase: Preclinical

Molecular Formula: C34H42Cl2FN3O10

Molecular Weight: 742.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2ccc(NC(=O)CC(=O)NCCCc3ccc(N(CCCl)CCCl)cc3)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C34H42Cl2FN3O10/c1-21(41)46-20-28-32(47-22(2)42)33(48-23(3)43)31(37)34(50-28)49-27-12-8-25(9-13-27)39-30(45)19-29(44)38-16-4-5-24-6-10-26(11-7-24)40(17-14-35)18-15-36/h6-13,28,31-34H,4-5,14-20H2,1-3H3,(H,38,44)(H,39,45)/t28-,31-,32-,33-,34-/m1/s1

Standard InChI Key:  GGUGLRGUWLMOBI-BNNJPYFFSA-N

Alternative Forms

1. Parent:

   

   ALA4203376

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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: 742.62

Molecular Weight (Monoisotopic): 741.2231

AlogP: 3.92

#Rotatable Bonds: 18

Polar Surface Area: 158.80

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.95

CX Basic pKa: 1.72

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.08

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