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

ID: ALA4215715

Chembl Id: CHEMBL4215715

PubChem CID: 69174565

Max Phase: Preclinical

Molecular Formula: C33H40Cl2FN3O10

Molecular Weight: 728.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](OC(=O)Nc2ccc(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/C33H40Cl2FN3O10/c1-20(40)45-19-27-30(46-21(2)41)31(47-22(3)42)29(36)32(48-27)49-33(44)38-25-11-9-24(10-12-25)37-28(43)6-4-5-23-7-13-26(14-8-23)39(17-15-34)18-16-35/h7-14,27,29-32H,4-6,15-19H2,1-3H3,(H,37,43)(H,38,44)/t27-,29-,30-,31-,32+/m1/s1

Standard InChI Key:  WPGZAQHZRIOXML-YFLZBMDASA-N

Alternative Forms

1. Parent:

   

   ALA4215715

   [(2R,3R,4S,5R,6S)-3,4-diacetyloxy-6-[[4-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]phenyl]carbamoyloxy]-5-fluorooxan-2-yl]methyl acetate

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: 728.60

Molecular Weight (Monoisotopic): 727.2075

AlogP: 4.97

#Rotatable Bonds: 16

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: 12.97

CX Basic pKa: 1.72

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 49

QED Weighted: 0.14

Np Likeness Score: 0.06

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