3-(3,4,6-Tri-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranosylamino)-3-oxopropanoic acid

ID: ALA4207756

Chembl Id: CHEMBL4207756

PubChem CID: 145976703

Max Phase: Preclinical

Molecular Formula: C28H37Cl2FN2O10

Molecular Weight: 651.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](NC(=O)COC(=O)CCCc2ccc(N(CCCl)CCCl)cc2)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C28H37Cl2FN2O10/c1-17(34)39-15-22-26(41-18(2)35)27(42-19(3)36)25(31)28(43-22)32-23(37)16-40-24(38)6-4-5-20-7-9-21(10-8-20)33(13-11-29)14-12-30/h7-10,22,25-28H,4-6,11-16H2,1-3H3,(H,32,37)/t22-,25-,26-,27-,28-/m1/s1

Standard InChI Key:  ARCPSQAXNNIQPR-DVVXUNHVSA-N

Alternative Forms

1. Parent:

   

   ALA4207756

   ---

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: 651.51

Molecular Weight (Monoisotopic): 650.1809

AlogP: 2.44

#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: 11.40

CX Basic pKa: 1.72

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: 0.23

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