Methyl 6-[(2-cyanoethyl)thio]-6-deoxy-alpha-D-glucopyranoside

ID: ALA4159624

Chembl Id: CHEMBL4159624

PubChem CID: 145958859

Max Phase: Preclinical

Molecular Formula: C10H17NO5S

Molecular Weight: 263.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CSCCC#N)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H17NO5S/c1-15-10-9(14)8(13)7(12)6(16-10)5-17-4-2-3-11/h6-10,12-14H,2,4-5H2,1H3/t6-,7-,8+,9-,10+/m1/s1

Standard InChI Key:  XRCNEXYBECNMJZ-SPFKKGSWSA-N

Alternative Forms

1. Parent:

   

   ALA4159624

   ---

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: 263.31

Molecular Weight (Monoisotopic): 263.0827

AlogP: -0.91

#Rotatable Bonds: 5

Polar Surface Area: 102.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: -1.14

CX LogD: -1.14

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.55

Np Likeness Score: 1.06

References

1. Alencar N, Sola I, Linares M, Juárez-Jiménez J, Pont C, Viayna A, Vílchez D, Sampedro C, Abad P, Pérez-Benavente S, Lameira J, Bautista JM, Muñoz-Torrero D, Luque FJ..  (2018)  First homology model of Plasmodium falciparum glucose-6-phosphate dehydrogenase: Discovery of selective substrate analog-based inhibitors as novel antimalarial agents.,  146  [PMID:29407943] [10.1016/j.ejmech.2018.01.044]

2. Koperniku A, Garcia AA, Mochly-Rosen D..  (2022)  Boosting the Discovery of Small Molecule Inhibitors of Glucose-6-Phosphate Dehydrogenase for the Treatment of Cancer, Infectious Diseases, and Inflammation.,  65  (6.0): [PMID:35239352] [10.1021/acs.jmedchem.1c01577]

Source

Source(1):

• Scientific Literature