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

ID: ALA4162165

Chembl Id: CHEMBL4162165

PubChem CID: 145959704

Max Phase: Preclinical

Molecular Formula: C10H21N3O5S

Molecular Weight: 295.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CSCCNC(=N)N)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H21N3O5S/c1-17-9-8(16)7(15)6(14)5(18-9)4-19-3-2-13-10(11)12/h5-9,14-16H,2-4H2,1H3,(H4,11,12,13)/t5-,6-,7+,8-,9+/m1/s1

Standard InChI Key:  BDOOKFLCWHPBTQ-ZEBDFXRSSA-N

Alternative Forms

1. Parent:

   

   ALA4162165

   ---

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: 295.36

Molecular Weight (Monoisotopic): 295.1202

AlogP: -2.34

#Rotatable Bonds: 6

Polar Surface Area: 141.05

Molecular Species: BASE

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: 11.69

CX LogP: -2.62

CX LogD: -4.61

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.18

Np Likeness Score: 1.17

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