Methyl 6-deoxy-6-[(3-guanidinopropyl)sulfonyl]-alpha-D-glucopyranoside

ID: ALA4172694

Chembl Id: CHEMBL4172694

PubChem CID: 145952051

Max Phase: Preclinical

Molecular Formula: C11H23N3O7S

Molecular Weight: 341.39

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H23N3O7S/c1-20-10-9(17)8(16)7(15)6(21-10)5-22(18,19)4-2-3-14-11(12)13/h6-10,15-17H,2-5H2,1H3,(H4,12,13,14)/t6-,7-,8+,9-,10+/m1/s1

Standard InChI Key:  LXVWBHINTPXQCH-SPFKKGSWSA-N

Alternative Forms

  1. Parent:

    ALA4172694

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Associated Targets(Human)

G6PD Tchem Glucose-6-phosphate 1-dehydrogenase (778 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

GluPho Bifunctional glucose-6-phosphate 1-dehydrogenase/6-phosphogluconolactonase (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 341.39Molecular Weight (Monoisotopic): 341.1257AlogP: -3.27#Rotatable Bonds: 7
Polar Surface Area: 175.19Molecular Species: BASEHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 7#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.22CX Basic pKa: 11.70CX LogP: -4.28CX LogD: -6.25
Aromatic Rings: Heavy Atoms: 22QED Weighted: 0.16Np Likeness Score: 0.95

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