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

ID: ALA4172838

PubChem CID: 145950768

Max Phase: Preclinical

Molecular Formula: C9H19NO5S

Molecular Weight: 253.32

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CSCCN)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C9H19NO5S/c1-14-9-8(13)7(12)6(11)5(15-9)4-16-3-2-10/h5-9,11-13H,2-4,10H2,1H3/t5-,6-,7+,8-,9+/m1/s1

Standard InChI Key:  LCXDXQFHBZYKPJ-ZEBDFXRSSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    7.8547   -3.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8547   -5.2314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -6.0511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180   -5.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -3.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -3.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -4.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -5.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7241   -4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7241   -3.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180   -3.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3102   -4.0007    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5615   -4.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026   -3.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026   -2.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950   -2.3661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  6  1  1  6
  7  2  1  6
  8  3  1  1
  9  4  1  6
 11 12  1  0
  1 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4172838

    ---

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

Biocomponents

Calculated Properties

Molecular Weight: 253.32Molecular Weight (Monoisotopic): 253.0984AlogP: -1.87#Rotatable Bonds: 5
Polar Surface Area: 105.17Molecular Species: BASEHBA: 7HBD: 4
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 12.22CX Basic pKa: 9.71CX LogP: -1.86CX LogD: -4.10
Aromatic Rings: Heavy Atoms: 16QED Weighted: 0.43Np Likeness Score: 1.48

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