methyl 5-(N-(((2R,3S,4R,5R)-5-(3-bromobenzamido)-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)sulfamoyl)-2-methylfuran-3-carboxylate

ID: ALA3806028

Chembl Id: CHEMBL3806028

PubChem CID: 127049887

Max Phase: Preclinical

Molecular Formula: C20H23BrN2O10S

Molecular Weight: 563.38

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(S(=O)(=O)NC[C@H]2OC(O)[C@H](NC(=O)c3cccc(Br)c3)[C@@H](O)[C@@H]2O)oc1C

Standard InChI:  InChI=1S/C20H23BrN2O10S/c1-9-12(19(27)31-2)7-14(32-9)34(29,30)22-8-13-16(24)17(25)15(20(28)33-13)23-18(26)10-4-3-5-11(21)6-10/h3-7,13,15-17,20,22,24-25,28H,8H2,1-2H3,(H,23,26)/t13-,15-,16-,17-,20?/m1/s1

Standard InChI Key:  GGUKCWIKTZNCOC-YFAUVBGMSA-N

Alternative Forms

  1. Parent:

    ALA3806028

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Associated Targets(Human)

HK1 Tchem Hexokinase type I (266 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HK2 Tchem Hexokinase type II (81 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: 563.38Molecular Weight (Monoisotopic): 562.0257AlogP: -0.35#Rotatable Bonds: 7
Polar Surface Area: 184.63Molecular Species: NEUTRALHBA: 10HBD: 5
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 5#RO5 Violations (Lipinski): 2
CX Acidic pKa: 8.17CX Basic pKa: CX LogP: 0.16CX LogD: 0.10
Aromatic Rings: 2Heavy Atoms: 34QED Weighted: 0.28Np Likeness Score: -0.23

References

1. Lin H, Zeng J, Xie R, Schulz MJ, Tedesco R, Qu J, Erhard KF, Mack JF, Raha K, Rendina AR, Szewczuk LM, Kratz PM, Jurewicz AJ, Cecconie T, Martens S, McDevitt PJ, Martin JD, Chen SB, Jiang Y, Nickels L, Schwartz BJ, Smallwood A, Zhao B, Campobasso N, Qian Y, Briand J, Rominger CM, Oleykowski C, Hardwicke MA, Luengo JI..  (2016)  Discovery of a Novel 2,6-Disubstituted Glucosamine Series of Potent and Selective Hexokinase 2 Inhibitors.,  (3): [PMID:26985301] [10.1021/acsmedchemlett.5b00214]

Source