(2S,3S,4S,5R,6S)-6-((6-Chloro-5-(6-(dimethylamino)-2-methoxypyridin-3-yl)-1H-indole-3-carbonyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic Acid

ID: ALA4250253

Chembl Id: CHEMBL4250253

PubChem CID: 121396412

Max Phase: Preclinical

Molecular Formula: C23H24ClN3O9

Molecular Weight: 521.91

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1nc(N(C)C)ccc1-c1cc2c(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c[nH]c2cc1Cl

Standard InChI:  InChI=1S/C23H24ClN3O9/c1-27(2)15-5-4-9(20(26-15)34-3)10-6-11-12(8-25-14(11)7-13(10)24)22(33)36-23-18(30)16(28)17(29)19(35-23)21(31)32/h4-8,16-19,23,25,28-30H,1-3H3,(H,31,32)/t16-,17-,18+,19-,23-/m0/s1

Standard InChI Key:  YJKYSCKYOBZSRV-ZFXLNCEJSA-N

Alternative Forms

  1. Parent:

    ALA4250253

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Associated Targets(Human)

Hepatocyte (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAG1 Tchem AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMPK alpha2/beta1/gamma1 (210 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAB2 Tchem AMPK alpha1/beta2/gamma1 (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMPK alpha2/beta2/gamma1 (80 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMPK alpha2/beta2/gamma3 (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAB1 Tchem AMP-activated protein kinase, beta-1 subunit (56 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: 521.91Molecular Weight (Monoisotopic): 521.1201AlogP: 1.01#Rotatable Bonds: 6
Polar Surface Area: 174.67Molecular Species: ACIDHBA: 10HBD: 5
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 5#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.31CX Basic pKa: 5.01CX LogP: 1.10CX LogD: -1.26
Aromatic Rings: 3Heavy Atoms: 36QED Weighted: 0.29Np Likeness Score: 0.38

References

1. Ryder TF, Calabrese MF, Walker GS, Cameron KO, Reyes AR, Borzilleri KA, Delmore J, Miller R, Kurumbail RG, Ward J, Kung DW, Brown JA, Edmonds DJ, Eng H, Wolford AC, Kalgutkar AS..  (2018)  Acyl Glucuronide Metabolites of 6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1 H-indole-3-carboxylic Acid (PF-06409577) and Related Indole-3-carboxylic Acid Derivatives are Direct Activators of Adenosine Monophosphate-Activated Protein Kinase (AMPK).,  61  (16): [PMID:30036059] [10.1021/acs.jmedchem.8b00807]

Source