(2S,3S,4S,5R,6S)-6-((6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carbonyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

ID: ALA4249790

Chembl Id: CHEMBL4249790

PubChem CID: 121396411

Max Phase: Preclinical

Molecular Formula: C25H24ClNO9

Molecular Weight: 517.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c1c[nH]c2cc(Cl)c(-c3ccc(C4(O)CCC4)cc3)cc12

Standard InChI:  InChI=1S/C25H24ClNO9/c26-16-9-17-14(8-13(16)11-2-4-12(5-3-11)25(34)6-1-7-25)15(10-27-17)23(33)36-24-20(30)18(28)19(29)21(35-24)22(31)32/h2-5,8-10,18-21,24,27-30,34H,1,6-7H2,(H,31,32)/t18-,19-,20+,21-,24-/m0/s1

Standard InChI Key:  LTLTUJCGZGVBTO-DCIKREJASA-N

Alternative Forms

1. Parent:

   

   ALA4249790

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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: 517.92

Molecular Weight (Monoisotopic): 517.1140

AlogP: 1.91

#Rotatable Bonds: 5

Polar Surface Area: 169.54

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.33

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: -1.12

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: 0.94

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

Source(1):

• Scientific Literature