(S)-4,6-Difluoro-5-(4-(tetrahydro-2H-pyran-2-yl)phenyl)-1H-indole-3-carboxylic Acid

ID: ALA4105032

Chembl Id: CHEMBL4105032

PubChem CID: 121396404

Max Phase: Preclinical

Molecular Formula: C20H17F2NO3

Molecular Weight: 357.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c[nH]c2cc(F)c(-c3ccc([C@@H]4CCCCO4)cc3)c(F)c12

Standard InChI:  InChI=1S/C20H17F2NO3/c21-14-9-15-18(13(10-23-15)20(24)25)19(22)17(14)12-6-4-11(5-7-12)16-3-1-2-8-26-16/h4-7,9-10,16,23H,1-3,8H2,(H,24,25)/t16-/m0/s1

Standard InChI Key:  JQJNGAWEMYQJIQ-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA4105032

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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: 357.36

Molecular Weight (Monoisotopic): 357.1176

AlogP: 5.05

#Rotatable Bonds: 3

Polar Surface Area: 62.32

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.48

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 1.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.22

References

1. Edmonds DJ, Kung DW, Kalgutkar AS, Filipski KJ, Ebner DC, Cabral S, Smith AC, Aspnes GE, Bhattacharya SK, Borzilleri KA, Brown JA, Calabrese MF, Caspers NL, Cokorinos EC, Conn EL, Dowling MS, Eng H, Feng B, Fernando DP, Genung NE, Herr M, Kurumbail RG, Lavergne SY, Lee EC, Li Q, Mathialagan S, Miller RA, Panteleev J, Polivkova J, Rajamohan F, Reyes AR, Salatto CT, Shavnya A, Thuma BA, Tu M, Ward J, Withka JM, Xiao J, Cameron KO..  (2018)  Optimization of Metabolic and Renal Clearance in a Series of Indole Acid Direct Activators of 5'-Adenosine Monophosphate-Activated Protein Kinase (AMPK).,  61  (6): [PMID:29466005] [10.1021/acs.jmedchem.7b01641]

2. 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