2-cyclopentyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid

ID: ALA4125686

Chembl Id: CHEMBL4125686

PubChem CID: 145960580

Max Phase: Preclinical

Molecular Formula: C19H18N2O2

Molecular Weight: 306.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(-c2c[nH]c3ncccc23)cc1C1CCCC1

Standard InChI:  InChI=1S/C19H18N2O2/c22-19(23)15-8-7-13(10-16(15)12-4-1-2-5-12)17-11-21-18-14(17)6-3-9-20-18/h3,6-12H,1-2,4-5H2,(H,20,21)(H,22,23)

Standard InChI Key:  QLMHELCDKYDUPA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4125686

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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: 306.37

Molecular Weight (Monoisotopic): 306.1368

AlogP: 4.59

#Rotatable Bonds: 3

Polar Surface Area: 65.98

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: 3.38

CX LogP: 3.80

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -0.24

References

1. Price DJ, Drewry DH, Schaller LT, Thompson BD, Reid PR, Maloney PR, Liang X, Banker P, Buckholz RG, Selley PK, McDonald OB, Smith JL, Shearer TW, Cox RF, Williams SP, Reid RA, Tacconi S, Faggioni F, Piubelli C, Sartori I, Tessari M, Wang TY..  (2018)  An orally available, brain-penetrant CAMKK2 inhibitor reduces food intake in rodent model.,  28  (10): [PMID:29653895] [10.1016/j.bmcl.2018.03.034]

2. Eduful BJ, O'Byrne SN, Temme L, Asquith CRM, Liang Y, Picado A, Pilotte JR, Hossain MA, Wells CI, Zuercher WJ, Catta-Preta CMC, Zonzini Ramos P, Santiago AS, Couñago RM, Langendorf CG, Nay K, Oakhill JS, Pulliam TL, Lin C, Awad D, Willson TM, Frigo DE, Scott JW, Drewry DH..  (2021)  Hinge Binder Scaffold Hopping Identifies Potent Calcium/Calmodulin-Dependent Protein Kinase Kinase 2 (CAMKK2) Inhibitor Chemotypes.,  64  (15.0): [PMID:34264658] [10.1021/acs.jmedchem.0c02274]

Source

Source(1):

• Scientific Literature