adamantane-1-carboxylic acid (1-oxo-2,3,4,9-tetrahydro-1H-beta-carbolin-6-yl)-amide

ID: ALA388669

Chembl Id: CHEMBL388669

PubChem CID: 44431050

Max Phase: Preclinical

Molecular Formula: C22H25N3O2

Molecular Weight: 363.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCCc2c1[nH]c1ccc(NC(=O)C34CC5CC(CC(C5)C3)C4)cc21

Standard InChI:  InChI=1S/C22H25N3O2/c26-20-19-16(3-4-23-20)17-8-15(1-2-18(17)25-19)24-21(27)22-9-12-5-13(10-22)7-14(6-12)11-22/h1-2,8,12-14,25H,3-7,9-11H2,(H,23,26)(H,24,27)

Standard InChI Key:  VGMKPNBVRYPNKH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA388669

   N-(1-oxo-2,3,4,9-tetrahydropyrido[3,4-b]indol-6-yl)adamantane-1-carboxamide

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: 363.46

Molecular Weight (Monoisotopic): 363.1947

AlogP: 3.61

#Rotatable Bonds: 2

Polar Surface Area: 73.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: ┄

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.41

References

1. Di Fabio R, Micheli F, Alvaro G, Cavanni P, Donati D, Gagliardi T, Fontana G, Giovannini R, Maffeis M, Mingardi A, Tranquillini ME, Vitulli G..  (2007)  From pyrroles to 1-oxo-2,3,4,9-tetrahydro-1H-beta-carbolines: a new class of orally bioavailable mGluR1 antagonists.,  17  (8): [PMID:17276684] [10.1016/j.bmcl.2007.01.055]

2. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(1):

• Scientific Literature