ID: ALA49141

Max Phase: Preclinical

Molecular Formula: C19H22N2O4

Molecular Weight: 342.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCOc1ccc2[nH]c3cnc(C(=O)OCC)c(COC)c3c2c1

Standard InChI:  InChI=1S/C19H22N2O4/c1-4-8-25-12-6-7-15-13(9-12)17-14(11-23-3)18(19(22)24-5-2)20-10-16(17)21-15/h6-7,9-10,21H,4-5,8,11H2,1-3H3

Standard InChI Key:  WRXDVVALWQGPMW-UHFFFAOYSA-N

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

Properties

Molecular Weight: 342.40

Molecular Weight (Monoisotopic): 342.1580

AlogP: 3.83

#Rotatable Bonds: 7

Polar Surface Area: 73.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.73

CX Basic pKa: 2.10

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -0.34

References

1. Diaz-Arauzo H, Evoniuk GE, Skolnick P, Cook JM..  (1991)  The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic.,  34  (5): [PMID:1674542] [10.1021/jm00109a035]

2. Cox ED, Diaz-Arauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM..  (1998)  Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors.,  41  (14): [PMID:9651158] [10.1021/jm970460b]

3. Huang Q, He X, Ma C, Liu R, Yu S, Dayer CA, Wenger GR, McKernan R, Cook JM..  (2000)  Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach.,  43  (1): [PMID:10633039] [10.1021/jm990341r]

4. 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