ID: ALA6655

Max Phase: Preclinical

Molecular Formula: C17H18BrN3O3

Molecular Weight: 392.25

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN1Cc2c(C(=O)OC(C)(C)C)ncn2-c2ccc(Br)cc2C1=O

Standard InChI:  InChI=1S/C17H18BrN3O3/c1-17(2,3)24-16(23)14-13-8-20(4)15(22)11-7-10(18)5-6-12(11)21(13)9-19-14/h5-7,9H,8H2,1-4H3

Standard InChI Key:  IXGIOXIKQZCZIK-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: 392.25

Molecular Weight (Monoisotopic): 391.0532

AlogP: 3.18

#Rotatable Bonds: 1

Polar Surface Area: 64.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.86

CX LogP: 2.72

CX LogD: 2.72

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -0.24

References

1. Gu ZQ, Wong G, Dominguez C, de Costa BR, Rice KC, Skolnick P..  (1993)  Synthesis and evaluation of imidazo[1,5-a][1,4]benzodiazepine esters with high affinities and selectivities at "diazepam-insensitive" benzodiazepine receptors.,  36  (8): [PMID:8386769] [10.1021/jm00060a007]

2. Liu R, Hu RJ, Zhang P, Skolnick P, Cook JM..  (1996)  Synthesis and pharmacological properties of novel 8-substituted imidazobenzodiazepines: high-affinity, selective probes for alpha 5-containing GABAA receptors.,  39  (9): [PMID:8627617] [10.1021/jm950887n]

3. Huang Q, Liu R, Zhang P, He X, McKernan R, Gan T, Bennett DW, Cook JM..  (1998)  Predictive models for GABAA/benzodiazepine receptor subtypes: studies of quantitative structure-activity relationships for imidazobenzodiazepines at five recombinant GABAA/benzodiazepine receptor subtypes [alphaxbeta3gamma2 (x = 1-3, 5, and 6)] via comparative molecular field analysis.,  41  (21): [PMID:9767648] [10.1021/jm980317y]

4. 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]

Source

Source(1):

• Scientific Literature