ID: ALA273491

Max Phase: Preclinical

Molecular Formula: C19H14N2O2

Molecular Weight: 302.33

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)c1cc2c([nH]c3ccccc32)c(-c2ccccc2)n1

Standard InChI:  InChI=1S/C19H14N2O2/c1-23-19(22)16-11-14-13-9-5-6-10-15(13)20-18(14)17(21-16)12-7-3-2-4-8-12/h2-11,20H,1H3

Standard InChI Key:  SPYRHCLAUAASCR-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 302.33

Molecular Weight (Monoisotopic): 302.1055

AlogP: 4.17

#Rotatable Bonds: 2

Polar Surface Area: 54.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.97

CX Basic pKa: 1.65

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: -0.18

References

1. Cain M, Weber RW, Guzman F, Cook JM, Barker SA, Rice KC, Crawley JN, Paul SM, Skolnick P..  (1982)  Beta-carbolines: synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors.,  25  (9): [PMID:6127411] [10.1021/jm00351a015]

2. Guzman F, Cain M, Larscheid P, Hagen T, Cook JM, Schweri M, Skolnick P, Paul SM..  (1984)  Biomimetic approach to potential benzodiazepine receptor agonists and antagonists.,  27  (5): [PMID:6325688] [10.1021/jm00371a002]

3. Zeng Y, Zhang Y, Weng Q, Hu M, Zhong G..  (2010)  Cytotoxic and insecticidal activities of derivatives of harmine, a natural insecticidal component isolated from Peganum harmala.,  15  (11): [PMID:21060288] [10.3390/molecules15117775]

4. Zhao Y, Ye F, Xu J, Liao Q, Chen L, Zhang W, Sun H, Liu W, Feng F, Qu W..  (2018)  Design, synthesis and evaluation of novel bivalent β-carboline derivatives as multifunctional agents for the treatment of Alzheimer's disease.,  26  (13): [PMID:29960728] [10.1016/j.bmc.2018.06.018]

5. Panice MR, Lopes SMM, Figueiredo MC, Goes Ruiz ALT, Foglio MA, Nazari Formagio AS, Sarragiotto MH, Pinho E Melo TMVD..  (2019)  New 3-tetrazolyl-β-carbolines and β-carboline-3-carboxylates with anti-cancer activity.,  179  [PMID:31247374] [10.1016/j.ejmech.2019.05.085]

6. Lopes-Ortiz MA, Panice MR, Borges de Melo E, Ataide Martins JP, Baldin VP, Agostinho Pires CT, Caleffi-Ferracioli KR, Dias Siqueira VL, Bertin de Lima Scodro R, Sarragiotto MH, Cardoso RF..  (2020)  Synthesis and anti-Mycobacterium tuberculosis activity of imide-β-carboline and carbomethoxy-β-carboline derivatives.,  187  [PMID:31816556] [10.1016/j.ejmech.2019.111935]

Source

Source(1):

• Scientific Literature