9H-beta-Carboline-3-carboxylic acid

ID: ALA11908

Chembl Id: CHEMBL11908

Max Phase: Preclinical

Molecular Formula: C12H8N2O2

Molecular Weight: 212.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c3ccccc3nc-2c[nH]1

Standard InChI:  InChI=1S/C12H8N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-6,13H,(H,15,16)

Standard InChI Key:  AQDZTJDUYKBYKF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA11908

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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

Calculated Properties

Molecular Weight: 212.21

Molecular Weight (Monoisotopic): 212.0586

AlogP: 2.37

#Rotatable Bonds: 1

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: 2.82

CX Basic pKa: 4.53

CX LogP: 1.16

CX LogD: -1.16

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.65

Np Likeness Score: -0.37

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. Bianucci AM, Da Settimo A, Da Settimo F, Primofiore G, Martini C, Giannaccini G, Lucacchini A..  (1992)  Benzodiazepine receptor affinity and interaction of some N-(indol-3-ylglyoxylyl)amine derivatives.,  35  (12): [PMID:1319492] [10.1021/jm00090a011]

3. Lippke KP, Schunack WG, Wenning W, Müller WE..  (1983)  beta-Carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of beta-carboline-3-carboxylic acid.,  26  (4): [PMID:6300400] [10.1021/jm00358a008]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Chen YF, Lin YC, Chen JP, Chan HC, Hsu MH, Lin HY, Kuo SC, Huang LJ..  (2015)  Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents.,  25  (18): [PMID:26235951] [10.1016/j.bmcl.2015.07.058]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays