ID: ALA504850

Max Phase: Preclinical

Molecular Formula: C13H10N2O2

Molecular Weight: 226.24

Molecule Type: Small molecule

Representations

Synonyms (1): Harman-3-Carboxylic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1nc(C(=O)O)cc2c1[nH]c1ccccc12

Standard InChI:  InChI=1S/C13H10N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-6,15H,1H3,(H,16,17)

Standard InChI Key:  MFEZJNMQTQMDRQ-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: 226.24

Molecular Weight (Monoisotopic): 226.0742

AlogP: 2.72

#Rotatable Bonds: 1

Polar Surface Area: 65.98

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.39

CX Basic pKa: 5.56

CX LogP: 0.60

CX LogD: -1.04

Aromatic Rings: 3

Heavy Atoms: 17

QED Weighted: 0.67

Np Likeness Score: 0.06

References

1. Cardoso CL, Castro-Gamboa I, Silva DH, Furlan M, Epifanio Rde A, Pinto Ada C, Moraes de Rezende C, Lima JA, Bolzani Vda S..  (2004)  Indole glucoalkaloids from Chimarrhis turbinata and their evaluation as antioxidant agents and acetylcholinesterase inhibitors.,  67  (11): [PMID:15568781] [10.1021/np049863m]

2. PubChem BioAssay data set, 

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. Sasaki T, Li W, Higai K, Koike K..  (2015)  Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.,  25  (9): [PMID:25819098] [10.1016/j.bmcl.2015.03.014]

5. Hu X, Gao X, Gao G, Wang Y, Cao H, Li D, Hua H..  (2021)  Discovery of β-carboline-(phenylsulfonyl)furoxan hybrids as potential anti-breast cancer agents.,  40  [PMID:33744443] [10.1016/j.bmcl.2021.127952]

6. Zhang H, Zhang RH, Liao XM, Yang D, Wang YC, Zhao YL, Xu GB, Liu CH, Li YJ, Liao SG, Zhou M..  (2021)  Discovery of β-Carboline Derivatives as a Highly Potent Cardioprotectant against Myocardial Ischemia-Reperfusion Injury.,  64  (13.0): [PMID:34132541] [10.1021/acs.jmedchem.1c00384]

7. Dai JK, Dan WJ, Wan JB..  (2022)  Natural and synthetic β-carboline as a privileged antifungal scaffolds.,  229  [PMID:34954591] [10.1016/j.ejmech.2021.114057]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays