ID: ALA499836

Max Phase: Preclinical

Molecular Formula: C12H10ClIN2

Molecular Weight: 217.68

Molecule Type: Small molecule

Representations

Synonyms (3): Nostacarboline Iodide | Nostocarboline | Nostocarboline Hydroiodide
Synonyms from Alternative Forms(3):

Canonical SMILES:  C[n+]1ccc2c(c1)[nH]c1ccc(Cl)cc12.[I-]

Standard InChI:  InChI=1S/C12H9ClN2.HI/c1-15-5-4-9-10-6-8(13)2-3-11(10)14-12(9)7-15;/h2-7H,1H3;1H

Standard InChI Key:  YSZAXPOWTBYIJG-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: 217.68

Molecular Weight (Monoisotopic): 217.0527

AlogP: 2.80

#Rotatable Bonds: 0

Polar Surface Area: 19.67

Molecular Species: NEUTRAL

HBA: 0

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.37

CX Basic pKa:

CX LogP: -1.47

CX LogD: -1.47

Aromatic Rings: 3

Heavy Atoms: 15

QED Weighted: 0.56

Np Likeness Score: 0.44

References

1. Barbaras D, Kaiser M, Brun R, Gademann K..  (2008)  Potent and selective antiplasmodial activity of the cyanobacterial alkaloid nostocarboline and its dimers.,  18  (15): [PMID:18606541] [10.1016/j.bmcl.2008.06.049]

2. Becher PG, Beuchat J, Gademann K, Jüttner F..  (2005)  Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A.,  68  (12): [PMID:16378379] [10.1021/np050312l]

3. Becher PG, Beuchat J, Gademann K, Jüttner F..  (2005)  Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A.,  68  (12): [PMID:16378379] [10.1021/np050312l]

4. Bonazzi S, Barbaras D, Patiny L, Scopelliti R, Schneider P, Cole ST, Kaiser M, Brun R, Gademann K..  (2010)  Antimalarial and antitubercular nostocarboline and eudistomin derivatives: synthesis, in vitro and in vivo biological evaluation.,  18  (4): [PMID:20133138] [10.1016/j.bmc.2010.01.013]

5. Suzuki K, Nomura I, Ninomiya M, Tanaka K, Koketsu M..  (2018)  Synthesis and antimicrobial activity of β-carboline derivatives with N2-alkyl modifications.,  28  (17): [PMID:30001916] [10.1016/j.bmcl.2018.06.050]

6. Dai J, Dan W, Schneider U, Wang J..  (2018)  β-Carboline alkaloid monomers and dimers: Occurrence, structural diversity, and biological activities.,  157  [PMID:30125723] [10.1016/j.ejmech.2018.08.027]

Source

Source(1):

• Scientific Literature