2-methylnorharmane iodide

ID: ALA455600

PubChem CID: 11529672

Max Phase: Preclinical

Molecular Formula: C12H11IN2

Molecular Weight: 183.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Methylnorharmane Iodide | 2-methylnorharmane iodide|CHEMBL455600|AKOS024332881|2-methyl-9H-pyrido[3,4-b]indol-2-ium;iodide

Canonical SMILES:  C[n+]1ccc2c(c1)[nH]c1ccccc12.[I-]

Standard InChI:  InChI=1S/C12H10N2.HI/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14;/h2-8H,1H3;1H

Standard InChI Key:  UUUXZXBTEIHVDB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   -0.2494    0.8437    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269    1.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9281    0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168    1.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032    1.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5029    0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144    0.3860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7148    1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084    1.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697    1.8956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5593    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3796    2.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    1.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8 10  1  0
  9  6  1  0
  4  7  2  0
  9 10  2  0
  6  5  2  0
 10 11  1  0
  5  2  1  0
 11 12  2  0
  6  7  1  0
 12 13  1  0
  2  3  2  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
  3  4  1  0
M  CHG  2   1  -1  12   1
M  END

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

Calculated Properties

Molecular Weight: 183.23

Molecular Weight (Monoisotopic): 183.0917

AlogP: 2.15

#Rotatable Bonds: ┄

Polar Surface Area: 19.67

Molecular Species: NEUTRAL

HBA: ┄

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.49

CX Basic pKa: ┄

CX LogP: -2.07

CX LogD: -2.07

Aromatic Rings: 3

Heavy Atoms: 14

QED Weighted: 0.52

Np Likeness Score: 0.85

References

1. 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]

2. Van Baelen G, Hostyn S, Dhooghe L, Tapolcsányi P, Mátyus P, Lemière G, Dommisse R, Kaiser M, Brun R, Cos P, Maes L, Hajós G, Riedl Z, Nagy I, Maes BU, Pieters L..  (2009)  Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.,  17  (20): [PMID:19781948] [10.1016/j.bmc.2009.08.057]

3. Rook Y, Schmidtke KU, Gaube F, Schepmann D, Wünsch B, Heilmann J, Lehmann J, Winckler T..  (2010)  Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents.,  53  (9): [PMID:20361801] [10.1021/jm1000024]

4. 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]

Source

Source(1):

• Scientific Literature