ID: ALA1132

Max Phase: Phase

Molecular Formula: C9H12N2

Molecular Weight: 148.21

Molecule Type: Small molecule

Representations

Synonyms (4): 1'-demethylnicotine | 3-(2-pyrrolidinyl)-(s)-pyridine | Nicotine related compound f | Nornicotine
Synonyms from Alternative Forms(4):

Canonical SMILES:  c1cncc(C2CCCN2)c1

Standard InChI:  InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

Standard InChI Key:  MYKUKUCHPMASKF-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 148.21

Molecular Weight (Monoisotopic): 148.1000

AlogP: 1.51

#Rotatable Bonds: 1

Polar Surface Area: 24.92

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.92

CX LogP: 0.78

CX LogD: -1.67

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.65

Np Likeness Score: -0.09

References

1. Schmitt JD, Sharples CG, Caldwell WS..  (1999)  Molecular recognition in nicotinic acetylcholine receptors: the importance of pi-cation interactions.,  42  (16): [PMID:10447950] [10.1021/jm990093z]

2. Kanne DB, Abood LG..  (1988)  Synthesis and biological characterization of pyridohomotropanes. Structure-activity relationships of conformationally restricted nicotinoids.,  31  (3): [PMID:3346870] [10.1021/jm00398a004]

3. Ferretti G, Dukat M, Giannella M, Piergentili A, Pigini M, Quaglia W, Damaj MI, Martin BR, Glennon RA..  (2003)  Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors.,  13  (4): [PMID:12639569] [10.1016/s0960-894x(02)01031-4]

4. Kanne DB, Tomizawa M, Durkin KA, Casida JE..  (2005)  6'-Methylpyrido[3,4-b]norhomotropane: synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model.,  15  (4): [PMID:15686879] [10.1016/j.bmcl.2004.12.069]

5. Dukat M, Ramunno A, Banzi R, Damaj MI, Martin B, Glennon RA..  (2005)  3-(2-Aminoethyl)pyridine analogs as alpha4beta2 nicotinic cholinergic receptor ligands.,  15  (19): [PMID:16039854] [10.1016/j.bmcl.2005.06.053]

6. PubChem BioAssay data set, 

7. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]

8. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]

9. Unpublished dataset, 

10. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

11. Lin SX,Curtis MA,Sperry J.  (2020)  Pyridine alkaloids with activity in the central nervous system.,  28  (24): [PMID:33120080] [10.1016/j.bmc.2020.115820]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• CO-ADD antimicrobial screening data