Cotinine
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Basic Info
| Common Name | Cotinine(F05158) |
| 2D Structure | |
| Description | Quantitatively, the most important metabolite of nicotine in most mammalian species is cotinine. In humans, about 70 to 80% of nicotine is converted to cotinine. This transformation involves two steps. The first is mediated by a cytochrome P450 system (mainly CYP2A6 and CYP2B6) to produce nicotine iminium ion. The second step is catalyzed by aldehyde oxidase (AOX). A number of cotinine metabolites have also been structurally characterized. Indeed, it appears that most of the reported urinary metabolites of nicotine are derived from cotinine. |
| FRCD ID | F05158 |
| CAS Number | 486-56-6 |
| PubChem CID | 408 |
| Formula | C10H12N2O |
| IUPAC Name | 1-methyl-5-pyridin-3-ylpyrrolidin-2-one |
| InChI Key | UIKROCXWUNQSPJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3 |
| Canonical SMILES | CN1C(CCC1=O)C2=CN=CC=C2 |
| Isomeric SMILES | CN1C(CCC1=O)C2=CN=CC=C2 |
| Wikipedia | Cotinine |
| Synonyms |
1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
rac Cotinine
15569-85-4
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-
rac-Cotinine
S-(-)-Cotinine
(S)-Cotinine
CHEMBL664
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)-
1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyrrolidinylpyridines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolidinylpyridines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyrrolidinylpyridine - Alkaloid or derivatives - Pyrrolidone - 2-pyrrolidone - N-alkylpyrrolidine - Pyrrolidine - Tertiary carboxylic acid amide - Heteroaromatic compound - Lactam - Carboxamide group - Carboxylic acid derivative - Azacycle - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 176.219 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 205 |
| Monoisotopic Mass | 176.095 |
| Exact Mass | 176.095 |
| XLogP | -0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9845 |
| Human Intestinal Absorption | HIA+ | 0.9913 |
| Caco-2 Permeability | Caco2+ | 0.7612 |
| P-glycoprotein Substrate | Non-substrate | 0.7711 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7427 |
| Non-inhibitor | 0.9538 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5483 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7328 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7327 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.5931 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9099 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9169 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8746 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9810 |
| Non-inhibitor | 0.9133 | |
| AMES Toxicity | Non AMES toxic | 0.9672 |
| Carcinogens | Non-carcinogens | 0.9572 |
| Fish Toxicity | Low FHMT | 0.8584 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8274 |
| Honey Bee Toxicity | Low HBT | 0.8669 |
| Biodegradation | Not ready biodegradable | 0.9224 |
| Acute Oral Toxicity | III | 0.5619 |
| Carcinogenicity (Three-class) | Non-required | 0.6720 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.0015 | LogS |
| Caco-2 Permeability | 1.2947 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4452 | LD50, mol/kg |
| Fish Toxicity | 1.8829 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1004 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Detoxification and elimination of nicotine by nectar-feeding birds. | J Comp Physiol B | 2017 May | 28150179 |
| A Biologically-Based Computational Approach to Drug Repurposing for Anthrax Infection. | Toxins (Basel) | 2017 Mar 10 | 28287432 |
| Breast Milk and Hair Testing to Detect Illegal Drugs, Nicotine, and Caffeine in Donors to a Human Milk Bank. | J Hum Lact | 2016 Aug | 27197576 |
| Tobacco smoking-response genes in blood and buccal cells. | Toxicol Lett | 2015 Jan 22 | 25447457 |
| Biomarkers of exposure among U.S. cigar smokers: an analysis of 1999-2012 National Health and Nutrition Examination Survey (NHANES) data. | Cancer Epidemiol Biomarkers Prev | 2014 Dec | 25380733 |
| Development of an experimental model for assessing the effects of cigarette smoke and virus infections on inflammatory responses to bacterial antigens. | Innate Immun | 2014 Aug | 24137042 |
| Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field. | Sci Total Environ | 2009 Aug 1 | 19464726 |
| The influence of gender, race, and menthol content on tobacco exposure measures. | Nicotine Tob Res | 2005 Aug | 16085529 |
| Smoking reduction promotes smoking cessation: results from a double blind, randomized, placebo-controlled trial of nicotine gum with 2-year follow-up. | Addiction | 2003 Oct | 14519176 |
| Optimization study for the reversed-phase ion-pair liquid chromatographic determination of nicotine in commercial tobacco products. | J Chromatogr A | 1999 Aug 13 | 10481983 |
| Nicotine gum dose and weight gain after smoking cessation. | J Consult Clin Psychol | 1996 Aug | 8803371 |
| Nontobacco sources of cotinine in the urine of nonsmokers. | Clin Pharmacol Ther | 1995 Apr | 7712678 |
| Smokeless tobacco abstinence effects and nicotine gum dose. | Psychopharmacology (Berl) | 1992 | 1738794 |
Targets
- General Function:
- Toxic substance binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
- Gene Name:
- CHRNA7
- Uniprot ID:
- P36544
- Molecular Weight:
- 56448.925 Da
References
- Briggs CA, McKenna DG, Monteggia LM, Touma E, Roch JM, Arneric SP, Gopalakrishnan M, Sullivan JP: Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant. Eur J Pharmacol. 1999 Feb 5;366(2-3):301-8. [10082212 ]