| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:30:30 UTC |
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| Updated at | 2022-05-11 16:30:30 UTC |
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| NP-MRD ID | NP0086770 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Hydroxycotinine |
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| Description | Hydroxycotinine belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. It is also excreted as a glucuronide conjugate (3HC-Gluc). Hydroxycotinine is a strong basic compound (based on its pKa). Hydroxycotinine can be biosynthesized from cotinine through its interaction with the enzyme cytochrome P450 2A6. In humans, hydroxycotinine is involved in nicotine metabolism pathway. Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. Quantitatively, the most important metabolite of nicotine in most mammalian species is cotinine. Hydroxycotinine was first documented in 1993 (PMID: 8468378). 3HC and 3HC-Gluc account for 40-60% of the nicotine dose in urine (PMID: 10080645) (PMID: 12194923) (PMID: 10585349) (PMID: 16765148). |
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| Structure | CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1 InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1 |
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| Synonyms | | Value | Source |
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| (3R-trans)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone | HMDB | | 3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone | HMDB | | 3-Hydroxycotinine | HMDB | | trans-3'-Hydroxycotinine | HMDB | | trans-3-Hydroxycotinine | HMDB | | 1-Methyl-3-hydroxy-5-(3-pyridyl)-2-pyrrolidinone | HMDB | | 3'-Hydroxycotinine | HMDB |
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| Chemical Formula | C10H12N2O2 |
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| Average Mass | 192.2145 Da |
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| Monoisotopic Mass | 192.08988 Da |
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| IUPAC Name | (5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one |
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| Traditional Name | hydroxycotinine |
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| CAS Registry Number | Not Available |
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| SMILES | CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1 |
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| InChI Identifier | InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1 |
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| InChI Key | XOKCJXZZNAUIQN-IENPIDJESA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pyridines and derivatives |
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| Sub Class | Pyrrolidinylpyridines |
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| Direct Parent | Pyrrolidinylpyridines |
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| Alternative Parents | |
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| Substituents | - Pyrrolidinylpyridine
- Alkaloid or derivatives
- Pyrrolidone
- 2-pyrrolidone
- N-alkylpyrrolidine
- Pyrrolidine
- Tertiary carboxylic acid amide
- Heteroaromatic compound
- Carboxamide group
- Lactam
- Secondary alcohol
- Carboxylic acid derivative
- Azacycle
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Bentley MC, Abrar M, Kelk M, Cook J, Phillips K: Validation of an assay for the determination of cotinine and 3-hydroxycotinine in human saliva using automated solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. J Chromatogr B Biomed Sci Appl. 1999 Feb 19;723(1-2):185-94. [PubMed:10080645 ]
- Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]
- Pacifici R, Pichini S, Altieri I, Rosa M, Bacosi A, Caronna A, Zuccaro P: Determination of nicotine and two major metabolites in serum by solid-phase extraction and high-performance liquid chromatography, and high-performance liquid chromatography-particle beam mass spectrometry. J Chromatogr. 1993 Feb 26;612(2):209-13. doi: 10.1016/0378-4347(93)80165-z. [PubMed:8468378 ]
- Tuomi T, Johnsson T, Reijula K: Analysis of nicotine, 3-hydroxycotinine, cotinine, and caffeine in urine of passive smokers by HPLC-tandem mass spectrometry. Clin Chem. 1999 Dec;45(12):2164-72. [PubMed:10585349 ]
- Lerman C, Tyndale R, Patterson F, Wileyto EP, Shields PG, Pinto A, Benowitz N: Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. Clin Pharmacol Ther. 2006 Jun;79(6):600-8. doi: 10.1016/j.clpt.2006.02.006. Epub 2006 May 11. [PubMed:16765148 ]
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