Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2021-09-14 15:45:00 UTC |
---|
HMDB ID | HMDB0001390 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Hydroxycotinine |
---|
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. 3HC and 3HC-Gluc account for 40-60% of the nicotine dose in urine. |
---|
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 |
---|
Synonyms | Value | Source |
---|
(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 |
|
---|
Chemical Formula | C10H12N2O2 |
---|
Average Molecular Weight | 192.2145 |
---|
Monoisotopic Molecular Weight | 192.089877638 |
---|
IUPAC Name | (5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one |
---|
Traditional Name | hydroxycotinine |
---|
CAS Registry Number | 34834-67-8 |
---|
SMILES | CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1 |
---|
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 |
---|
InChI Key | XOKCJXZZNAUIQN-IENPIDJESA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Pyridines and derivatives |
---|
Sub Class | Pyrrolidinylpyridines |
---|
Direct Parent | Pyrrolidinylpyridines |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -1.45 | LI,NY & GORROD,JW (1992) |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxycotinine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0kgy-3900000000-f4341e07a5c7a80b7536 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxycotinine GC-MS (1 TMS) - 70eV, Positive | splash10-0kmv-7920000000-c5ea44b12e63e343fb9a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxycotinine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 0V, Positive-QTOF | splash10-0006-0900000000-eb516ddd256ff613e87d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 30V, Positive-QTOF | splash10-053r-9300000000-f280be49213ae3a13079 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 0V, Positive-QTOF | splash10-0006-0900000000-7bda1053fba136e84796 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF | splash10-0006-0900000000-1c333f7a47d4c50ba147 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 30V, Positive-QTOF | splash10-001i-9200000000-764ed8e56080570ebb2b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF | splash10-000l-2900000000-bb4782c424b825499da9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF | splash10-0006-0900000000-e71a8aefcc63f8da573f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Positive-QTOF | splash10-002f-0900000000-9c8836e76f228880b9ef | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Positive-QTOF | splash10-0006-9700000000-ac3865df5f81a068cc89 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Negative-QTOF | splash10-0006-0900000000-422cb094c7d4df4e9032 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Negative-QTOF | splash10-0006-1900000000-455cd9052e09eb5156d2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Negative-QTOF | splash10-004i-9800000000-dbdfb504e7cdb984dc83 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF | splash10-0006-0900000000-0827985d284ee4847587 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Positive-QTOF | splash10-002f-0900000000-b7907c9e2b16530e9636 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Positive-QTOF | splash10-0a5c-5900000000-aeeff361755465a46a0a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Negative-QTOF | splash10-0006-0900000000-0bb6b33191167fa82f57 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Negative-QTOF | splash10-0fi3-3900000000-94e7e72f592f380dfd37 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Negative-QTOF | splash10-0ufr-8900000000-343920275b5ee98bf6ac | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | - Cytoplasm (predicted from logP)
|
---|
Biospecimen Locations | |
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.25 +/- 0.045 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | <1.00 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.35 +/- 0.15 uM | Adult (>18 years old) | Both | Smoking | | details | Blood | Detected and Quantified | 1.5 (0.52-2.6) uM | Adult (>18 years old) | Both | Active tobacco user | | details | Urine | Detected and Quantified | 4.5 (1.0-8.5) umol/mmol creatinine | Adult (>18 years old) | Both | Active tobacco user | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Smoking |
---|
- Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
- 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 ]
|
|
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB022597 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 8395266 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | 6210 |
---|
PubChem Compound | 10219774 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | MDB00000320 |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Jacob, Peyton, III; Shulgin, Alexander T.; Benowitz, Neal L. Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective. J. Med. Chem. (1990), 33 (7), pp 1888–1891 |
---|
Material Safety Data Sheet (MSDS) | Download (PDF) |
---|
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 ]
- Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033 ]
- Kim I, Huestis MA: A validated method for the determination of nicotine, cotinine, trans-3'-hydroxycotinine, and norcotinine in human plasma using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. J Mass Spectrom. 2006 Jun;41(6):815-21. [PubMed:16705667 ]
- 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. [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. Epub 2006 May 11. [PubMed:16765148 ]
|
---|