Hydroxycotinine (BioDeep_00000017846)
Secondary id: BioDeep_00000408585
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
(5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
化学式: C10H12N2O2 (192.0898732)
中文名称: 3-羟基可替宁
谱图信息:
最多检出来源 Homo sapiens(blood) 2.06%
Reviewed
Last reviewed on 2024-10-28.
Cite this Page
Hydroxycotinine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/hydroxycotinine (retrieved
2024-11-08) (BioDeep RN: BioDeep_00000017846). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CN1C(=O)C(O)CC1c1cccnc1
InChI: 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
描述信息
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. 3-Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. It is also excreted as a glucuronide conjugate (3HC-Gluc). 3HC and 3HC-Gluc account for 40-60\\\% of the nicotine dose in urine. [HMDB]
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. 3-Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. It is also excreted as a glucuronide conjugate (3HC-Gluc). 3HC and 3HC-Gluc account for 40-60\\\% of the nicotine dose in urine.
Hydroxycotinine is the main nicotine metabolite detected in smokers urine.
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:189719
- PubChem: 10219774
- PubChem: 414
- HMDB: HMDB0001390
- foodb: FDB022597
- chemspider: 8395266
- CAS: 34834-67-8
- PMhub: MS000000593
- medchemexpress: HY-113239
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
4 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(2)
- Nicotine Action Pathway:
Nicotine ⟶ Nornicotine - Nicotine Metabolism Pathway:
Nicotine ⟶ Nornicotine
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
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Clinica chimica acta; international journal of clinical chemistry.
2012 Jun; 413(11-12):978-84. doi:
10.1016/j.cca.2012.02.017. [PMID: 22394455] - Matthew J Binnington, Andy Z X Zhu, Caroline C Renner, Anne P Lanier, Dorothy K Hatsukami, Neal L Benowitz, Rachel F Tyndale. CYP2A6 and CYP2B6 genetic variation and its association with nicotine metabolism in South Western Alaska Native people.
Pharmacogenetics and genomics.
2012 Jun; 22(6):429-40. doi:
10.1097/fpc.0b013e3283527c1c. [PMID: 22569203] - Gideon St Helen, Maciej L Goniewicz, Delia Dempsey, Margaret Wilson, Peyton Jacob, Neal L Benowitz. Exposure and kinetics of polycyclic aromatic hydrocarbons (PAHs) in cigarette smokers.
Chemical research in toxicology.
2012 Apr; 25(4):952-64. doi:
10.1021/tx300043k. [PMID: 22428611] - Gang Chen, Nino E Giambrone, Philip Lazarus. Glucuronidation of trans-3'-hydroxycotinine by UGT2B17 and UGT2B10.
Pharmacogenetics and genomics.
2012 Mar; 22(3):183-90. doi:
10.1097/fpc.0b013e32834ff3a5. [PMID: 22228205] - François Marclay, Elia Grata, Laurent Perrenoud, Martial Saugy. A one-year monitoring of nicotine use in sport: frontier between potential performance enhancement and addiction issues.
Forensic science international.
2011 Dec; 213(1-3):73-84. doi:
10.1016/j.forsciint.2011.05.026. [PMID: 21719221] - Maria Dobrinas, Eva Choong, Muriel Noetzli, Jacques Cornuz, Nicolas Ansermot, Chin B Eap. Quantification of nicotine, cotinine, trans-3'-hydroxycotinine and varenicline in human plasma by a sensitive and specific UPLC-tandem mass-spectrometry procedure for a clinical study on smoking cessation.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Nov; 879(30):3574-82. doi:
10.1016/j.jchromb.2011.09.046. [PMID: 22014744] - Peyton Jacob, Lisa Yu, Minjiang Duan, Lita Ramos, Olivia Yturralde, Neal L Benowitz. Determination of the nicotine metabolites cotinine and trans-3'-hydroxycotinine in biologic fluids of smokers and non-smokers using liquid chromatography-tandem mass spectrometry: biomarkers for tobacco smoke exposure and for phenotyping cytochrome P450 2A6 activity.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Feb; 879(3-4):267-76. doi:
10.1016/j.jchromb.2010.12.012. [PMID: 21208832] - Andrew A Strasser, Neal L Benowitz, Angela G Pinto, Kathy Z Tang, Stephen S Hecht, Steve G Carmella, Rachel F Tyndale, Caryn E Lerman. Nicotine metabolite ratio predicts smoking topography and carcinogen biomarker level.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2011 Feb; 20(2):234-8. doi:
10.1158/1055-9965.epi-10-0674. [PMID: 21212060] - S Jean Hsieh, Lorraine B Ware, Mark D Eisner, Lisa Yu, Peyton Jacob, Christopher Havel, Maciej L Goniewicz, Michael A Matthay, Neal L Benowitz, Carolyn S Calfee. Biomarkers increase detection of active smoking and secondhand smoke exposure in critically ill patients.
Critical care medicine.
2011 Jan; 39(1):40-5. doi:
10.1097/ccm.0b013e3181fa4196. [PMID: 20935560] - Quan Gan, Wei Lu, Jiying Xu, Xinjian Li, Maciej Goniewicz, Neal L Benowitz, Stanton A Glantz. Chinese 'low-tar' cigarettes do not deliver lower levels of nicotine and carcinogens.
Tobacco control.
2010 Oct; 19(5):374-9. doi:
10.1136/tc.2009.033092. [PMID: 20507920] - Noel J Aquilina, Juana Mari Delgado-Saborit, Claire Meddings, Stephen Baker, Roy M Harrison, Peyton Jacob, Margaret Wilson, Lisa Yu, Minjiang Duan, Neal L Benowitz. Environmental and biological monitoring of exposures to PAHs and ETS in the general population.
Environment international.
2010 Oct; 36(7):763-71. doi:
10.1016/j.envint.2010.05.015. [PMID: 20591483] - Joe M Braun, Julie L Daniels, Charles Poole, Andrew F Olshan, Richard Hornung, John T Bernert, Yang Xia, Cynthia Bearer, Dana Boyd Barr, Bruce P Lanphear. A prospective cohort study of biomarkers of prenatal tobacco smoke exposure: the correlation between serum and meconium and their association with infant birth weight.
Environmental health : a global access science source.
2010 Aug; 9(?):53. doi:
10.1186/1476-069x-9-53. [PMID: 20799929] - Teresa R Gray, Rina D Eiden, Kenneth E Leonard, Gerard Connors, Shannon Shisler, Marilyn A Huestis. Nicotine and metabolites in meconium as evidence of maternal cigarette smoking during pregnancy and predictors of neonatal growth deficits.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2010 Jun; 12(6):658-64. doi:
10.1093/ntr/ntq068. [PMID: 20427459] - Neal L Benowitz, Katherine M Dains, Delia Dempsey, Lisa Yu, Peyton Jacob. Estimation of nicotine dose after low-level exposure using plasma and urine nicotine metabolites.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2010 May; 19(5):1160-6. doi:
10.1158/1055-9965.epi-09-1303. [PMID: 20447913] - E Köhler, S Avenarius, A Rabsilber, C Gerloff, G Jorch. Nicotine and its metabolites in amniotic fluid at birth--assessment of prenatal tobacco smoke exposure.
Human & experimental toxicology.
2010 May; 29(5):385-91. doi:
10.1177/0960327110363326. [PMID: 20164157] - Ki Young Kim, Young-Joo Lee, Bong Chul Chung, Jongki Hong, Byung Hwa Jung. Relations between toxicity and altered tissue distribution and urinary excretion of nicotine, cotinine, and hydroxycotinine after chronic oral administration of nicotine in rats.
Drug and chemical toxicology.
2010 Apr; 33(2):166-72. doi:
10.3109/01480540903196832. [PMID: 20307143] - Bingfang Yue, Mark M Kushnir, Francis M Urry, Alan L Rockwood. Quantitation of nicotine, its metabolites, and other related alkaloids in urine, serum, and plasma using LC-MS-MS.
Methods in molecular biology (Clifton, N.J.).
2010; 603(?):389-98. doi:
10.1007/978-1-60761-459-3_38. [PMID: 20077091] - Rafał Rudzińiski. [Effect of tobacco smoking on the course and degree of advancement inflammation in periodontal tissue].
Annales Academiae Medicae Stetinensis.
2010; 56(2):97-105. doi:
NULL. [PMID: 21469287] - Diaa M Shakleya, Marilyn A Huestis. Simultaneous and sensitive measurement of nicotine, cotinine, trans-3'-hydroxycotinine and norcotinine in human plasma by liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Nov; 877(29):3537-42. doi:
10.1016/j.jchromb.2009.08.033. [PMID: 19748838] - M K Ho, J C Mwenifumbo, N Al Koudsi, K S Okuyemi, J S Ahluwalia, N L Benowitz, R F Tyndale. Association of nicotine metabolite ratio and CYP2A6 genotype with smoking cessation treatment in African-American light smokers.
Clinical pharmacology and therapeutics.
2009 Jun; 85(6):635-43. doi:
10.1038/clpt.2009.19. [PMID: 19279561] - Gary E Swan, Christina N Lessov-Schlaggar, Andrew W Bergen, Yungang He, Rachel F Tyndale, Neal L Benowitz. Genetic and environmental influences on the ratio of 3'hydroxycotinine to cotinine in plasma and urine.
Pharmacogenetics and genomics.
2009 May; 19(5):388-98. doi:
10.1097/fpc.0b013e32832a404f. [PMID: 19300303] - Wojciech Piekoszewski, Ewa Florek, Maksymilian Kulza, Jolanta Wilimowska, Urszula Loba. [Development of analytical method for determination nicotine metabolites in urine].
Przeglad lekarski.
2009; 66(10):593-7. doi:
NULL. [PMID: 20301889] - Liza U Ljungberg, Karin Persson. Effect of nicotine and nicotine metabolites on angiotensin-converting enzyme in human endothelial cells.
Endothelium : journal of endothelial cell research.
2008 Sep; 15(5-6):239-45. doi:
10.1080/10623320802487627. [PMID: 19065315] - Hideaki Matsuki, Keiji Hashimoto, Keiichi Arashidani, Yukio Akiyama, Takashi Amagai, Yoshiaki Ishizu, Hidetsuru Matsushita. Studies on a simultaneous analytical method of urinary nicotine and its metabolites, and their half-lives in urine.
Journal of UOEH.
2008 Sep; 30(3):235-52. doi:
10.7888/juoeh.30.235. [PMID: 18783007] - Marc E Mooney, Zhong-Ze Li, Sharon E Murphy, Paul R Pentel, Chap Le, Dorothy K Hatsukami. Stability of the nicotine metabolite ratio in ad libitum and reducing smokers.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Jun; 17(6):1396-400. doi:
10.1158/1055-9965.epi-08-0242. [PMID: 18559554] - J C Mwenifumbo, C N Lessov-Schlaggar, Q Zhou, R E Krasnow, G E Swan, N L Benowitz, R F Tyndale. Identification of novel CYP2A6*1B variants: the CYP2A6*1B allele is associated with faster in vivo nicotine metabolism.
Clinical pharmacology and therapeutics.
2008 Jan; 83(1):115-21. doi:
10.1038/sj.clpt.6100246. [PMID: 17522595] - Eduardo Lazcano-Ponce, Neal Benowitz, Luisa Maria Sanchez-Zamorano, Larissa Barbosa-Sanchez, Raydel Valdes-Salgado, Peyton Jacob, Rodrigo Diaz, Mauricio Hernandez-Avila. Secondhand smoke exposure in Mexican discotheques.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2007 Oct; 9(10):1021-6. doi:
10.1080/14622200701495967. [PMID: 17852765] - Shixia Feng, Sunil Kapur, Mohamadi Sarkar, Raheema Muhammad, Paul Mendes, Kirk Newland, Hans J Roethig. Respiratory retention of nicotine and urinary excretion of nicotine and its five major metabolites in adult male smokers.
Toxicology letters.
2007 Sep; 173(2):101-6. doi:
10.1016/j.toxlet.2007.06.016. [PMID: 17716838] - Anna M Lee, Christopher Jepson, Peter G Shields, Neal Benowitz, Caryn Lerman, Rachel F Tyndale. CYP2B6 genotype does not alter nicotine metabolism, plasma levels, or abstinence with nicotine replacement therapy.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Jun; 16(6):1312-4. doi:
10.1158/1055-9965.epi-07-0188. [PMID: 17548706] - E Köhler, S Avenarius, A Rabsilber, C Gerloff, G Jorch. Assessment of prenatal tobacco smoke exposure by determining nicotine and its metabolites in meconium.
Human & experimental toxicology.
2007 Jun; 26(6):535-44. doi:
10.1177/0960327107072391. [PMID: 17698949] - Denise B Kandel, Mei-Chen Hu, Christine Schaffran, J Richard Udry, Neal L Benowitz. Urine nicotine metabolites and smoking behavior in a multiracial/multiethnic national sample of young adults.
American journal of epidemiology.
2007 Apr; 165(8):901-10. doi:
10.1093/aje/kwm010. [PMID: 17322544] - Ivan Berlin, Maria J Gasior, Eric T Moolchan. Sex-based and hormonal contraception effects on the metabolism of nicotine among adolescent tobacco-dependent smokers.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2007 Apr; 9(4):493-8. doi:
10.1080/14622200701243193. [PMID: 17454704] - Micha Levi, Delia A Dempsey, Neal L Benowitz, Lewis B Sheiner. Population pharmacokinetics of nicotine and its metabolites I. Model development.
Journal of pharmacokinetics and pharmacodynamics.
2007 Feb; 34(1):5-21. doi:
10.1007/s10928-006-9027-z. [PMID: 17206524] - Hanna Kedziora, Ewa Florek, Wojciech Piekoszewski, Grzegorz H Breborowicz, Andrzej Anholcer, Ewa Gomółka, Maksymilian Kulza, Artur Stanek. [Concentration of cotinine and trans-3'-hydroxycotinine and its glucuronides in urine of smoking pregnant women].
Przeglad lekarski.
2007; 64(10):740-6. doi:
NULL. [PMID: 18409299] - F K St Charles, G R Krautter, M Dixon, D C Mariner. A comparison of nicotine dose estimates in smokers between filter analysis, salivary cotinine, and urinary excretion of nicotine metabolites.
Psychopharmacology.
2006 Dec; 189(3):345-54. doi:
10.1007/s00213-006-0586-x. [PMID: 17028908] - Janne Hukkanen, Peyton Jacob, Neal L Benowitz. Effect of grapefruit juice on cytochrome P450 2A6 and nicotine renal clearance.
Clinical pharmacology and therapeutics.
2006 Nov; 80(5):522-30. doi:
10.1016/j.clpt.2006.08.006. [PMID: 17112808] - Neal L Benowitz, Gary E Swan, Peyton Jacob, Christina N Lessov-Schlaggar, Rachel F Tyndale. CYP2A6 genotype and the metabolism and disposition kinetics of nicotine.
Clinical pharmacology and therapeutics.
2006 Nov; 80(5):457-67. doi:
10.1016/j.clpt.2006.08.011. [PMID: 17112802] - G E Matt, P J E Quintana, S Liles, M F Hovell, J M Zakarian, P Jacob, N L Benowitz. Evaluation of urinary trans-3'-hydroxycotinine as a biomarker of children's environmental tobacco smoke exposure.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2006 Nov; 11(6):507-23. doi:
10.1080/13547500600902458. [PMID: 17056471] - Viba Malaiyandi, Shari D Goodz, Edward M Sellers, Rachel F Tyndale. CYP2A6 genotype, phenotype, and the use of nicotine metabolites as biomarkers during ad libitum smoking.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2006 Oct; 15(10):1812-9. doi:
10.1158/1055-9965.epi-05-0723. [PMID: 17035386] - Yukio Akiyama, Keiichi Arashidani, Wakana Kawano, Naoki Kunugita. Urinary nicotine and its metabolites as a biomarker of exposure to environmental tobacco smoke.
Journal of UOEH.
2006 Sep; 28(3):245-52. doi:
10.7888/juoeh.28.245. [PMID: 16981401] - Insook Kim, Marilyn A Huestis. 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.
Journal of mass spectrometry : JMS.
2006 Jun; 41(6):815-21. doi:
10.1002/jms.1039. [PMID: 16705667] - Caryn Lerman, Rachel Tyndale, Freda Patterson, E Paul Wileyto, Peter G Shields, Angela Pinto, Neal Benowitz. Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation.
Clinical pharmacology and therapeutics.
2006 Jun; 79(6):600-8. doi:
10.1016/j.clpt.2006.02.006. [PMID: 16765148] - Krystyna Tyrpień, Tomasz Wielkoszyński, Małgorzata Kowalska, Grzegorz Mańka, Cezary Dobosz. [Assessment of occurrence frequency of cotinine and trans-3'-hydroxycotinine in chosen body fluid samples].
Przeglad lekarski.
2006; 63(10):897-9. doi:
NULL. [PMID: 17288179] - Jill M Williams, Douglas M Ziedonis, Francisca Abanyie, Marc L Steinberg, Jonathan Foulds, Neal L Benowitz. Increased nicotine and cotinine levels in smokers with schizophrenia and schizoaffective disorder is not a metabolic effect.
Schizophrenia research.
2005 Nov; 79(2-3):323-35. doi:
10.1016/j.schres.2005.04.016. [PMID: 15961287] - Hiroyuki Yamanaka, Miki Nakajima, Miki Katoh, Ayano Kanoh, Osamu Tamura, Hiroyuki Ishibashi, Tsuyoshi Yokoi. Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Jan; 33(1):23-30. doi:
10.1124/dmd.104.001701. [PMID: 15470160]