Nicotinuric acid (BioDeep_00000001394)
Secondary id: BioDeep_00000405551
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
化学式: C8H8N2O3 (180.0534898)
中文名称: N-烟酰甘氨酸, 酰基甘氨酸, 烟酰甘氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 0.44%
Last reviewed on 2024-09-13.
Cite this Page
Nicotinuric acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/nicotinuric_acid (retrieved
2024-11-22) (BioDeep RN: BioDeep_00000001394). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C1=CC(=CN=C1)C(=O)NCC(=O)O
InChI: InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)
描述信息
Nicotinuric acid is an acylglycine. Acylglycines are normally minor metabolites of fatty acids. However, the excretion of certain acylglycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acylglycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction acyl-CoA + glycine <-> CoA + N-acylglycine. Nicotinuric acid is the major detoxification product of nicotinic acid. It may serve as a simple quantitative index of hepatic biotransformation of nicotinic acid (PMID:3243933).
Nicotinuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:
Nicotinuric acid is an acyl glycine. Nicotinuric acid is a metabolite of nicotinic acid.
同义名列表
20 个代谢物同义名
2-[(pyridin-3-yl)formamido]acetic acid; N-(3-Pyridinylcarbonyl)-(9ci)-glycine; Nicotinuric acid, monosodium salt; N-(3-Pyridinylcarbonyl)-glycine; N-(Pyridin-3-ylcarbonyl)glycine; N-Nicotinoyl-(8ci)-glycine; N-nicotinoyl-Glycine; N-Nicotinuric acid; Nicotinoyl-glycine; N-Nicotinylglycine; Nicotinoylglycine; Nicotinuric acid; Nicotinylglycine; Nicotinic acid; N-Nicotinurate; Nicotinurate; nicotinate; Nicotinuric acid; Nicotinurate; Nicotinuric acid
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:7563
- KEGG: C05380
- PubChem: 68499
- HMDB: HMDB0003269
- Metlin: METLIN1499
- ChEMBL: CHEMBL458725
- Wikipedia: Niacin
- foodb: FDB023135
- chemspider: 61774
- CAS: 583-08-4
- PMhub: MS000000439
- PubChem: 7754
- 3DMET: B00772
- NIKKAJI: J11.524J
- RefMet: Nicotinuric acid
- medchemexpress: HY-113353
- KNApSAcK: 7563
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 8187 - Lates calcarifer: 10.3389/FPHYS.2020.00205
- 1822464 - Paraburkholderia: 10.1128/AEM.01851-20
- 569774 - 金线莲: -
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
- Jonathan Isaak Kremer, Katharina Gömpel, Tamara Bakuradze, Gerhard Eisenbrand, Elke Richling. Urinary Excretion of Niacin Metabolites in Humans After Coffee Consumption.
Molecular nutrition & food research.
2018 04; 62(7):e1700735. doi:
10.1002/mnfr.201700735
. [PMID: 29468817] - Sergio Montserrat-de la Paz, M Carmen Naranjo, Sergio Lopez, Rocio Abia, Francisco J Garcia Muriana, Beatriz Bermudez. Niacin and its metabolites as master regulators of macrophage activation.
The Journal of nutritional biochemistry.
2017 01; 39(?):40-47. doi:
10.1016/j.jnutbio.2016.09.008
. [PMID: 27771381] - Filippos Kesisoglou, Stefaan Rossenu, Colm Farrell, Michiel Van Den Heuvel, Marita Prohn, Shaun Fitzpatrick, Pieter-Jan De Kam, Ryan Vargo. Development of in vitro-in vivo correlation for extended-release niacin after administration of hypromellose-based matrix formulations to healthy volunteers.
Journal of pharmaceutical sciences.
2014 Nov; 103(11):3713-3723. doi:
10.1002/jps.24179
. [PMID: 25256703] - Chun-Feng Huang, Mei-Ling Cheng, Chun-Ming Fan, Chuang-Ye Hong, Ming-Shi Shiao. Nicotinuric acid: a potential marker of metabolic syndrome through a metabolomics-based approach.
Diabetes care.
2013 Jun; 36(6):1729-31. doi:
10.2337/dc12-1067
. [PMID: 23275373] - Alastair B Ross, Emma Pere-Trépat, Ivan Montoliu, Francois-Pierre J Martin, Sebastiano Collino, Sofia Moco, Jean-Philippe Godin, Marilyn Cléroux, Philippe A Guy, Isabelle Breton, Rodrigo Bibiloni, Anita Thorimbert, Isabelle Tavazzi, Lionel Tornier, Aude Bebuis, Stephen J Bruce, Maurice Beaumont, Laurent-Bernard Fay, Sunil Kochhar. A whole-grain-rich diet reduces urinary excretion of markers of protein catabolism and gut microbiota metabolism in healthy men after one week.
The Journal of nutrition.
2013 Jun; 143(6):766-73. doi:
10.3945/jn.112.172197
. [PMID: 23616503] - Man Liu, Dan Zhang, Xiaolin Wang, Lina Zhang, Jing Han, Man Yang, Xue Xiao, Yanan Zhang, Huichen Liu. Simultaneous quantification of niacin and its three main metabolites in human plasma by LC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2012 Sep; 904(?):107-14. doi:
10.1016/j.jchromb.2012.07.030
. [PMID: 22884475] - Yang Sun, Zeqin Lian, Chunying Jiang, Yinghong Wang, Haibo Zhu. Beneficial metabolic effects of 2',3',5'-tri-acetyl-N6- (3-hydroxylaniline) adenosine in the liver and plasma of hyperlipidemic hamsters.
PloS one.
2012; 7(3):e32115. doi:
10.1371/journal.pone.0032115
. [PMID: 22470419] - Jia V Li, Jasmina Saric, Yulan Wang, Jennifer Keiser, Jürg Utzinger, Elaine Holmes. Chemometric analysis of biofluids from mice experimentally infected with Schistosoma mansoni.
Parasites & vectors.
2011 Sep; 4(?):179. doi:
10.1186/1756-3305-4-179
. [PMID: 21929782] - Teddy Kosoglou, Yali Zhu, Paul Statkevich, Ilias Triantafyllou, William Taggart, Fengjuan Xuan, Kenneth T Kim, David L Cutler. Assessment of potential pharmacokinetic interactions of ezetimibe/simvastatin and extended-release niacin tablets in healthy subjects.
European journal of clinical pharmacology.
2011 May; 67(5):483-92. doi:
10.1007/s00228-010-0955-6
. [PMID: 21120461] - Christine Ahlström, Lambertus A Peletier, Rasmus Jansson-Löfmark, Johan Gabrielsson. Feedback modeling of non-esterified fatty acids in rats after nicotinic acid infusions.
Journal of pharmacokinetics and pharmacodynamics.
2011 Feb; 38(1):1-24. doi:
10.1007/s10928-010-9172-2
. [PMID: 21046209] - Ines Reiche, Sabine Westphal, Jens Martens-Lobenhoffer, Uwe Tröger, Claus Luley, Stefanie M Bode-Böger. Pharmacokinetics and dose recommendations of Niaspan® in chronic kidney disease and dialysis patients.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2011 Jan; 26(1):276-82. doi:
10.1093/ndt/gfq344
. [PMID: 20562093] - Lei Wang, Yong-ping Qin, Xiao-li Gong, Feng Nan, Jin Xiang, Qin Yu, Mao-zhi Liang. [Determination of nicacid and its metabolites in human plasma by HPLC-MS/MS].
Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition.
2010 Nov; 41(6):1051-4. doi:
. [PMID: 21265114]
- Jaswanth Kumar Inamadugu, Rajasekhar Damaramadugu, Ramesh Mullangi, Venkateswarlu Ponneri. Simultaneous determination of niacin and its metabolites--nicotinamide, nicotinuric acid and N-methyl-2-pyridone-5-carboxamide--in human plasma by LC-MS/MS and its application to a human pharmacokinetic study.
Biomedical chromatography : BMC.
2010 Oct; 24(10):1059-74. doi:
10.1002/bmc.1406
. [PMID: 20853461] - Devita Surjana, Gary M Halliday, Diona L Damian. Role of nicotinamide in DNA damage, mutagenesis, and DNA repair.
Journal of nucleic acids.
2010 Jul; 2010(?):. doi:
10.4061/2010/157591
. [PMID: 20725615] - B Lauring, K Rosko, W-L Luo, L Wenning, J Kissling, K Roupe, J F Paolini, J Wagner, E Lai. A comparison of the pharmacokinetics of two different formulations of extended-release niacin.
Current medical research and opinion.
2009 Jan; 25(1):15-22. doi:
10.1185/03007990802569034
. [PMID: 19210135] - Anbu Pandian, Anjali Arora, Laurence S Sperling, Bobby V Khan. Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin.
Vascular health and risk management.
2008; 4(5):1001-9. doi:
10.2147/vhrm.s3460
. [PMID: 19183748] - Eleni Skordi, Ivan K S Yap, Sandrine P Claus, François-Pierre J Martin, Olivier Cloarec, Johan Lindberg, Ina Schuppe-Koistinen, Elaine Holmes, Jeremy K Nicholson. Analysis of time-related metabolic fluctuations induced by ethionine in the rat.
Journal of proteome research.
2007 Dec; 6(12):4572-81. doi:
10.1021/pr070268q
. [PMID: 17966971] - R Menon, D Tolbert, E Cefali. The comparative bioavailability of an extended-release niacin and lovastatin fixed dose combination tablet versus extended-release niacin tablet, lovastatin tablet and a combination of extended-release niacin tablet and lovastatin tablet.
Biopharmaceutics & drug disposition.
2007 Sep; 28(6):297-306. doi:
10.1002/bdd.555
. [PMID: 17571283] - R M Menon, M H Adams, M A González, D S Tolbert, J H Leu, E A Cefali. Plasma and urine pharmacokinetics of niacin and its metabolites from an extended-release niacin formulation.
International journal of clinical pharmacology and therapeutics.
2007 Aug; 45(8):448-54. doi:
10.5414/cpp45448
. [PMID: 17725178] - C Daniel Meyers, Paul Liu, Vaijinath S Kamanna, Moti L Kashyap. Nicotinic acid induces secretion of prostaglandin D2 in human macrophages: an in vitro model of the niacin flush.
Atherosclerosis.
2007 Jun; 192(2):253-8. doi:
10.1016/j.atherosclerosis.2006.07.014
. [PMID: 16945375] - Rajeev M Menon, Mario A González, Marijke H Adams, Dwain S Tolbert, Jocelyn H Leu, Eugenio A Cefali. Effect of the rate of niacin administration on the plasma and urine pharmacokinetics of niacin and its metabolites.
Journal of clinical pharmacology.
2007 Jun; 47(6):681-8. doi:
10.1177/0091270007300264
. [PMID: 17463214] - P Pfuhl, U Kärcher, N Häring, A Baumeister, Mona Abdel Tawab, M Schubert-Zsilavecz. Simultaneous determination of niacin, niacinamide and nicotinuric acid in human plasma.
Journal of pharmaceutical and biomedical analysis.
2005 Jan; 36(5):1045-52. doi:
10.1016/j.jpba.2004.08.033
. [PMID: 15620531] - Yunsheng Hsieh, Jiwen Chen. Simultaneous determination of nicotinic acid and its metabolites using hydrophilic interaction chromatography with tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2005; 19(21):3031-6. doi:
10.1002/rcm.2171
. [PMID: 16193536] - Tsutomu Fukuwatari, Hideko Wada, Ryuzo Sasaki, Katsumi Shibata. Effects of excess nicotinamide administration on the urinary excretion of nicotinamide N-oxide and nicotinuric acid by rats.
Bioscience, biotechnology, and biochemistry.
2004 Jan; 68(1):44-50. doi:
10.1271/bbb.68.44
. [PMID: 14745162] - M Iwaki, T Ogiso, H Hayashi, T Tanino, L Z Benet. Acute dose-dependent disposition studies of nicotinic acid in rats.
Drug metabolism and disposition: the biological fate of chemicals.
1996 Jul; 24(7):773-9. doi:
. [PMID: 8818575]
- M Iwaki, T Ogiso, H Hayashi, E T Lin, L Z Benet. Simultaneous measurement of nicotinic acid and its major metabolite, nicotinuric acid in urine using high-performance liquid chromatography: application of solid-liquid extraction.
Journal of chromatography. B, Biomedical applications.
1994 Nov; 661(1):154-8. doi:
10.1016/0378-4347(94)00332-7
. [PMID: 7866544] - Y Miyauchi, N Sano, T Nakamura. Simultaneous determination of nicotinic acid and its two metabolites in human plasma using solid-phase extraction in combination with high performance liquid chromatography.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
1993; 63(2):145-9. doi:
NULL
. [PMID: 8407165] - R H Stern, D Freeman, J D Spence. Differences in metabolism of time-release and unmodified nicotinic acid: explanation of the differences in hypolipidemic action?.
Metabolism: clinical and experimental.
1992 Aug; 41(8):879-81. doi:
10.1016/0026-0495(92)90170-f
. [PMID: 1640866] - R H Stern, J D Spence, D J Freeman, A Parbtani. Tolerance to nicotinic acid flushing.
Clinical pharmacology and therapeutics.
1991 Jul; 50(1):66-70. doi:
10.1038/clpt.1991.104
. [PMID: 1855354] - K Shibata, H Kakehi, H Matsuo. Niacin catabolism in rodents.
Journal of nutritional science and vitaminology.
1990 Apr; 36(2):87-98. doi:
10.3177/jnsv.36.87
. [PMID: 2143779] - R W Ding, K Kolbe, B Merz, J de Vries, E Weber, L Z Benet. Pharmacokinetics of nicotinic acid-salicylic acid interaction.
Clinical pharmacology and therapeutics.
1989 Dec; 46(6):642-7. doi:
10.1038/clpt.1989.200
. [PMID: 2598568] - H L Figge, J Figge, P F Souney, F M Sacks, L Shargel, J E Janosik, A F Kaul. Comparison of excretion of nicotinuric acid after ingestion of two controlled release nicotinic acid preparations in man.
Journal of clinical pharmacology.
1988 Dec; 28(12):1136-40. doi:
10.1002/j.1552-4604.1988.tb05731.x
. [PMID: 3243933] - K Takikawa, K Miyazaki, T Arita. High-performance liquid chromatographic determination of nicotinic acid and its metabolites, nicotinuric acid and nicotinamide, in plasma.
Journal of chromatography.
1982 Dec; 233(?):343-8. doi:
10.1016/s0378-4347(00)81765-x
. [PMID: 6219121] - N Hengen, V Seiberth, M Hengen. High-performance liquid-chromatographic determination of free nicotinic acid and its metabolite, nicotinuric acid, in plasma and urine.
Clinical chemistry.
1978 Oct; 24(10):1740-3. doi:
. [PMID: 699281]
- E M JONES, W H ELLIOTT. The synthesis of nicotinuric acid by rat-kidney preparations.
The Biochemical journal.
1959 Dec; 73(?):706-13. doi:
10.1042/bj0730706
. [PMID: 14407699] - K M JONES, W H ELLIOTT. The synthesis of nicotinuric acid by rat kidney mitochondria.
Biochimica et biophysica acta.
1954 Aug; 14(4):586-7. doi:
10.1016/0006-3002(54)90250-4
. [PMID: 13198927]