Pivalic acid (BioDeep_00000600486)
Volatile Flavor Compounds natural product
代谢物信息卡片
2,2-dimethyl-propanoic acid
化学式: C5H10O2 (102.068076)
中文名称: 三甲基乙酸(PA), 三甲基乙酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)(C)C(=O)O
InChI: InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
描述信息
A branched, short-chain fatty acid composed of propanoic acid having two methyl substituents at the 2-position.
同义名列表
3 个代谢物同义名
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:45133
- PubChem: 6417
- Metlin: METLIN4472
- ChEMBL: CHEMBL322719
- CAS: 75-98-9
- MetaboLights: MTBLC45133
- LOTUS: LTS0123133
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)
5 个相关的物种来源信息
- 2 - Bacteria: LTS0123133
- 1883 - Streptomyces: LTS0123133
- 33903 - Streptomyces avermitilis: 10.1111/J.1462-2920.2011.02465.X
- 33903 - Streptomyces avermitilis: LTS0123133
- 2062 - Streptomycetaceae: LTS0123133
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
- Kimitaka Nakazaki, Erika Ogawa, Mika Ishige, Nobuyuki Ishige, Tatsuo Fuchigami, Shori Takahashi. Hypocarnitinemia Observed in an Infant Treated with Short-Term Administration of Antibiotic Containing Pivalic Acid.
The Tohoku journal of experimental medicine.
2018 04; 244(4):279-282. doi:
10.1620/tjem.244.279. [PMID: 29628457] - Timothy H Witney, Federica Pisaneschi, Israt S Alam, Sebastian Trousil, Maciej Kaliszczak, Frazer Twyman, Diana Brickute, Quang-Dé Nguyen, Zachary Schug, Eyal Gottlieb, Eric O Aboagye. Preclinical evaluation of 3-18F-fluoro-2,2-dimethylpropionic acid as an imaging agent for tumor detection.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2014 Sep; 55(9):1506-12. doi:
10.2967/jnumed.114.140343. [PMID: 25012458] - James Q Del Rosso, Leon Kircik. A Comprehensive Review of Clocortolone Pivalate 0.1\% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses.
The Journal of clinical and aesthetic dermatology.
2012 Jul; 5(7):20-4. doi:
". [PMID: 22798972] - Karen K Y Lam, Xingji Zheng, Roberto Forestieri, Aruna D Balgi, Matt Nodwell, Sarah Vollett, Hilary J Anderson, Raymond J Andersen, Yossef Av-Gay, Michel Roberge. Nitazoxanide stimulates autophagy and inhibits mTORC1 signaling and intracellular proliferation of Mycobacterium tuberculosis.
PLoS pathogens.
2012; 8(5):e1002691. doi:
10.1371/journal.ppat.1002691. [PMID: 22589723] - Yoko Nakajima, Tetsuya Ito, Yasuhiro Maeda, Sayaka Ichiki, Naruji Sugiyama, Mihoko Mizuno, Yasuko Makino, Tokio Sugiura, Yukihisa Kurono, Hajime Togari. Detection of pivaloylcarnitine in pediatric patients with hypocarnitinemia after long-term administration of pivalate-containing antibiotics.
The Tohoku journal of experimental medicine.
2010 Aug; 221(4):309-13. doi:
10.1620/tjem.221.309. [PMID: 20651467] - Sriram Govindan, Emily J A Taylor, Colin W Taylor. Ca(2+) signalling by P2Y receptors in cultured rat aortic smooth muscle cells.
British journal of pharmacology.
2010 Aug; 160(8):1953-62. doi:
10.1111/j.1476-5381.2010.00763.x. [PMID: 20649593] - Andrew D Cox, Frank St Michael, Dhamodharan Neelamegan, Suzanne Lacelle, Chantelle Cairns, James C Richards. Investigating the candidacy of LPS-based glycoconjugates to prevent invasive meningococcal disease: chemical strategies to prepare glycoconjugates with good carbohydrate loading.
Glycoconjugate journal.
2010 May; 27(4):401-17. doi:
10.1007/s10719-010-9287-0. [PMID: 20340043] - Liliane Todesco, Michael Bodmer, Karin Vonwil, Daniel Häussinger, Stephan Krähenbühl. Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2.
Chemico-biological interactions.
2009 Aug; 180(3):472-7. doi:
10.1016/j.cbi.2009.02.014. [PMID: 19539806] - Kenneth A Jacobson, Andrei A Ivanov, Sonia de Castro, T Kendall Harden, Hyojin Ko. Development of selective agonists and antagonists of P2Y receptors.
Purinergic signalling.
2009 Mar; 5(1):75-89. doi:
10.1007/s11302-008-9106-2. [PMID: 18600475] - Tetsuya Ito. Children's toxicology from bench to bed--Liver injury (1): Drug-induced metabolic disturbance--toxicity of 5-FU for pyrimidine metabolic disorders and pivalic acid for carnitine metabolism.
The Journal of toxicological sciences.
2009; 34 Suppl 2(?):SP217-22. doi:
10.2131/jts.34.sp217. [PMID: 19571472] - Shuichi Ohnishi, Noboru Okamura, Shingo Sakamoto, Hiroshi Hasegawa, Ryo Norikura, Eri Kanaoka, Kouji Takahashi, Kazutoshi Horie, Kiyoshi Sakamoto, Takahiko Baba. Role of Na+/L-carnitine transporter (OCTN2) in renal handling of pivaloylcarnitine and valproylcarnitine formed during pivalic acid-containing prodrugs and valproic acid treatment.
Drug metabolism and pharmacokinetics.
2008; 23(4):293-303. doi:
10.2133/dmpk.23.293. [PMID: 18762717] - Jane Doberenz, Frank Hirche, Uta Keller, Klaus Eder. Pivalate lowers litter sizes and weights in female rats independent of its effect on carnitine status.
Reproductive toxicology (Elmsford, N.Y.).
2007 Jul; 24(1):83-8. doi:
10.1016/j.reprotox.2007.03.011. [PMID: 17482425] - Noboru Okamura, Shuichi Ohnishi, Hiroyuki Shimaoka, Ryo Norikura, Hiroshi Hasegawa. Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid.
Pharmaceutical research.
2006 Aug; 23(8):1729-35. doi:
10.1007/s11095-006-9002-9. [PMID: 16826461] - Toshiro Yamaguchi, Yoshitsugu Nakajima, Yutaka Nakamura. Possible mechanism for species difference on the toxicity of pivalic acid between dogs and rats.
Toxicology and applied pharmacology.
2006 Jul; 214(1):61-8. doi:
10.1016/j.taap.2005.11.013. [PMID: 16430936] - Tom L Broderick. Hypocarnitinaemia induced by sodium pivalate in the rat is associated with left ventricular dysfunction and impaired energy metabolism.
Drugs in R&D.
2006; 7(3):153-61. doi:
10.2165/00126839-200607030-00002. [PMID: 16752941] - Piyush Kumar, Steven A McQuarrie, Aihya Zhou, Alexander J B McEwan, Leonard I Wiebe. [131I]Iodoazomycin arabinoside for low-dose-rate isotope radiotherapy: radiolabeling, stability, long-term whole-body clearance and radiation dosimetry estimates in mice.
Nuclear medicine and biology.
2005 Aug; 32(6):647-53. doi:
10.1016/j.nucmedbio.2005.04.019. [PMID: 16026712] - Alan T Davis, Thomas J Monroe. Carnitine deficiency and supplementation do not affect the gene expression of carnitine biosynthetic enzymes in rats.
The Journal of nutrition.
2005 Apr; 135(4):761-4. doi:
10.1093/jn/135.4.761. [PMID: 15795431] - Charles A Stanley. Carnitine deficiency disorders in children.
Annals of the New York Academy of Sciences.
2004 Nov; 1033(?):42-51. doi:
10.1196/annals.1320.004. [PMID: 15591002] - Chunze Li, Mark P Grillo, Leslie Z Benet. In vitro studies on the chemical reactivity of 2,4-dichlorophenoxyacetyl-S-acyl-CoA thioester.
Toxicology and applied pharmacology.
2003 Mar; 187(2):101-9. doi:
10.1016/s0041-008x(02)00043-1. [PMID: 12649042] - Katrin Färber, Brigitte Schumann, Otto Miersch, Werner Roos. Selective desensitization of jasmonate- and pH-dependent signaling in the induction of benzophenanthridine biosynthesis in cells of Eschscholzia californica.
Phytochemistry.
2003 Feb; 62(3):491-500. doi:
10.1016/s0031-9422(02)00562-9. [PMID: 12620362] - Eric P Brass. Pivalate-generating prodrugs and carnitine homeostasis in man.
Pharmacological reviews.
2002 Dec; 54(4):589-98. doi:
10.1124/pr.54.4.589. [PMID: 12429869] - J H Niezen, W A G Charleston, H A Robertson, D Shelton, G C Waghorn, R Green. The effect of feeding sulla (Hedysarum coronarium) or lucerne (Medicago sativa) on lamb parasite burdens and development of immunity to gastrointestinal nematodes.
Veterinary parasitology.
2002 May; 105(3):229-45. doi:
10.1016/s0304-4017(02)00014-6. [PMID: 11934463] - R Ricciolini, M Scalibastri, P Carminati, A Arduini. The effect of pivalate treatment of pregnant rats on body mass and insulin levels in the adult offspring.
Life sciences.
2001 Aug; 69(15):1733-8. doi:
10.1016/s0024-3205(01)01254-1. [PMID: 11665835] - N Okudaira, M Fujigaki, T Nakayoshi, I Komiya, Y Sugiyama. Up-regulation of carnitine transporters helps maintain tissue carnitine levels in carnitine deficiency induced by pivalic acid.
Pharmaceutical research.
2001 Apr; 18(4):439-45. doi:
10.1023/a:1011042008169. [PMID: 11451029] - E Arrigoni-Martelli, V Caso. Carnitine protects mitochondria and removes toxic acyls from xenobiotics.
Drugs under experimental and clinical research.
2001; 27(1):27-49. doi:
NULL. [PMID: 11276827] - R Ohashi, I Tamai, H Yabuuchi, J I Nezu, A Oku, Y Sai, M Shimane, A Tsuji. Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance.
The Journal of pharmacology and experimental therapeutics.
1999 Nov; 291(2):778-84. doi:
. [PMID: 10525100] - T G Cooper, X S Wang, C H Yeung, L M Lewin. Successful lowering of epididymal carnitine by administration of pivalate to rats.
International journal of andrology.
1997 Jun; 20(3):180-8. doi:
10.1046/j.1365-2605.1997.00059.x. [PMID: 9354188] - K Abrahamsson, B O Eriksson, E Holme, U Jodal, A Jönsson, S Lindstedt. Pivalic acid-induced carnitine deficiency and physical exercise in humans.
Metabolism: clinical and experimental.
1996 Dec; 45(12):1501-7. doi:
10.1016/s0026-0495(96)90179-1. [PMID: 8969283] - P B Bianchi, A T Davis. beta-Hydroxybutyrate oxidation is reduced and hepatic balance of ketone bodies and free fatty acids is unaltered in carnitine-depleted, pivalate-treated rats.
The Journal of nutrition.
1996 Nov; 126(11):2867-72. doi:
10.1093/jn/126.11.2867. [PMID: 8914959] - P B Bianchi, D C Lehotay, A T Davis. Carnitine supplementation ameliorates the steatosis and ketosis induced by pivalate in rats.
The Journal of nutrition.
1996 Nov; 126(11):2873-9. doi:
10.1093/jn/126.11.2873. [PMID: 8914960] - H Nakajima, N Kodo, F Inoue, Z Kizaki, S Nukina, A Kinugasa, T Sawada. Pivalate affects carnitine status but causes no severe metabolic changes in rat liver.
The Journal of nutrition.
1996 Jun; 126(6):1683-7. doi:
10.1093/jn/126.6.1683. [PMID: 8648443] - C C Metges, K J Petzke, U Hennig. Gas chromatography/combustion/isotope ratio mass spectrometric comparison of N-acetyl- and N-pivaloyl amino acid esters to measure 15N isotopic abundances in physiological samples: a pilot study on amino acid synthesis in the upper gastro-intestinal tract of minipigs.
Journal of mass spectrometry : JMS.
1996 Apr; 31(4):367-76. doi:
10.1002/(sici)1096-9888(199604)31:4<367::aid-jms310>3.0.co;2-v. [PMID: 8799283] - U Zanelli, P Puccini, D Acerbi, P Ventura, P G Gervasi. Induction of peroxisomal beta-oxidation and P-450 4A-dependent activities by pivalic and trichloroacetic acid in rat liver and kidney.
Archives of toxicology.
1996; 70(3-4):145-9. doi:
10.1007/s002040050253. [PMID: 8825670] - K Abrahamsson, M Mellander, B O Eriksson, E Holme, U Jodal, A Jönsson, S Lindstedt. Transient reduction of human left ventricular mass in carnitine depletion induced by antibiotics containing pivalic acid.
British heart journal.
1995 Dec; 74(6):656-9. doi:
10.1136/hrt.74.6.656. [PMID: 8541173] - K Mizojiri, S Futaguchi, R Norikura, Y Katsuyama, T Nagasaki, T Yoshimori, M Nakanishi. Disposition of S-1108, a new oral cephem antibiotic, and metabolic fate of pivalic acid liberated from [pivaloyl-14C]S-1108 in rats and dogs.
Antimicrobial agents and chemotherapy.
1995 07; 39(7):1445-53. doi:
10.1128/aac.39.7.1445. [PMID: 7492083] - K Abrahamsson, E Holme, U Jodal, S Lindstedt, I Nordin. Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration--a risk irrespective of age.
Biochemical and molecular medicine.
1995 Jun; 55(1):77-9. doi:
10.1006/bmme.1995.1036. [PMID: 7551831] - T L Broderick, D DiDomenico, A L Shug, D J Paulson. L-propionylcarnitine effects on cardiac carnitine content and function in secondary carnitine deficiency.
Canadian journal of physiology and pharmacology.
1995 Apr; 73(4):509-14. doi:
10.1139/y95-064. [PMID: 7671193] - T L Broderick, S C Christos, B A Wolf, D DiDomenico, A L Shug, D J Paulson. Fatty acid oxidation and cardiac function in the sodium pivalate model of secondary carnitine deficiency.
Metabolism: clinical and experimental.
1995 Apr; 44(4):499-505. doi:
10.1016/0026-0495(95)90058-6. [PMID: 7723673] - Q N Diep, T Bøhmer, S Skrede. Formation of pivaloylcarnitine in heart and brown adipose tissue in the rat.
Biochimica et biophysica acta.
1995 Jan; 1243(1):65-70. doi:
10.1016/0304-4165(94)00129-l. [PMID: 7827109] - A T Davis. Carnitine depletion in rat pups of lactating mothers given sodium pivalate.
Biology of the neonate.
1995; 68(3):211-20. doi:
10.1159/000244239. [PMID: 8534786] - K Abrahamsson, B O Eriksson, E Holme, U Jodal, S Lindstedt, I Nordin. Impaired ketogenesis in carnitine depletion caused by short-term administration of pivalic acid prodrug.
Biochemical medicine and metabolic biology.
1994 Jun; 52(1):18-21. doi:
10.1006/bmmb.1994.1028. [PMID: 7917463] - B Melegh, B Sumegi, A D Sherry. Preferential elimination of pivalate with supplemental carnitine via formation of pivaloylcarnitine in man.
Xenobiotica; the fate of foreign compounds in biological systems.
1993 Nov; 23(11):1255-61. doi:
10.3109/00498259309059436. [PMID: 8310709] - R Fujii, S Chiba, K Numazaki, T Mori, I Terashima, H Meguro, A Mori, Y Toyonaga, K Sunakawa, Y Satoh. [Effect of cefditoren pivoxil on carnitine metabolism in pediatric patients].
The Japanese journal of antibiotics.
1993 Oct; 46(10):926-37. doi:
NULL. [PMID: 8254895] - K Shimizu, A Saito, J Shimada, M Ohmichi, Y Hiraga, T Inamatsu, K Shimada, M Tanimura, Y Fujita, T Nishikawa. Carnitine status and safety after administration of S-1108, a new oral cephem, to patients.
Antimicrobial agents and chemotherapy.
1993 May; 37(5):1043-9. doi:
10.1128/aac.37.5.1043. [PMID: 8517691] - M Konishi, H Hashimoto. Determination of pivaloylcarnitine in human plasma and urine by high-performance liquid chromatography with fluorescence detection.
Journal of pharmaceutical sciences.
1992 Oct; 81(10):1038-41. doi:
10.1002/jps.2600811017. [PMID: 1432617] - E Holme, U Jodal, S Linstedt, I Nordin. Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children.
Scandinavian journal of clinical and laboratory investigation.
1992 Sep; 52(5):361-72. doi:
10.3109/00365519209088371. [PMID: 1514015] - M Nakashima, T Uematsu, T Oguma, T Yoshida, K Mizojiri, S Matsuno, S Yamamoto. Phase I clinical studies of S-1108: safety and pharmacokinetics in a multiple-administration study with special emphasis on the influence on carnitine body stores.
Antimicrobial agents and chemotherapy.
1992 Apr; 36(4):762-8. doi:
10.1128/aac.36.4.762. [PMID: 1503438] - K Totsuka, K Shimizu, M Konishi, S Yamamoto. Metabolism of S-1108, a new oral cephem antibiotic, and metabolic profiles of its metabolites in humans.
Antimicrobial agents and chemotherapy.
1992 Apr; 36(4):757-61. doi:
10.1128/aac.36.4.757. [PMID: 1503437] - P B Bianchi, A T Davis. Sodium pivalate treatment reduces tissue carnitines and enhances ketosis in rats.
The Journal of nutrition.
1991 Dec; 121(12):2029-36. doi:
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Carbohydrate research.
1991 Mar; 210(?):191-8. doi:
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Lancet (London, England).
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The American journal of physiology.
1989 May; 256(5 Pt 2):F862-8. doi:
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Biochemical pharmacology.
1987 Oct; 36(20):3405-9. doi:
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Journal of pharmaceutical sciences.
1987 May; 76(5):356-8. doi:
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Xenobiotica; the fate of foreign compounds in biological systems.
1985 Jun; 15(6):453-8. doi:
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