Sebacic acid (BioDeep_00000002588)
Secondary id: BioDeep_00000229702, BioDeep_00000400416, BioDeep_00000415741, BioDeep_00000860441
natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
描述信息
Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD), also known as glutaric aciduria type II (GAII), a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials (PMID: 10556649, 1738216, 8442769, 12706375).
Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion.
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4109; ORIGINAL_PRECURSOR_SCAN_NO 4104
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4132; ORIGINAL_PRECURSOR_SCAN_NO 4130
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4118; ORIGINAL_PRECURSOR_SCAN_NO 4114
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4132; ORIGINAL_PRECURSOR_SCAN_NO 4129
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4099; ORIGINAL_PRECURSOR_SCAN_NO 4095
CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4127; ORIGINAL_PRECURSOR_SCAN_NO 4123
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID S017
Decanedioic acid, a normal urinary acid, is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency.
Decanedioic acid, a normal urinary acid, is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency.
同义名列表
29 个代谢物同义名
Sebacic acid, monocadmium salt; Sebacic acid, aluminum salt; 1,8-Octanedicarboxylic acid; Sebacic acid, sodium salt; 1,8-Octanedicarboxylate; Decanedicarboxylic acid; 4-Oxodecanedioic acid; 1,10-Decanedioic acid; Dicarboxylic acid C10; 4,7-Dioxosebacic acid; 1,8-Dicarboxyoctane; N-Decanedioic acid; 4-Oxodecanedioate; 1,10-Decanedioate; Decanedioic acid; Acide sebacique; N-Decanedioate; Sebacinsaeure; Sebacic acids; Sebacic acid; Decanedioate; Seracic acid; Sebacinsaure; Ipomic acid; Iponic acid; FA 10:1;O2; Sebacate; Sebacic acid; Sebacic acid
数据库引用编号
41 个数据库交叉引用编号
- ChEBI: CHEBI:41865
- KEGG: C08277
- PubChem: 5192
- HMDB: HMDB0000792
- Metlin: METLIN4240
- DrugBank: DB07645
- ChEMBL: CHEMBL1232164
- Wikipedia: Sebacic_acid
- LipidMAPS: LMFA01170006
- MetaCyc: CPD-3623
- KNApSAcK: C00001202
- foodb: FDB022247
- chemspider: 5004
- CAS: 26776-29-4
- CAS: 111-20-6
- MoNA: KO001811
- MoNA: KO001809
- MoNA: PS033902
- MoNA: LU067151
- MoNA: PS033901
- MoNA: KO001810
- MoNA: PS033907
- MoNA: LU067152
- MoNA: LU067156
- MoNA: KO001808
- MoNA: LU067153
- MoNA: LU067154
- MoNA: KO001807
- MoNA: PS033910
- MoNA: LU067155
- MoNA: PS033908
- MoNA: PR100605
- PMhub: MS000004042
- PubChem: 10475
- PDB-CCD: DEC
- 3DMET: B02155
- NIKKAJI: J10.109E
- RefMet: Sebacic acid
- medchemexpress: HY-W014787
- KNApSAcK: 41865
- LOTUS: LTS0251393
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)
38 个相关的物种来源信息
- 165353 - Angelica sinensis (Oliv.)Diels: -
- 7458 - Apidae: LTS0251393
- 7459 - Apis: LTS0251393
- 7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
- 7461 - Apis cerana: LTS0251393
- 6656 - Arthropoda: LTS0251393
- 3700 - Brassicaceae: LTS0251393
- 53845 - Caesalpinia: LTS0251393
- 53846 - Caesalpinia pulcherrima: 10.1021/NP0201523
- 53846 - Caesalpinia pulcherrima: LTS0251393
- 66169 - Cephalotaxus fortunei: -
- 7227 - Drosophila melanogaster: 10.1038/S41467-019-11933-Z
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 33682 - Euglenozoa: LTS0251393
- 2759 - Eukaryota: LTS0251393
- 3803 - Fabaceae: LTS0251393
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 50557 - Insecta: LTS0251393
- 161755 - Isatis: LTS0251393
- 161756 - Isatis tinctoria: 10.1055/S-2006-958019
- 161756 - Isatis tinctoria: LTS0251393
- 5653 - Kinetoplastea: LTS0251393
- 3398 - Magnoliopsida: LTS0251393
- 33208 - Metazoa: LTS0251393
- 3883 - Phaseolus: LTS0251393
- 3885 - Phaseolus vulgaris: 10.1246/BCSJ.60.981
- 3885 - Phaseolus vulgaris: LTS0251393
- 3988 - Ricinus communis L.: -
- 35493 - Streptophyta: LTS0251393
- 58023 - Tracheophyta: LTS0251393
- 5690 - Trypanosoma: LTS0251393
- 5691 - Trypanosoma brucei:
- 5691 - Trypanosoma brucei: 10.1128/AAC.00044-13
- 5691 - Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
- 5691 - Trypanosoma brucei: LTS0251393
- 5654 - Trypanosomatidae: LTS0251393
- 33090 - Viridiplantae: LTS0251393
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
- Zhipeng Dai, Minyan Dang, Wenzhi Zhang, Sumathra Murugan, Seoh Wei Teh, Haiyan Pan. Biomimetic hydroxyapatite/poly xylitol sebacic adibate/vitamin K nanocomposite for enhancing bone regeneration.
Artificial cells, nanomedicine, and biotechnology.
2019 Dec; 47(1):1898-1907. doi:
10.1080/21691401.2019.1573183
. [PMID: 31066314] - Qi-Rui Bi, Jin-Jun Hou, Min Yang, Yao Shen, Peng Qi, Rui-Hong Feng, Zhuo Dai, Bing-Peng Yan, Jian-Wei Wang, Xiao-Jian Shi, Wan-Ying Wu, De-An Guo. A Strategy Combining Higher Energy C-Trap Dissociation with Neutral Loss- and Product Ion-Based MSn Acquisition for Global Profiling and Structure Annotation of Fatty Acids Conjugates.
Journal of the American Society for Mass Spectrometry.
2017 03; 28(3):443-451. doi:
10.1007/s13361-016-1558-y
. [PMID: 27924497] - N A Ushakova, E S Brodskii, A A Kovalenko, A I Bastrakov, A A Kozlova, D S Pavlov. Characteristics of lipid fractions of larvae of the black soldier fly Hermetia illucens.
Doklady. Biochemistry and biophysics.
2016 May; 468(1):209-12. doi:
10.1134/s1607672916030145
. [PMID: 27417723] - M Gołębiowski, M Cerkowniak, A Urbanek, M Dawgul, W Kamysz, M I Boguś, D Sosnowska, P Stepnowski. Antimicrobial activity of untypical lipid compounds in the cuticular and internal lipids of four fly species.
Journal of applied microbiology.
2014 Feb; 116(2):269-87. doi:
10.1111/jam.12370
. [PMID: 24238211] - Brenda R Carrillo-Conde, Amanda E Ramer-Tait, Michael J Wannemuehler, Balaji Narasimhan. Chemistry-dependent adsorption of serum proteins onto polyanhydride microparticles differentially influences dendritic cell uptake and activation.
Acta biomaterialia.
2012 Oct; 8(10):3618-28. doi:
10.1016/j.actbio.2012.06.001
. [PMID: 22684115] - A Nakai. [Floppy female infant with congenital hydrocephalus, hepatic dysfunction and refractory convulsions].
No to hattatsu = Brain and development.
2011 Nov; 43(6):433-4. doi:
NULL
. [PMID: 22180956] - Michael H Chiu, Elmar J Prenner. Differential scanning calorimetry: An invaluable tool for a detailed thermodynamic characterization of macromolecules and their interactions.
Journal of pharmacy & bioallied sciences.
2011 Jan; 3(1):39-59. doi:
10.4103/0975-7406.76463
. [PMID: 21430954] - M Membrez, C J Chou, F Raymond, R Mansourian, M Moser, I Monnard, C Ammon-Zufferey, K Mace, G Mingrone, C Binnert. Six weeks' sebacic acid supplementation improves fasting plasma glucose, HbA1c and glucose tolerance in db/db mice.
Diabetes, obesity & metabolism.
2010 Dec; 12(12):1120-6. doi:
10.1111/j.1463-1326.2010.01308.x
. [PMID: 20977585] - Swati A Guhagarkar, Rajiv V Gaikwad, Abdul Samad, Vinod C Malshe, Padma V Devarajan. Polyethylene sebacate-doxorubicin nanoparticles for hepatic targeting.
International journal of pharmaceutics.
2010 Nov; 401(1-2):113-22. doi:
10.1016/j.ijpharm.2010.09.012
. [PMID: 20854883] - Udayanath Aich, M Adam Meledeo, Srinivasa-Gopalan Sampathkumar, Jie Fu, Mark B Jones, Christopher A Weier, Sung Yun Chung, Benjamin C Tang, Ming Yang, Justin Hanes, Kevin J Yarema. Development of delivery methods for carbohydrate-based drugs: controlled release of biologically-active short chain fatty acid-hexosamine analogs.
Glycoconjugate journal.
2010 May; 27(4):445-59. doi:
10.1007/s10719-010-9292-3
. [PMID: 20458533] - Xiaohua Liu, Glenda J Pettway, Laurie K McCauley, Peter X Ma. Pulsatile release of parathyroid hormone from an implantable delivery system.
Biomaterials.
2007 Oct; 28(28):4124-31. doi:
10.1016/j.biomaterials.2007.05.034
. [PMID: 17576005] - Guilherme L Sassaki, Philip A J Gorin, Rodrigo A Reis, Rodrigo V Serrato, Selene L Elífio, Marcello Iacomini. Carbohydrate, glycolipid, and lipid components from the photobiont (Scytonema sp.) of the lichen, Dictyomema glabratum.
Carbohydrate research.
2005 Aug; 340(11):1808-17. doi:
10.1016/j.carres.2005.05.004
. [PMID: 15963960] - Alexandra Muth, Jochen Jung, Steffi Bilke, Annette Scharrer, Armin Mosandl, Adrian C Sewell, Hans Böhles. Simultaneous enantioselective analysis of chiral urinary metabolites in patients with Zellweger syndrome.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 Jul; 792(2):269-77. doi:
10.1016/s1570-0232(03)00285-x
. [PMID: 12860034] - J R Harris. In vitro fibrillogenesis of the amyloid beta 1-42 peptide: cholesterol potentiation and aspirin inhibition.
Micron (Oxford, England : 1993).
2002; 33(7-8):609-26. doi:
10.1016/s0968-4328(02)00029-x
. [PMID: 12475558] - S Yamaguchi, M Iga, M Kimura, Y Suzuki, N Shimozawa, T Fukao, N Kondo, Y Tazawa, T Orii. Urinary organic acids in peroxisomal disorders: a simple screening method.
Journal of chromatography. B, Biomedical sciences and applications.
2001 Jul; 758(1):81-6. doi:
10.1016/s0378-4347(01)00102-5
. [PMID: 11482738] - E Capristo, G Mingrone, A De Gaetano, G Addolorato, A V Greco, G Gasbarrini. A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples.
Clinica chimica acta; international journal of clinical chemistry.
1999 Nov; 289(1-2):11-21. doi:
10.1016/s0009-8981(99)00145-x
. [PMID: 10556649] - A M Favuzzi, G Mingrone, A Bertuzzi, S Salinari, A Gandolfi, A V Greco. Pharmacokinetics of sebacic acid in rats.
European review for medical and pharmacological sciences.
1999 May; 3(3):119-25. doi:
. [PMID: 10827815]
- T Hagen, M S Korson, M Sakamoto, J E Evans. A GC/MS/MS screening method for multiple organic acidemias from urine specimens.
Clinica chimica acta; international journal of clinical chemistry.
1999 May; 283(1-2):77-88. doi:
10.1016/s0009-8981(99)00037-6
. [PMID: 10404733] - G Liu, B Hinch, A D Beavis. Mechanisms for the transport of alpha,omega-dicarboxylates through the mitochondrial inner membrane.
The Journal of biological chemistry.
1996 Oct; 271(41):25338-44. doi:
10.1074/jbc.271.41.25338
. [PMID: 8810298] - A J Domb, M Rock, C Perkin, G Yipchuck, B Broxup, J G Villemure. Excretion of a radiolabelled anticancer biodegradable polymeric implant from the rabbit brain.
Biomaterials.
1995 Sep; 16(14):1069-72. doi:
10.1016/0142-9612(95)98902-q
. [PMID: 8519927] - A J Domb, M Rock, J Schwartz, C Perkin, G Yipchuk, B Broxup, J G Villemure. Metabolic disposition and elimination studies of a radiolabelled biodegradable polymeric implant in the rat brain.
Biomaterials.
1994 Jul; 15(9):681-8. doi:
10.1016/0142-9612(94)90166-x
. [PMID: 7948590] - C A Raguso, G Mingrone, A V Greco, P A Tataranni, A De Gaetano, M Castagneto. Dicarboxylic acids and glucose utilization in humans: effect of sebacate.
JPEN. Journal of parenteral and enteral nutrition.
1994 Jan; 18(1):9-13. doi:
10.1177/014860719401800109
. [PMID: 8164314] - J J Pitt, A Poulos. Excretion of 3,6-epoxydicarboxylic acids in peroxisomal disorders.
Clinica chimica acta; international journal of clinical chemistry.
1993 Dec; 223(1-2):23-9. doi:
10.1016/0009-8981(93)90059-d
. [PMID: 7511488] - G Mingrone, A V Greco, M Castagneto, A De Gaetano, P A Tataranni, C Raguso. Kinetics and thermogenesis of medium-chain monocarboxylic and dicarboxylic acids in man: sebacate and medium-chain triglycerides.
JPEN. Journal of parenteral and enteral nutrition.
1993 May; 17(3):257-64. doi:
10.1177/0148607193017003257
. [PMID: 8505832] - A Bertuzzi, E Finotti, G Mingrone, A V Greco. Sebacic acid binding to human plasma albumin.
Biochemical pharmacology.
1993 Feb; 45(3):697-702. doi:
10.1016/0006-2952(93)90145-m
. [PMID: 8442769] - A V Greco, G Mingrone, C Raguso, A Tataranni, E Finotti, R M Tacchino, E Capristo, A De Gaetano, M Castagneto. Metabolic effects and disposition of sebacate, an alternate dicarboxylic fuel substrate.
Annals of nutrition & metabolism.
1992; 36(1):1-11. doi:
10.1159/000177693
. [PMID: 1590667] - G Mingrone, R M Tacchino, M Castagneto, E Finotti, A V Greco. Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate.
JPEN. Journal of parenteral and enteral nutrition.
1992 Jan; 16(1):32-8. doi:
10.1177/014860719201600132
. [PMID: 1738216] - M J Bennett, M C Ragni, I Hood, D E Hale. Azelaic and pimelic acids: metabolic intermediates or artefacts?.
Journal of inherited metabolic disease.
1992; 15(2):220-3. doi:
10.1007/bf01799635
. [PMID: 1527989] - P A Tataranni, G Mingrone, A De Gaetano, C Raguso, A V Greco. Tracer study of metabolism and tissue distribution of sebacic acid in rats.
Annals of nutrition & metabolism.
1992; 36(5-6):296-303. doi:
10.1159/000177733
. [PMID: 1492757] - G Mingrone, A V Greco, A Bertuzzi, E Arcieri-Mastromattei, R M Tacchino, F Marino, E Finotti, M Castagneto. Tissue uptake and oxidation of disodium sebacate in man.
JPEN. Journal of parenteral and enteral nutrition.
1991 Jul; 15(4):454-9. doi:
10.1177/0148607191015004454
. [PMID: 1910110] - H Brem, M S Mahaley, N A Vick, K L Black, S C Schold, P C Burger, A H Friedman, I S Ciric, T W Eller, J W Cozzens. Interstitial chemotherapy with drug polymer implants for the treatment of recurrent gliomas.
Journal of neurosurgery.
1991 Mar; 74(3):441-6. doi:
10.3171/jns.1991.74.3.0441
. [PMID: 1993909] - H Böhles, Z Akcetin, W Lehnert. The influence of i.v. MCT and carnitine on the excretion of dicarboxylic acids.
Beitrage zu Infusionstherapie und klinische Ernahrung.
1988; 20(?):69-74. doi:
NULL
. [PMID: 3132147] - N Gregersen, P B Mortensen, S Kølvraa. On the biologic origin of C6-C10-dicarboxylic and C6-C10-omega-1-hydroxy monocarboxylic acids in human and rat with acyl-CoA dehydrogenation deficiencies: in vitro studies on the omega- and omega-1-oxidation of medium-chain (C6-C12) fatty acids in human and rat liver.
Pediatric research.
1983 Oct; 17(10):828-34. doi:
10.1203/00006450-198310000-00013
. [PMID: 6634246] - N Gregersen, S Kølvraa, K Rasmussen, P B Mortensen, P Divry, M David, N Hobolth. General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases.
Clinica chimica acta; international journal of clinical chemistry.
1983 Aug; 132(2):181-91. doi:
10.1016/0009-8981(83)90246-2
. [PMID: 6616873] - N Gregersen, S Kølvraa, P B Mortensen, K Rasmussen. C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects.
Scandinavian journal of clinical and laboratory investigation. Supplementum.
1982; 161(?):15-27. doi:
10.3109/00365518209168396
. [PMID: 6959231] - P B Mortensen. Urinary excretion of C4--C10-dicarboxylic acids and antiketogenic properties of adipic acid in ketogenic-stimulated rats due to diabetes, long-chain and short-chain monocarboxylic acids.
Biochimica et biophysica acta.
1981 May; 664(2):335-48. doi:
10.1016/0005-2760(81)90056-4
. [PMID: 7248329] - P B Mortensen. C6--C10-dicarboxylic aciduria in starved, fat-fed and diabetic rats receiving decanoic acid or medium-chain triacylglycerol. An in vivo measure of the rate of beta-oxidation of fatty acids.
Biochimica et biophysica acta.
1981 May; 664(2):349-55. doi:
10.1016/0005-2760(81)90057-6
. [PMID: 7248330] - P B Mortensen, N Gregersen, S Kølvraa, E Christensen. The occurrence of C6--C10-dicarboxylic acids in urine from patients and rats treated with dipropylacetate.
Biochemical medicine.
1980 Oct; 24(2):153-61. doi:
10.1016/0006-2944(80)90006-x
. [PMID: 6779814] - N Gregersen, F Rosleff, S Kølvraa, N Hobolth, K Rasmussen, R Lauritzen. Non-ketotic C6-C10-dicarboxylic aciduria: biochemical investigations of two cases.
Clinica chimica acta; international journal of clinical chemistry.
1980 Mar; 102(2-3):179-89. doi:
10.1016/0009-8981(80)90031-5
. [PMID: 6892795]