Dodecanedioic acid (BioDeep_00000001597)

 

Secondary id: BioDeep_00000405314

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


Dodecanedioic acid, sodium salt

化学式: C12H22O4 (230.1518)
中文名称: 十二烷二酸
谱图信息: 最多检出来源 Homo sapiens(feces) 16.39%

Reviewed

Last reviewed on 2024-07-17.

Cite this Page

Dodecanedioic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dodecanedioic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001597). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CCCCCC(=O)O)CCCCC(=O)O
InChI: InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)

描述信息

Dodecanedioic acid is an aliphatic dicarboxylic acid containing 12 carbon atoms. More formally it is an alpha,omega-dicarboxylic acid with both the first and last carbons of the aliphatic chain having carboxylic acids. Dodecanedioic acid is water soluble. It can be produced in yeast and fungi through the oxidation of dodecane via fungal peroxygenases (PMID: 27573441). High levels of dodecanedioic acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency (PMID: 16146704). CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. It is thought that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes (PMID: 16146704). CPT IA deficiency is characterized by acute encephalopathy with hypoglycemia and hepatomegaly.
Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates. (PMID 9591306). Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency. CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes. (PMID: 16146704) [HMDB]
Dodecanedioic acid (C12) is a dicarboxylic acid with a metabolic pathway intermediate to those of lipids and carbohydrates.

同义名列表

19 个代谢物同义名

Dodecanedioic acid, sodium salt; Decamethylenedicarboxylic acid; 1,10-Decanedicarboxylic acid; Decamethylenedicarboxylate; N-Dodecane-a,W-dioic acid; 1,10-Decanedicarboxylate; 1,12-Dodecanedioic acid; N-Dodecane-a,W-dioate; N-Dodecanedioic acid; 1,10-Dicarboxydecane; 1,12-Dodecanedioate; DODECANEDIOIC ACID; Dodecandioic acid; N-Dodecanedioate; Dodecanedioate; Corfree m 2; FA 12:1;O2; SL-AH; Dodecanedioic acid



数据库引用编号

31 个数据库交叉引用编号

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)

30 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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ALB, CASP9, OPA1, PFDN5
Peripheral membrane protein 2 CYP1B1, HSD17B6
Endoplasmic reticulum membrane 2 CYP1B1, HSP90B1
Nucleus 5 ALB, CASP9, HSP90B1, NSL1, PFDN5
cytosol 10 ACOX1, ALB, CASP9, EHHADH, GSR, HSP90B1, LIPE, NSL1, OPA1, PFDN5
dendrite 1 OPA1
mitochondrial membrane 1 OPA1
centrosome 1 ALB
nucleoplasm 3 ENY2, NSL1, OPA1
Cell membrane 2 CX3CR1, LIPE
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 CX3CR1
cell surface 2 CX3CR1, TNR
glutamatergic synapse 1 TNR
Golgi apparatus 1 ALB
Golgi membrane 1 INS
mitochondrial inner membrane 1 OPA1
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 LIPE
plasma membrane 1 CX3CR1
Membrane 5 ACOX1, CYP1B1, HSP90B1, LIPE, OPA1
caveola 1 LIPE
extracellular exosome 4 ALB, BMP3, GSR, HSP90B1
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 ALB, HSD17B6, HSP90B1
extracellular space 5 ALB, BMP3, IL10, INS, TNR
perinuclear region of cytoplasm 2 CX3CR1, HSP90B1
Schaffer collateral - CA1 synapse 1 TNR
mitochondrion 6 CASP9, CYP1B1, ENY2, GSR, NSL1, OPA1
protein-containing complex 3 ALB, CASP9, HSP90B1
intracellular membrane-bounded organelle 2 CYP1B1, HSD17B6
Microsome membrane 2 CYP1B1, HSD17B6
Secreted 5 ALB, BMP3, IL10, INS, SMR3A
extracellular region 7 ALB, BMP3, HSP90B1, IL10, INS, SMR3A, TNR
Single-pass membrane protein 1 OPA1
mitochondrial outer membrane 1 OPA1
neuronal cell body membrane 1 CX3CR1
mitochondrial matrix 1 GSR
anchoring junction 1 ALB
external side of plasma membrane 2 CX3CR1, GSR
Secreted, extracellular space, extracellular matrix 1 TNR
axon cytoplasm 1 OPA1
midbody 1 HSP90B1
Mitochondrion inner membrane 1 OPA1
Membrane raft 1 TNR
focal adhesion 1 HSP90B1
microtubule 1 OPA1
Peroxisome 2 ACOX1, EHHADH
peroxisomal matrix 2 ACOX1, EHHADH
peroxisomal membrane 1 ACOX1
Mitochondrion intermembrane space 1 OPA1
mitochondrial intermembrane space 1 OPA1
collagen-containing extracellular matrix 2 HSP90B1, TNR
nuclear speck 1 NSL1
neuron projection 1 CX3CR1
ciliary basal body 1 ALB
Chromosome 1 HMCES
centriole 1 ALB
mitochondrial crista 1 OPA1
spindle pole 2 ALB, NSL1
blood microparticle 1 ALB
nuclear pore 1 ENY2
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Chromosome, centromere, kinetochore 1 NSL1
NSL complex 1 NSL1
Nucleus, nucleoplasm 1 ENY2
Melanosome 1 HSP90B1
replication fork 1 HMCES
sperm plasma membrane 1 HSP90B1
intermediate filament cytoskeleton 1 PFDN5
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, HSP90B1, INS
MLL1 complex 1 NSL1
transcription factor TFTC complex 1 ENY2
platelet alpha granule lumen 1 ALB
kinetochore 1 NSL1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
perineuronal net 1 TNR
apoptosome 1 CASP9
outer kinetochore 1 NSL1
Sarcoplasmic reticulum lumen 1 HSP90B1
nuclear pore nuclear basket 1 ENY2
transcription export complex 2 1 ENY2
prefoldin complex 1 PFDN5
SAGA complex 1 ENY2
histone acetyltransferase complex 1 NSL1
[Dynamin-like GTPase OPA1, long form]: Mitochondrion inner membrane 1 OPA1
[Dynamin-like GTPase OPA1, short form]: Mitochondrion intermembrane space 1 OPA1
endocytic vesicle lumen 1 HSP90B1
endoplasmic reticulum chaperone complex 1 HSP90B1
macropinosome membrane 1 CX3CR1
tenascin complex 1 TNR
dendritic tree 1 CX3CR1
ciliary transition fiber 1 ALB
caspase complex 1 CASP9
DUBm complex 1 ENY2
MIS12/MIND type complex 1 NSL1


文献列表

  • Juan Cruz Carrizo, Sung Vo Duy, Gabriel Munoz, Guido Marconi, María Valeria Amé, Sébastien Sauvé. Suspect screening of pharmaceuticals, illicit drugs, pesticides, and other emerging contaminants in Argentinean Piaractus mesopotamicus, a fish species used for local consumption and export. Chemosphere. 2022 Dec; 309(Pt 1):136769. doi: 10.1016/j.chemosphere.2022.136769. [PMID: 36209849]
  • Irina Funk, Nina Rimmel, Christoph Schorsch, Volker Sieber, Jochen Schmid. Production of dodecanedioic acid via biotransformation of low cost plant-oil derivatives using Candida tropicalis. Journal of industrial microbiology & biotechnology. 2017 Oct; 44(10):1491-1502. doi: 10.1007/s10295-017-1972-6. [PMID: 28756564]
  • Jun Niu, Zifeng Pi, Hao Yue, Yang Wang, Qing Yu, Shuying Liu. Effect of ginseng polysaccharide on the urinary excretion of type 2 diabetic rats studied by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Oct; 907(?):7-12. doi: 10.1016/j.jchromb.2012.08.012. [PMID: 22998979]
  • 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]
  • Francesco M Megli, Luciana Russo. Different oxidized phospholipid molecules unequally affect bilayer packing. Biochimica et biophysica acta. 2008 Jan; 1778(1):143-52. doi: 10.1016/j.bbamem.2007.09.014. [PMID: 18054893]
  • N Weber, K Bergander, E Fehling, E Klein, K Vosmann, K D Mukherjee. Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols. Applied microbiology and biotechnology. 2006 Apr; 70(3):290-7. doi: 10.1007/s00253-005-027-5. [PMID: 16007456]
  • Simona Panunzi, Andrea De Gaetano, Geltrude Mingrone. Approximate linear confidence and curvature of a kinetic model of dodecanedioic acid in humans. American journal of physiology. Endocrinology and metabolism. 2005 Nov; 289(5):E915-22. doi: 10.1152/ajpendo.00503.2003. [PMID: 15972268]
  • Stanley H Korman, Hans R Waterham, Alisa Gutman, Cornelis Jakobs, Ronald J A Wanders. Novel metabolic and molecular findings in hepatic carnitine palmitoyltransferase I deficiency. Molecular genetics and metabolism. 2005 Nov; 86(3):337-43. doi: 10.1016/j.ymgme.2005.07.022. [PMID: 16146704]
  • A Bertuzzi, G Mingrone, A Gandolfi, A V Greco, S Salinari. Disposition of dodecanedioic acid in humans. The Journal of pharmacology and experimental therapeutics. 2000 Mar; 292(3):846-52. doi: NULL. [PMID: 10688596]
  • 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]
  • G Mingrone, A De Gaetano, A V Greco, E Capristo, G Benedetti, M Castagneto, G Gasbarrini. Comparison between dodecanedioic acid and long-chain triglycerides as an energy source in liquid formula diets. JPEN. Journal of parenteral and enteral nutrition. 1999 Mar; 23(2):80-4. doi: 10.1177/014860719902300280. [PMID: 10081997]
  • A de Gaetano, G Mingrone, M Castagneto, G Benedetti, A V Greco, G Gasbarrini. Kinetics of dodecanedioic acid triglyceride in rats. The American journal of physiology. 1999 03; 276(3):E497-502. doi: 10.1152/ajpendo.1999.276.3.e497. [PMID: 10070016]
  • A V Greco, G Mingrone, E Capristo, G Benedetti, A De Gaetano, G Gasbarrini. The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients. Nutrition (Burbank, Los Angeles County, Calif.). 1998 Apr; 14(4):351-7. doi: 10.1016/s0899-9007(97)00502-9. [PMID: 9591306]
  • G Mingrone, A De Gaetano, A V Greco, E Capristo, G Benedetti, M Castagneto, G Gasbarrini. Dodecanedioic acid infusion induces a sparing effect on whole-body glucose uptake, mainly in non-insulin-dependent diabetes mellitus. The British journal of nutrition. 1997 Nov; 78(5):723-35. doi: 10.1079/bjn19970190. [PMID: 9389896]
  • A Bertuzzi, G Mingrone, A De Gaetano, A Gandolfi, A V Greco, S Salinari. Kinetics of dodecanedioic acid and effect of its administration on glucose kinetics in rats. The British journal of nutrition. 1997 Jul; 78(1):143-53. doi: 10.1079/bjn19970126. [PMID: 9292767]
  • A V Greco, G Mingrone, A De Gaetano, L Amigo, L Puglielli, M Castagneto, F Nervi. Uptake of dodecanedioic acid by isolated rat liver. Clinica chimica acta; international journal of clinical chemistry. 1997 Feb; 258(2):209-18. doi: 10.1016/s0009-8981(96)06457-1. [PMID: 9074817]
  • G Mingrone, A De Gaetano, A V Greco, G Benedetti, E Capristo, M Castagneto, G Gasbarrini. Plasma clearance and oxidation of dodecanedioic acid in humans. JPEN. Journal of parenteral and enteral nutrition. 1996 Jan; 20(1):38-42. doi: 10.1177/014860719602000138. [PMID: 8788261]
  • A Bertuzzi, G Mingrone, A Gandolfi, A V Greco, S Salinari. Pharmacokinetic analysis of dodecanedioic acid in humans from bolus data. JPEN. Journal of parenteral and enteral nutrition. 1995 Nov; 19(6):498-501. doi: 10.1177/0148607195019006498. [PMID: 8748365]
  • G Mingrone, A V Greco, A De Gaetano, A Tataranni, C Raguso, M Castagneto. Pharmacokinetic profile of dodecanedioic acid, a proposed alternative fuel substrate. JPEN. Journal of parenteral and enteral nutrition. 1994 May; 18(3):225-30. doi: 10.1177/0148607194018003225. [PMID: 8064997]
  • J Vamecq, J P Draye. Comparison between the formation and the oxidation of dicarboxylylcarnitine esters in rat liver and skeletal muscle: possible implications for human inborn disorders of mitochondrial beta-oxidation. Journal of inherited metabolic disease. 1989; 12(1):58-63. doi: 10.1007/bf01805531. [PMID: 2501584]
  • J P Draye, K Veitch, J Vamecq, F Van Hoof. Comparison of the metabolism of dodecanedioic acid in vivo in control, riboflavin-deficient and clofibrate-treated rats. European journal of biochemistry. 1988 Dec; 178(1):183-9. doi: 10.1111/j.1432-1033.1988.tb14442.x. [PMID: 3203687]
  • S Bergseth, B M Hokland, J Bremer. Metabolism of dicarboxylic acids in vivo and in the perfused kidney of the rat. Biochimica et biophysica acta. 1988 Jul; 961(1):103-9. doi: 10.1016/0005-2760(88)90135-x. [PMID: 3132982]
  • A S Breathnach, E J Robins, Y Bhasin, L Ethridge, M Nazzaro-Porro, S Passi, M Picardo. Observations on cell kinetics and viability of a human melanoma cell line exposed to dicarboxylic acids in tissue culture. Histology and histopathology. 1986 Jul; 1(3):235-9. doi: ". [PMID: 2980117]
  • E J Robins, A S Breathnach, B J Ward, Y P Bhasin, L Ethridge, M Nazzaro-Porro, S Passi, M Picardo. Effect of dicarboxylic acids on Harding-Passey and Cloudman S91 melanoma cells in tissue culture. The Journal of investigative dermatology. 1985 Sep; 85(3):216-21. doi: 10.1111/1523-1747.ep12276681. [PMID: 4031537]
  • B J Ward, A S Breathnach, E J Robins, Y Bhasin, L Ethridge, S Passi, M Nazzaro-Porro. Analytical, ultrastructural, autoradiographic and biochemical studies on [3H]dicarboxylic acid added to cultures of melanoma cells. The British journal of dermatology. 1984 Jul; 111(1):29-36. doi: 10.1111/j.1365-2133.1984.tb04013.x. [PMID: 6743538]
  • P Lalezari, M Kumar, K M Kumar, C Lawrence. Inhibition of cold insolubility of an IgA cryoglobulin by decanedicarboxylic acid and related compounds. American journal of hematology. 1983 Nov; 15(3):279-88. doi: 10.1002/ajh.2830150309. [PMID: 6638013]
  • S Passi, M Nazzaro-Porro, M Picardo, G Mingrone, P Fasella. Metabolism of straight saturated medium chain length (C9 to C12) dicarboxylic acids. Journal of lipid research. 1983 Sep; 24(9):1140-7. doi: 10.1016/s0022-2275(20)37897-4. [PMID: 6631243]