Hexadecanedioic acid (BioDeep_00000002192)

 

Secondary id: BioDeep_00000405329, BioDeep_00000629369, BioDeep_00000864762

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


N-Tetradecane-omega,omega-dicarboxylic acid

化学式: C16H30O4 (286.2144)
中文名称: 十六烷二酸, 十六碳二酸
谱图信息: 最多检出来源 Homo sapiens(feces) 14.33%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Hexadecanedioic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/hexadecanedioic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002192). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CCCCCCCC(=O)O)CCCCCCC(=O)O
InChI: InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)

描述信息

Hexadecanedioic acid, also known as thapsic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Hexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in the liver (PMID: 4372285). It has antitumor activity (PMID: 14987827).
Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in liver (PMID 4372285). It has an antitumor activity (PMID 14987827). Hexadecanedioic acid is found in sweet cherry and potato.
Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples.
Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples.

同义名列表

18 个代谢物同义名

N-Tetradecane-omega,omega-dicarboxylic acid; alpha,Omega-tetradecanedicarboxylic acid; N-Tetradecane-ω,ω’-dicarboxylic acid; N-Tetradecane-ω,ω-dicarboxylic acid; 1,14-Tetradecanedicarboxylic acid; Α,ω-tetradecanedicarboxylic acid; N-Tetradecane-ω,ω-dicarboxylate; 1,14-Tetradecanedicarboxylate; Α,ω-tetrαdecαnedicαrboxylαte; Hexadecane-1,16-dioic acid; 1,16-Hexadecanedioic acid; Hexadecane-1,16-dioate; 1,16-Hexadecanedioate; HEXADECANEDIOIC ACID; Hexadecanedioate; Thapsic acid; Thapsate; Hexadecanedioic acid



数据库引用编号

18 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)

32 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 8 APOB, CAT, CYP26B1, GDAP1, HPGDS, IRF6, MYH9, S100A12
Peripheral membrane protein 3 CYP26B1, HSD17B6, S100A12
Endosome membrane 1 APOB
Endoplasmic reticulum membrane 2 APOB, CYP26B1
Nucleus 4 GDAP1, IRF6, MYH9, S100A12
cytosol 10 APOB, CAT, CMBL, FBXL4, GDAP1, GDAP1L1, HPGDS, IRF6, MYH9, S100A12
nuclear body 1 MYH9
nucleoplasm 2 HPGDS, RBBP9
Cell membrane 3 CALCR, MYH9, S100A12
Cleavage furrow 1 MYH9
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 4 ABCC3, CALCR, GDAP1, UCP3
Golgi membrane 1 INS
mitochondrial inner membrane 1 UCP3
neuromuscular junction 1 MYH9
neuronal cell body 1 APOB
smooth endoplasmic reticulum 1 APOB
Cytoplasm, cytosol 1 CMBL
Lysosome 1 TMEM25
acrosomal vesicle 1 CALCR
plasma membrane 6 ABCC3, APOB, CALCR, MYH9, S100A12, TMEM25
Membrane 7 ABCC3, CALCR, CAT, GDAP1, GDAP1L1, MYH9, TMEM25
axon 1 CALCR
basolateral plasma membrane 1 ABCC3
brush border 1 MYH9
extracellular exosome 5 APOB, CAT, CMBL, IRF6, MYH9
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 2 APOB, INS
lysosomal lumen 1 APOB
adherens junction 1 MYH9
mitochondrion 6 CAT, FBXL4, GDAP1, GDAP1L1, MTFR2, UCP3
protein-containing complex 2 CAT, MYH9
intracellular membrane-bounded organelle 4 APOB, CAT, HPGDS, HSD17B6
Microsome membrane 2 CYP26B1, HSD17B6
Single-pass type I membrane protein 1 TMEM25
Secreted 3 APOB, INS, S100A12
extracellular region 5 APOB, CAT, INS, S100A12, TMEM25
cytoplasmic side of plasma membrane 1 MYH9
Mitochondrion outer membrane 1 GDAP1
mitochondrial outer membrane 1 GDAP1
[Isoform 2]: Secreted 1 TMEM25
mitochondrial matrix 1 CAT
chylomicron 1 APOB
low-density lipoprotein particle 1 APOB
very-low-density lipoprotein particle 1 APOB
actin cytoskeleton 1 MYH9
Early endosome 1 APOB
Mitochondrion inner membrane 1 UCP3
Cytoplasm, cytoskeleton 2 MYH9, S100A12
focal adhesion 2 CAT, MYH9
spindle 1 MYH9
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 2 CAT, GDAP1
mitochondrial intermembrane space 1 FBXL4
nuclear speck 1 FBXL4
actomyosin 1 MYH9
Late endosome 1 TMEM25
ruffle 1 MYH9
cilium 1 CALCR
chromatin 1 IRF6
cell leading edge 1 MYH9
supramolecular fiber 1 MYH9
cytoskeleton 1 S100A12
Cytoplasm, cell cortex 1 MYH9
Basolateral cell membrane 1 ABCC3
[Isoform 3]: Secreted 1 TMEM25
myosin filament 1 MYH9
myosin II complex 1 MYH9
endosome lumen 2 APOB, INS
Lipid droplet 1 APOB
myosin complex 1 MYH9
ubiquitin ligase complex 1 FBXL4
stress fiber 1 MYH9
basal plasma membrane 1 ABCC3
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 3 CAT, INS, S100A12
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 APOB, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
endoplasmic reticulum exit site 1 APOB
immunological synapse 1 MYH9
clathrin-coated endocytic vesicle membrane 1 APOB
uropod 1 MYH9
Basal cell membrane 1 ABCC3
[Isoform 1]: Cell membrane 1 TMEM25
amylin receptor complex 3 1 CALCR
protein phosphatase type 1 complex 1 PPP1R3D
endocytic vesicle lumen 1 APOB
chylomicron remnant 1 APOB
intermediate-density lipoprotein particle 1 APOB
catalase complex 1 CAT
mature chylomicron 1 APOB
Cytoplasmic vesicle, secretory vesicle, Cortical granule 1 MYH9
cortical granule 1 MYH9
SCF ubiquitin ligase complex 1 FBXL4
[Isoform 4]: Cell membrane 1 TMEM25
amylin receptor complex 1 1 CALCR
amylin receptor complex 2 1 CALCR
actomyosin contractile ring 1 MYH9
myosin II filament 1 MYH9
glycogen granule 1 PPP1R3D


文献列表

  • Alena A Semenova, Victor N Samartsev, Mikhail V Dubinin. The stimulation of succinate-fueled respiration of rat liver mitochondria in state 4 by α,ω-hexadecanedioic acid without induction of proton conductivity of the inner membrane. Intrinsic uncoupling of the bc1 complex. Biochimie. 2021 Feb; 181(?):215-225. doi: 10.1016/j.biochi.2020.12.021. [PMID: 33400934]
  • Rasa Santockyte, Hamza Kandoussi, Weiqi Chen, Naiyu Zheng, Lata Venkatarangan, Jinping Gan, Hong Shen, Samuel J Bonacorsi, John Easter, Richard Burrell, Yan J Zhang, Jianing Zeng. LC-MS/MS bioanalysis of plasma 1, 14-tetradecanedioic acid and 1, 16-hexadecanedioic acid as candidate biomarkers for organic anion-transporting polypeptide mediated drug-drug interactions. Bioanalysis. 2018 Sep; 10(18):1473-1485. doi: 10.4155/bio-2018-0170. [PMID: 30215261]
  • Hong Shen, Weiqi Chen, Dieter M Drexler, Sandhya Mandlekar, Vinay K Holenarsipur, Eric E Shields, Robert Langish, Kurex Sidik, Jinping Gan, W Griffith Humphreys, Punit Marathe, Yurong Lai. Comparative Evaluation of Plasma Bile Acids, Dehydroepiandrosterone Sulfate, Hexadecanedioate, and Tetradecanedioate with Coproporphyrins I and III as Markers of OATP Inhibition in Healthy Subjects. Drug metabolism and disposition: the biological fate of chemicals. 2017 08; 45(8):908-919. doi: 10.1124/dmd.117.075531. [PMID: 28576766]
  • S W Yee, M M Giacomini, C-H Hsueh, D Weitz, X Liang, S Goswami, J M Kinchen, A Coelho, A A Zur, K Mertsch, W Brian, D L Kroetz, K M Giacomini. Metabolomic and Genome-wide Association Studies Reveal Potential Endogenous Biomarkers for OATP1B1. Clinical pharmacology and therapeutics. 2016 Nov; 100(5):524-536. doi: 10.1002/cpt.434. [PMID: 27447836]
  • Aleksander A Vedernikov, Mikhail V Dubinin, Vladimir A Zabiakin, Victor N Samartsev. Ca(2+)-dependent nonspecific permeability of the inner membrane of liver mitochondria in the guinea fowl (Numida meleagris). Journal of bioenergetics and biomembranes. 2015 Jun; 47(3):235-42. doi: 10.1007/s10863-015-9606-z. [PMID: 25690874]
  • Hui Li, Franck Pinot, Vincent Sauveplane, Danièle Werck-Reichhart, Patrik Diehl, Lukas Schreiber, Rochus Franke, Ping Zhang, Liang Chen, Yawei Gao, Wanqi Liang, Dabing Zhang. Cytochrome P450 family member CYP704B2 catalyzes the {omega}-hydroxylation of fatty acids and is required for anther cutin biosynthesis and pollen exine formation in rice. The Plant cell. 2010 Jan; 22(1):173-90. doi: 10.1105/tpc.109.070326. [PMID: 20086189]
  • Clark J Nelson, Jessica P Otis, Sandra L Martin, Hannah V Carey. Analysis of the hibernation cycle using LC-MS-based metabolomics in ground squirrel liver. Physiological genomics. 2009 Mar; 37(1):43-51. doi: 10.1152/physiolgenomics.90323.2008. [PMID: 19106184]
  • Vukic Soskic, Gerhard Schwall, Elke Nyakatura, Slobodan Poznanovic, Werner Stegmann, Andre Schrattenholz. Hexadecanedionic acid-sepharose 4B: A new tool for preparation of albumin-depleted plasma. Journal of proteome research. 2006 Dec; 5(12):3453-8. doi: 10.1021/pr060387q. [PMID: 17137348]
  • Gustavo Bonaventure, Frédéric Beisson, John Ohlrogge, Mike Pollard. Analysis of the aliphatic monomer composition of polyesters associated with Arabidopsis epidermis: occurrence of octadeca-cis-6, cis-9-diene-1,18-dioate as the major component. The Plant journal : for cell and molecular biology. 2004 Dec; 40(6):920-30. doi: 10.1111/j.1365-313x.2004.02258.x. [PMID: 15584957]
  • Jean-Paul Douliez. Cutin and suberin monomers are membrane perturbants. Journal of colloid and interface science. 2004 Mar; 271(2):507-10. doi: 10.1016/j.jcis.2003.12.020. [PMID: 14972629]
  • Ahmed I Rushdi, Bernd R T Simoneit. Condensation reactions and formation of amides, esters, and nitriles under hydrothermal conditions. Astrobiology. 2004; 4(2):211-24. doi: 10.1089/153110704323175151. [PMID: 15253839]
  • Takako Tazawa, Huai-Qing Zhao, Yan Li, Meselhy Ragab Meselhy, Norio Nakamura, Teruaki Akao, Masao Hattori. A new enzyme immunoassay for aconitine and its application to quantitative determination of aconitine levels in plasma. Biological & pharmaceutical bulletin. 2003 Sep; 26(9):1289-94. doi: 10.1248/bpb.26.1289. [PMID: 12951473]
  • A Aarsland, N Aarsaether, J Bremer, R K Berge. Alkylthioacetic acids (3-thia fatty acids) as non-beta-oxidizable fatty acid analogues: a new group of hypolipidemic drugs. III. Dissociation of cholesterol- and triglyceride-lowering effects and the induction of peroxisomal beta-oxidation. Journal of lipid research. 1989 Nov; 30(11):1711-8. doi: . [PMID: 2614273]