Caproic acid (BioDeep_00000002191)

 

Secondary id: BioDeep_00000229603, BioDeep_00000405296, BioDeep_00000405855, BioDeep_00000861084, BioDeep_00000872171

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


Hexanoic acid, sodium salt, 1-(11)C-labeled

化学式: C6H12O2 (116.0837)
中文名称: 己酸-1,2-13C2, 己酸, 正己酸
谱图信息: 最多检出来源 Homo sapiens(blood) 55.38%

分子结构信息

SMILES: C(=O)(O)CCCCC
InChI: InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

描述信息

Caproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15\\% of the fat in goats milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230).
Present in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient
KEIO_ID C035

同义名列表

55 个代谢物同义名

Hexanoic acid, sodium salt, 1-(11)C-labeled; Hexanoic acid, manganese (2+) salt; Hexanoic acid, sodium salt (1:1); Hexanoic acid, rhodium (2+) salt; Hexanoic acid, copper (2+) salt; Hexanoic acid, nickel (2+) salt; Hexanoic acid, potassium salt; Hexanoic acid, calcium salt; Hexanoic acid, sodium salt; Hexanoic acid, barium salt; Caproic acid sodium salt; 1-Pentanecarboxylic acid; Pentanecarboxylic acid; Bismuth(III)hexanoate; 1-Pentanecarboxylate; Calcium N-hexanoate; Pentanecarboxylate; Calcium hexanoate; Pentylformic acid; Butylacetic acid; Sodium capronate; Sodium hexanoate; Pentiformic acid; 1-Hexanoic acid; Sodium caproate; n-Hexanoic acid; CH3-[CH2]4-COOH; N-Caproic acid; N-Hexylic acid; Capronic acid; HEXANOIC ACID; N-Hexoic acid; Pentylformate; Caproic acid; Pentiformate; Hexylic acid; Butylacetate; 1-Hexanoate; N-Hexanoate; Hexoic acid; N-Hexylate; N-Caproate; Capronate; Bi(ohex)3; N-Hexoate; Hexanoate; Caproate; Hexylate; FA(6:0); Hexoate; C6:0; 6:0; Hexanoic acid; Hexanoic acid; Hexanoic acid



数据库引用编号

33 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

18 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(18)

PharmGKB(0)

59 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 AKT1, ALB, CAT, CYP2B6, FASN, MTOR, TXN, TYR
Peripheral membrane protein 4 ACHE, CYP2B6, MBP, MTOR
Endoplasmic reticulum membrane 4 CD4, CYP2B6, HSP90B1, MTOR
Nucleus 9 ACHE, AKT1, ALB, CALB1, HSP90B1, MBP, MTOR, PPARA, TXN
cytosol 10 AKT1, ALB, CALB1, CAT, FASN, HSP90B1, LIPE, MBP, MTOR, TXN
dendrite 2 CALB1, MTOR
phagocytic vesicle 1 MTOR
centrosome 1 ALB
nucleoplasm 4 AKT1, MTOR, PPARA, TXN
Cell membrane 5 ACHE, AKT1, CD4, LIPE, TNF
Cytoplasmic side 2 MBP, MTOR
lamellipodium 1 AKT1
Golgi apparatus membrane 1 MTOR
Synapse 3 ACHE, CALB1, MBP
cell cortex 1 AKT1
cell surface 3 ACHE, MBP, TNF
glutamatergic synapse 2 AKT1, CALB1
Golgi apparatus 4 ACHE, ALB, ATRN, FASN
Golgi membrane 2 INS, MTOR
lysosomal membrane 1 MTOR
neuromuscular junction 1 ACHE
neuronal cell body 3 CALB1, MBP, TNF
postsynapse 1 AKT1
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 LIPE
Lysosome 2 MTOR, TYR
plasma membrane 7 ACHE, AKT1, ATRN, CD4, FASN, MBP, TNF
terminal bouton 1 CALB1
Membrane 7 ACHE, AKT1, CAT, FASN, HSP90B1, LIPE, MTOR
axon 1 CALB1
caveola 1 LIPE
extracellular exosome 8 ALB, ATRN, CALB1, CAT, FASN, HSP90B1, MBP, TXN
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 ALB, HSP90B1
extracellular space 7 ACHE, ALB, ATRN, CXCL8, IL6, INS, TNF
perinuclear region of cytoplasm 3 ACHE, HSP90B1, TYR
mitochondrion 1 CAT
protein-containing complex 5 AKT1, ALB, CAT, HSP90B1, MBP
intracellular membrane-bounded organelle 3 CAT, CYP2B6, TYR
Microsome membrane 2 CYP2B6, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 3 ATRN, CD4, TYR
Secreted 6 ACHE, ALB, CXCL8, IL6, INS, TXN
extracellular region 10 ACHE, ALB, CAT, CXCL8, HSP90B1, IL6, INS, MBP, TNF, TXN
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
hippocampal mossy fiber to CA3 synapse 1 CALB1
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 1 CAT
Extracellular side 1 ACHE
anchoring junction 1 ALB
external side of plasma membrane 2 CD4, TNF
dendritic spine 1 CALB1
microtubule cytoskeleton 1 AKT1
Melanosome membrane 1 TYR
midbody 1 HSP90B1
Early endosome 1 CD4
cell-cell junction 1 AKT1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Membrane raft 2 CD4, TNF
focal adhesion 2 CAT, HSP90B1
spindle 1 AKT1
GABA-ergic synapse 1 CALB1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 2 HSP90B1, MBP
ciliary basal body 2 AKT1, ALB
chromatin 1 PPARA
phagocytic cup 1 TNF
cell periphery 1 MBP
[Isoform 3]: Nucleus 1 MBP
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
stereocilium 1 CALB1
Melanosome 3 FASN, HSP90B1, TYR
side of membrane 1 ACHE
myelin sheath 1 MBP
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 2 CAT, MBP
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 5 ALB, CD4, HSP90B1, IL6, INS
platelet alpha granule lumen 1 ALB
transport vesicle 2 INS, MBP
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
calyx of Held 1 CALB1
clathrin-coated endocytic vesicle membrane 1 CD4
Sarcoplasmic reticulum lumen 1 HSP90B1
synaptic cleft 1 ACHE
[Isoform 1]: Cell membrane 1 ATRN
postsynaptic cytosol 1 CALB1
Cytoplasmic vesicle, phagosome 1 MTOR
cuticular plate 1 CALB1
presynaptic cytosol 1 CALB1
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
compact myelin 1 MBP
internode region of axon 1 MBP
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 HSP90B1
[Bone marrow proteoglycan]: Secreted 1 MBP
[Isoform H]: Cell membrane 1 ACHE
glycogen granule 1 FASN
ciliary transition fiber 1 ALB
Myelin membrane 1 MBP
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Rikard Fristedt, Vanessa Ruppert, Tania Trower, Janine Cooney, Rikard Landberg. Quantitation of circulating short-chain fatty acids in small volume blood samples from animals and humans. Talanta. 2024 May; 272(?):125743. doi: 10.1016/j.talanta.2024.125743. [PMID: 38382298]
  • Huiqin Shi, Wei Li, Hongyu Chen, Yao Meng, Huifang Wu, Jian Wang, Shuo Shen. Synthetic Microbial Community Members Interact to Metabolize Caproic Acid to Inhibit Potato Dry Rot Disease. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084437. [PMID: 38674022]
  • Sergio Morales-Palomo, Clara Navarrete, José Luis Martínez, Cristina González-Fernández, Elia Tomás-Pejó. Transcriptomic profiling of an evolved Yarrowia lipolytica strain: tackling hexanoic acid fermentation to increase lipid production from short-chain fatty acids. Microbial cell factories. 2024 Apr; 23(1):101. doi: 10.1186/s12934-024-02367-4. [PMID: 38566056]
  • Yiming Ni, Liangyin Cai, Xiaojun Gou, Wenjie Li, Mingmei Zhou, Ying Huang. Therapeutic effect of Sanhua decoction on rats with middle cerebral artery occlusion and the associated changes in gut microbiota and short-chain fatty acids. PloS one. 2024; 19(2):e0298148. doi: 10.1371/journal.pone.0298148. [PMID: 38363776]
  • Hongbo Yuan, Bingke Shi, Zhuoni Wang, Genhong Qin, Hui Hou, Hongtao Tu, Li Wang. Exploration of the Biocontrol Activity of Bacillus atrophaeus Strain HF1 against Pear Valsa Canker Caused by Valsa pyri. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015477. [PMID: 37895155]
  • Valentino Casolo, Marco Zancani, Elisa Pellegrini, Antonio Filippi, Sara Gargiulo, Dennis Konnerup, Piero Morandini, Ole Pedersen. Restricted O2 consumption in pea roots induced by hexanoic acid is linked to depletion of Krebs cycle substrates. Physiologia plantarum. 2023 Sep; 175(5):e14024. doi: 10.1111/ppl.14024. [PMID: 37882315]
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  • Tinh Van Nguyen, Tomeu Viver, Ilse Smets, Kristel Bernaerts, Karoline Faust, Rob Lavigne, Laurent Poughon, Claude-Gilles Dussap, Dirk Springael. Thermocaproicibacter melissae gen. nov., sp. nov., a thermophilic chain-elongating bacterium, producing n-caproate from polymeric carbohydrates. International journal of systematic and evolutionary microbiology. 2023 May; 73(5):. doi: 10.1099/ijsem.0.005893. [PMID: 37200213]
  • Ying He, Bang Cheng, Bing-Jian Guo, Zheng Huang, Jing-Hua Qin, Qian-Yi Wang, Lin-Lin Feng, Yun-Yuan Nong, Dan Zhu, Hong-Wei Guo, Zhi-Heng Su. Metabonomics and 16S rRNA gene sequencing to study the therapeutic mechanism of Danggui Sini decoction on collagen-induced rheumatoid arthritis rats with Cold Bi syndrome. Journal of pharmaceutical and biomedical analysis. 2023 Jan; 222(?):115109. doi: 10.1016/j.jpba.2022.115109. [PMID: 36270097]
  • Chongrong Shen, Yanru Chen, Qiaoling Wang, Yingkai Sun, Huibin Lin, Mengshan Ni, Yufei Chen, Ling Zhang, Jiabin Jin, Xiayang Ying, Yuyao Zou, Xiaolin Wang, Yaorui Ye, Miaomiao Yuan, Nan Yin, Zhiwen Cao, Yifei Zhang, Weiqiong Gu, Weiqing Wang, Guang Ning, Jiqiu Wang, Shaoqian Zhao, Jie Hong, Ruixin Liu. Fecal short chain fatty acids modify therapeutic effects of sleeve gastrectomy. Frontiers in endocrinology. 2023; 14(?):1277035. doi: 10.3389/fendo.2023.1277035. [PMID: 38027127]
  • Zachary A Drum, Stephen M Lanno, Sara M Gregory, Serena J Shimshak, Mukshud Ahamed, Will Barr, Bethlehem Bekele, Alison Biester, Colleen Castro, Lauren Connolly, Nicole DelGaudio, William Humphrey, Helen Karimi, Sophie Karolczak, Tay-Shaun Lawrence, Andrew McCracken, Noah Miller-Medzon, Leah Murphy, Cameron Park, Sojeong Park, Chloe Qiu, Kevin Serra, Gigi Snyder, Alexa Strauss, Spencer Tang, Christina Vyzas, Joseph D Coolon. Genomics analysis of hexanoic acid exposure in Drosophila species. G3 (Bethesda, Md.). 2022 01; 12(1):. doi: 10.1093/g3journal/jkab354. [PMID: 34718544]
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