Undecylenic acid (BioDeep_00000003500)

Main id: BioDeep_00000009603

Secondary id: BioDeep_00000863430

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Zinc undecylenate (undecylenic acid)

化学式: C11H20O2 (184.1463)
中文名称: 十一烯酸, 十一碳烯酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(=C)CCCCCCCCC(=O)O
InChI: InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)

描述信息

Undecylenic acid, also known as 10-undecylenate or omega-undecenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecylenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient and is a sweet and woody-tasting compound. Undecylenic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID:31477923). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. Undecylenic acid is used in the production of the bioplastic Nylon-11, in the treatment of fungal infections in the skin, and as a precursor in the manufacture of a wide assortment of pharmaceuticals, cosmetics, perfumes, and personal hygiene products.
D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use
Flavouring ingredient. Undecylenic acid is found in black elderberry.
C254 - Anti-Infective Agent > C514 - Antifungal Agent
Same as: D02159
10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.
10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.

同义名列表

48 个代谢物同义名

Zinc undecylenate (undecylenic acid); N-UNDECYLENIC ACID (10-1); Omega-hendecenoic acid; Undecylenic acid, usan; Acide 10-undecanoique; Omega-undecenoic acid; Acido 10-undecenoico; Acide 10-undecylique; 10-Henedecenoic acid; Undecyl-10-enic acid; 10-hendecenoic acid; 10-undecylenic acid; Undec-10-enoic acid; 10-Undecenoic acid; Undecylenenic acid; 9-undecylenic acid; N-Undecylenic acid; Omega-hendecenoate; ω-Hendecenoic acid; Undecylenic acids; 9-undecenoic acid; Undecen-10-saeure; Undecen-10-acid-1; ω-Undecenoic acid; Omega-undecenoate; 10-Undecensaeure; Undecelinic acid; undecylenic acid; undecenoic acid; 10-Hendecenoate; 10-Undecylenate; 10-Undecenoate; 10-Hendecenoic; Undecelinate; Undecylenate; Mycodermine; Undecenoate; FEMA 3247; C11:1n-1; Renselin; Sevinon; FA 11:1; Desenex; Declid; Cruex; Undecylenic acid; Undecylenic acid; Undecylenic acid



数据库引用编号

23 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)

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 10 AIMP2, ALB, BGLAP, CAPN1, CASP3, MAPK8, NFATC1, NFKB1, NPM1, PPARG
Peripheral membrane protein 2 GORASP1, SLC27A2
Endoplasmic reticulum membrane 1 SLC27A2
Nucleus 9 AIMP2, ALB, CASP3, JUND, MAPK8, NFATC1, NFKB1, NPM1, PPARG
cytosol 11 AIMP2, ALB, CAPN1, CASP3, LIPE, MAPK8, NFATC1, NFKB1, NPM1, PPARG, SLC27A2
dendrite 1 BGLAP
nuclear body 1 NFATC1
centrosome 2 ALB, NPM1
nucleoplasm 7 CASP3, JUND, MAPK8, NFATC1, NFKB1, NPM1, PPARG
RNA polymerase II transcription regulator complex 2 JUND, PPARG
Cell membrane 5 CAPN1, CD86, CLEC4D, LIPE, SLC27A2
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 1 SLC27A2
Golgi apparatus membrane 1 GORASP1
Synapse 1 MAPK8
cell surface 1 CD86
glutamatergic synapse 1 CASP3
Golgi apparatus 2 ALB, GORASP1
Golgi membrane 2 GORASP1, INS
neuronal cell body 1 CASP3
Cytoplasm, cytosol 2 AIMP2, LIPE
Lysosome 1 CAPN1
plasma membrane 4 CAPN1, CD86, CLEC4D, SLC27A2
Membrane 7 AIMP2, CAPN1, CD86, CLEC4D, LIPE, NPM1, SLC27A2
axon 1 MAPK8
caveola 1 LIPE
extracellular exosome 4 ALB, CAPN1, CD86, SLC27A2
endoplasmic reticulum 1 ALB
extracellular space 6 ALB, BGLAP, IL10, IL4, INS, PYY3
perinuclear region of cytoplasm 2 NFATC1, PPARG
mitochondrion 2 CAPN1, NFKB1
protein-containing complex 2 ALB, NPM1
intracellular membrane-bounded organelle 1 PPARG
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 CD86
Secreted 6 ALB, BGLAP, IL10, IL4, INS, PYY3
extracellular region 7 ALB, BGLAP, CAPN1, IL10, IL4, INS, NFKB1
anchoring junction 1 ALB
transcription regulator complex 3 JUND, NFATC1, NFKB1
centriolar satellite 1 CD86
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NPM1
external side of plasma membrane 2 CD86, CLEC4D
perikaryon 1 BGLAP
nucleolus 1 NPM1
sarcoplasm 1 NFATC1
Single-pass type II membrane protein 1 CLEC4D
vesicle 1 BGLAP
focal adhesion 2 CAPN1, NPM1
cis-Golgi network 1 GORASP1
peroxisomal membrane 1 SLC27A2
receptor complex 1 PPARG
ciliary basal body 1 ALB
chromatin 4 JUND, NFATC1, NFKB1, PPARG
centriole 1 ALB
Nucleus, nucleolus 1 NPM1
spindle pole 1 ALB
blood microparticle 1 ALB
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Cornified envelope 1 CAPN1
Nucleus, nucleoplasm 1 NPM1
specific granule membrane 2 CLEC4D, SLC27A2
tertiary granule membrane 1 CLEC4D
Peroxisome membrane 1 SLC27A2
Microsome 1 SLC27A2
ficolin-1-rich granule lumen 1 CAPN1
secretory granule lumen 2 INS, NFKB1
Golgi lumen 2 BGLAP, INS
endoplasmic reticulum lumen 4 ALB, BGLAP, INS, SLC27A2
transcription repressor complex 1 JUND
platelet alpha granule lumen 1 ALB
specific granule lumen 1 NFKB1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
spindle pole centrosome 1 NPM1
ribonucleoprotein complex 1 NPM1
protein-DNA complex 1 NPM1
ficolin-1-rich granule membrane 1 CLEC4D
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
granular component 1 NPM1
transcription factor AP-1 complex 1 JUND
calpain complex 1 CAPN1
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
ciliary transition fiber 1 ALB


文献列表

  • Chao Fan, Bei Liu, Hui Li, Kaijun Quan, Jia Chen, Hongdeng Qiu. N-Vinyl pyrrolidone and undecylenic acid copolymerized on silica surface as mixed-mode stationary phases for reversed-phase and hydrophilic interaction chromatography. Journal of chromatography. A. 2021 Oct; 1655(?):462534. doi: 10.1016/j.chroma.2021.462534. [PMID: 34509123]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Yasemin Sezgin, Mehtap Bilgin Çetin, Şule Bulut, Nilgün Özlem Alptekin, Pelin Börçek. Evaluating the Effects of a Topical Preparation with Dexpanthenol, Silbiol, Undecylenic Acid, and Lidocaine on Palatal Mucosa Wound Healing in a Rat Model. Balkan medical journal. 2019 02; 36(2):88-95. doi: 10.4274/balkanmedj.galenos.2018.2018.0167. [PMID: 30322831]
  • Joanne Heade, Sam Maher, Sinead B Bleiel, David J Brayden. Labrasol® and Salts of Medium-Chain Fatty Acids Can Be Combined in Low Concentrations to Increase the Permeability of a Macromolecule Marker Across Isolated Rat Intestinal Mucosae. Journal of pharmaceutical sciences. 2018 06; 107(6):1648-1655. doi: 10.1016/j.xphs.2018.02.012. [PMID: 29462634]
  • Gorla Geethanjali, Korlipara V Padmaja, Arukali Sammaiah, Rachapudi B N Prasad. Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives. Journal of agricultural and food chemistry. 2014 Nov; 62(47):11505-11. doi: 10.1021/jf5033558. [PMID: 25369173]
  • David J Brayden, Edwin Walsh. Efficacious intestinal permeation enhancement induced by the sodium salt of 10-undecylenic acid, a medium chain fatty acid derivative. The AAPS journal. 2014 Sep; 16(5):1064-76. doi: 10.1208/s12248-014-9634-3. [PMID: 24961919]
  • T Vijai Kumar Reddy, B L A Prabhavathi Devi, R B N Prasad, M Poornima, C Ganesh Kumar. Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol. Bioorganic & medicinal chemistry letters. 2012 Jul; 22(14):4678-80. doi: 10.1016/j.bmcl.2012.05.082. [PMID: 22704888]
  • Miia Kovalainen, Juha Mönkäre, Ermei Mäkilä, Jarno Salonen, Vesa-Pekka Lehto, Karl-Heinz Herzig, Kristiina Järvinen. Mesoporous silicon (PSi) for sustained peptide delivery: effect of psi microparticle surface chemistry on peptide YY3-36 release. Pharmaceutical research. 2012 Mar; 29(3):837-46. doi: 10.1007/s11095-011-0611-6. [PMID: 22033881]
  • Marijke Van der Steen, Christian V Stevens. Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. ChemSusChem. 2009; 2(8):692-713. doi: 10.1002/cssc.200900075. [PMID: 19650106]
  • Xing-Cong Li, Melissa R Jacob, Shabana I Khan, M Khalid Ashfaq, K Suresh Babu, Ameeta K Agarwal, Hala N Elsohly, Susan P Manly, Alice M Clark. Potent in vitro antifungal activities of naturally occurring acetylenic acids. Antimicrobial agents and chemotherapy. 2008 Jul; 52(7):2442-8. doi: 10.1128/aac.01297-07. [PMID: 18458131]
  • R Kreiling, H M Hollnagel, L Hareng, D Eigler, M S Lee, P Griem, B Dreessen, M Kleber, A Albrecht, C Garcia, A Wendel. Comparison of the skin sensitizing potential of unsaturated compounds as assessed by the murine local lymph node assay (LLNA) and the guinea pig maximization test (GPMT). Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Jun; 46(6):1896-904. doi: 10.1016/j.fct.2008.01.019. [PMID: 18343554]
  • Danai Malli, Evagelos Gikas, Andreas Vavagiannis, Michael Kazanis, Konstantinos Daniilides, Dimitra Gennimata, Irene Panderi. Determination of nateglinide in human plasma by high-performance liquid chromatography with pre-column derivatization using a coumarin-type fluorescent reagent. Analytica chimica acta. 2007 Sep; 599(1):143-50. doi: 10.1016/j.aca.2007.08.004. [PMID: 17765074]
  • P Christiaens, V Vermeeren, S Wenmackers, M Daenen, K Haenen, M Nesládek, M vandeVen, M Ameloot, L Michiels, P Wagner. EDC-mediated DNA attachment to nanocrystalline CVD diamond films. Biosensors & bioelectronics. 2006 Aug; 22(2):170-7. doi: 10.1016/j.bios.2005.12.013. [PMID: 16442276]
  • A C Buck. Disorders of micturition in bacterial prostatitis. Proceedings of the Royal Society of Medicine. 1975 Aug; 68(8):508-11. doi: NULL. [PMID: 681]
  • T Fukushima. [Monoamine oxidase (XXXVI). Characteristics of benzylamine oxidase in the dog serum]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 1975 Jul; 71(5):457-62. doi: . [PMID: 280]