16-Hydroxyhexadecanoic acid (BioDeep_00000002135)

 

Secondary id: BioDeep_00000265023

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


16-hydroxyhexadecanoic acid

化学式: C16H32O3 (272.2351)
中文名称: 16-羟基十六酸, 16-羟基棕榈酸
谱图信息: 最多检出来源 Homo sapiens(plant) 15.48%

Reviewed

Last reviewed on 2024-10-09.

Cite this Page

16-Hydroxyhexadecanoic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/16-hydroxyhexadecanoic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002135). 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)CCCCCCCO
InChI: InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)

描述信息

16-Hydroxyhexadecanoic acid, also known as 16-hydroxypalmitic acid, is a hydroxylated fatty acid where the terminal (omega) carbon has been hydroxylated. In animal tissues, a family of enzymes termed cytochromes P450s are involved in fatty acid oxidation, hydroxylating with high specificity at the energetically unfavourable terminal (omega) or omega-1 carbons. Hydroxy fatty acids primarily come from the consumption of plant products (vegetables or fruits) or cow’s milk. Omega hydroxy fatty acids are found in the structure of suberin, a lipid polyester present in plant cell walls, and of cutin, a lipid polyester which is a component of the plant cuticle. These apoplastic structures are important plant-environment interfaces that act as barriers limiting water and nutrient loss and protecting plants from radiation and pathogens. 16-Hydroxyhexadecanoic acid and 18-hydroxystearic acid are particularly abundant in cutin in the plant cuticle. 16-Hydroxyhexadecanoic acid has been proposed as a biomarker of beer consumption.
16-hydroxy-hexadecanoic acid, also known as 16-hydroxypalmitic acid or 16-oh 16:0, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 16-hydroxy-hexadecanoic acid is considered to be a fatty acid lipid molecule. 16-hydroxy-hexadecanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 16-hydroxy-hexadecanoic acid can be synthesized from hexadecanoic acid. 16-hydroxy-hexadecanoic acid is also a parent compound for other transformation products, including but not limited to, (3R)-3,16-dihydroxypalmitic acid, oscr#28, and 16-hydroxyhexadecanoyl-CoA. 16-hydroxy-hexadecanoic acid can be found in a number of food items such as other cereal product, hyacinth bean, red rice, and elliotts blueberry, which makes 16-hydroxy-hexadecanoic acid a potential biomarker for the consumption of these food products.

同义名列表

30 个代谢物同义名

omega hydroxy hexadecanoate (n-C16:0); omega-hydroxy hexadecanoic acid; omega hydroxy hexadecanoic acid; Omega-hydroxyhexadecanoic acid; 16-Hydroxy-hexadecanoic acid; 16-hydroxy hexadecanoic acid; 16-Hydoxy hexadecanoic acid; omega hydroxy hexadecanoate; 16-Hydroxyhexadecanoic acid; omega-hydroxy hexadecanoate; w-hydroxy hexadecanoic acid; Ω-hydroxyhexadecanoic acid; Omega-hydroxypalmitic acid; hydroxy hexadecanoic acid; 16-Hydroxy-hexadecanoate; 16-Hydroxy hexadecanoate; 16-Hydroxyhexadecanoate; 16-Hydoxy hexadecanoate; w-hydroxy hexadecanoate; 16-hydroxypalmitic acid; Ω-hydroxypalmitic acid; Omega-hydroxypalmitate; hydroxy hexadecanoate; 16-Hydroxypalmitate; Lanopalmitic acid; FA(16:0(16-OH)); Juniperic acid; Juniperate; 16-OH 16:0; 16-Hydroxypalmitate



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)

35 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 C1orf116, CALM1, CALM3, CASP3, FADD, FASN, GRP, GYG1
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 2 CYP1B1, SCD
Nucleus 5 CALM1, CALM3, CASP3, GYG1, MYB
cytosol 9 C1orf116, CALM1, CASP3, FADD, FASN, GYG1, LIPE, MYB, SHARPIN
dendrite 1 SHARPIN
centrosome 2 CALM1, CALM3
nucleoplasm 3 CALM1, CASP3, MYB
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 1 LIPE
Multi-pass membrane protein 2 MCU, SCD
Synapse 1 SHARPIN
cell surface 1 ICAM1
glutamatergic synapse 2 CASP3, SHARPIN
Golgi apparatus 1 FASN
mitochondrial inner membrane 1 MCU
neuronal cell body 1 CASP3
Cytoplasm, cytosol 2 LIPE, SHARPIN
plasma membrane 8 C1orf116, CALM1, CALM3, FADD, FASN, ICAM1, ME2, ME3
Membrane 11 CUTA, CYP1B1, FASN, GYG1, ICAM1, LIPE, MCU, ME2, ME3, MYB, SCD
caveola 1 LIPE
extracellular exosome 5 C1orf116, CPVL, CUTA, FASN, ICAM1
endoplasmic reticulum 1 SCD
extracellular space 3 GRP, ICAM1, IL6
lysosomal lumen 1 GYG1
mitochondrion 5 CUTA, CYP1B1, MCU, ME2, ME3
protein-containing complex 2 CALM1, CALM3
intracellular membrane-bounded organelle 2 CYP1B1, ME2
Microsome membrane 1 CYP1B1
postsynaptic density 2 CASP3, SHARPIN
Single-pass type I membrane protein 1 ICAM1
Secreted 2 GRP, IL6
extracellular region 4 CALM1, GRP, GYG1, IL6
cytoplasmic side of plasma membrane 1 FADD
Single-pass membrane protein 2 ME2, ME3
Mitochondrion matrix 1 ME2
mitochondrial matrix 2 ME2, ME3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CALM1, CALM3
external side of plasma membrane 1 ICAM1
Secreted, extracellular space, extracellular matrix 1 GRP
nucleolus 1 SCD
vesicle 2 CALM1, CALM3
Mitochondrion inner membrane 1 MCU
Membrane raft 1 ICAM1
Cytoplasm, cytoskeleton, spindle 2 CALM1, CALM3
focal adhesion 1 ICAM1
extracellular matrix 1 GRP
collagen-containing extracellular matrix 1 ICAM1
sarcomere 2 CALM1, CALM3
Cell projection, neuron projection 1 GRP
neuron projection 1 GRP
spindle pole 2 CALM1, CALM3
Cell projection, cilium, flagellum 1 CALM1
sperm midpiece 2 CALM1, CALM3
Cytoplasm, cytoskeleton, spindle pole 2 CALM1, CALM3
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Melanosome 1 FASN
cell body 1 FADD
myelin sheath 2 CALM1, CALM3
voltage-gated potassium channel complex 2 CALM1, CALM3
ficolin-1-rich granule lumen 1 GYG1
secretory granule lumen 2 GRP, GYG1
endoplasmic reticulum lumen 1 IL6
nuclear matrix 1 MYB
immunological synapse 1 ICAM1
neuronal dense core vesicle 1 GRP
calyx of Held 2 CALM1, CALM3
calcium channel complex 3 CALM1, CALM3, MCU
spindle microtubule 2 CALM1, CALM3
CD95 death-inducing signaling complex 1 FADD
death-inducing signaling complex 2 CASP3, FADD
ripoptosome 1 FADD
presynaptic cytosol 2 CALM1, CALM3
Cytoplasmic vesicle, secretory vesicle lumen 1 GRP
catalytic complex 2 CALM1, CALM3
interleukin-6 receptor complex 1 IL6
glycogen granule 1 FASN
uniplex complex 1 MCU
LUBAC complex 1 SHARPIN


文献列表

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  • Burkhardt S Schuett, Thomas J Millar. An investigation of the likely role of (O-acyl) ω-hydroxy fatty acids in meibomian lipid films using (O-oleyl) ω-hydroxy palmitic acid as a model. Experimental eye research. 2013 Oct; 115(?):57-64. doi: 10.1016/j.exer.2013.06.016. [PMID: 23792170]
  • Alfonso Fernández-Álvarez, Miriam Marín-Menguiano, Daniel Lanver, Alberto Jiménez-Martín, Alberto Elías-Villalobos, Antonio J Pérez-Pulido, Regine Kahmann, José I Ibeas. Identification of O-mannosylated virulence factors in Ustilago maydis. PLoS pathogens. 2012; 8(3):e1002563. doi: 10.1371/journal.ppat.1002563. [PMID: 22416226]
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  • Anne-Laure Fameau, Bérénice Houinsou-Houssou, Jorge Luis Ventureira, Laurence Navailles, Frédéric Nallet, Bruno Novales, Jean-Paul Douliez. Self-assembly, foaming, and emulsifying properties of sodium alkyl carboxylate/guanidine hydrochloride aqueous mixtures. Langmuir : the ACS journal of surfaces and colloids. 2011 Apr; 27(8):4505-13. doi: 10.1021/la2002404. [PMID: 21405069]
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  • Katrien Curvers, Hamed Seifi, Grégory Mouille, Riet de Rycke, Bob Asselbergh, Annelies Van Hecke, Dieter Vanderschaeghe, Herman Höfte, Nico Callewaert, Frank Van Breusegem, Monica Höfte. Abscisic acid deficiency causes changes in cuticle permeability and pectin composition that influence tomato resistance to Botrytis cinerea. Plant physiology. 2010 Oct; 154(2):847-60. doi: 10.1104/pp.110.158972. [PMID: 20709830]
  • Anna A Dobritsa, Zhentian Lei, Shuh-Ichi Nishikawa, Ewa Urbanczyk-Wochniak, David V Huhman, Daphne Preuss, Lloyd W Sumner. LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis. Plant physiology. 2010 Jul; 153(3):937-55. doi: 10.1104/pp.110.157446. [PMID: 20442277]
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  • Judy Schnurr, Jay Shockey, John Browse. The acyl-CoA synthetase encoded by LACS2 is essential for normal cuticle development in Arabidopsis. The Plant cell. 2004 Mar; 16(3):629-42. doi: 10.1105/tpc.017608. [PMID: 14973169]
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