Chimyl alcohol (BioDeep_00000009625)

   

natural product


代谢物信息卡片


1-O-HEXADECYL-RAC-GLYCEROL

化学式: C19H40O3 (316.2977)
中文名称: 1-O-十六烷基-sn -甘油(HG), 鲛肝醇
谱图信息: 最多检出来源 Homo sapiens(plant) 5.43%

分子结构信息

SMILES: CCCCCCCCCCCCCCCCOCC(CO)O
InChI: InChI=1S/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3

描述信息

同义名列表

9 个代谢物同义名

1-O-HEXADECYL-RAC-GLYCEROL; 1-O-Hexadecyl-sn-glycerol; Glycerol hexadecyl ether; 1-O-Hexadecylglycerol; 1-Hexadecylglycerol; MG(O-16:0/0:0/0:0); Chimyl alcohol; MG(O-16:0); MG O-16:0



数据库引用编号

17 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)

18 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 3 DLK1, PTGS2, SRARP
Peripheral membrane protein 5 GNPAT, HSD17B6, LPL, MBP, PTGS2
Endoplasmic reticulum membrane 3 AGMO, HSP90B1, PTGS2
Nucleus 5 GABPA, HSP90B1, MBP, PDIA3, SRARP
cytosol 5 GNPAT, HSP90B1, LIPE, MBP, PRKCQ
mitochondrial membrane 1 GNPAT
phagocytic vesicle 1 PDIA3
nucleoplasm 1 GABPA
Cell membrane 3 CD86, LIPE, LPL
Cytoplasmic side 1 MBP
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 AGMO
Golgi apparatus membrane 1 A4GALT
Synapse 1 MBP
cell surface 4 CD86, LPL, MBP, PDIA3
Golgi membrane 1 A4GALT
neuronal cell body 1 MBP
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 LIPE
plasma membrane 6 CD86, F2, KNG1, LPL, MBP, PRKCQ
Membrane 7 A4GALT, AGMO, CD86, DLK1, GNPAT, HSP90B1, LIPE
caveola 2 LIPE, PTGS2
extracellular exosome 6 CD86, F2, HSP90B1, KNG1, MBP, PDIA3
Lumenal side 1 HSD17B6
endoplasmic reticulum 5 AGMO, HSD17B6, HSP90B1, PDIA3, PTGS2
extracellular space 5 DLK1, F2, KNG1, LPL, PDIA3
perinuclear region of cytoplasm 1 HSP90B1
protein-containing complex 3 HSP90B1, MBP, PTGS2
intracellular membrane-bounded organelle 1 HSD17B6
Microsome membrane 2 HSD17B6, PTGS2
Single-pass type I membrane protein 1 CD86
Secreted 2 F2, LPL
extracellular region 5 F2, HSP90B1, KNG1, LPL, MBP
Single-pass membrane protein 2 DLK1, FAR1
Extracellular side 1 LPL
centriolar satellite 2 CD86, PRKCQ
external side of plasma membrane 1 CD86
Secreted, extracellular space, extracellular matrix 1 LPL
chylomicron 1 LPL
very-low-density lipoprotein particle 1 LPL
midbody 1 HSP90B1
Single-pass type II membrane protein 1 A4GALT
Matrix side 1 GNPAT
focal adhesion 2 HSP90B1, PDIA3
Peroxisome 2 FAR1, GNPAT
peroxisomal matrix 1 GNPAT
peroxisomal membrane 2 FAR1, GNPAT
collagen-containing extracellular matrix 4 F2, HSP90B1, KNG1, MBP
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 1 GABPA
cell periphery 1 MBP
[Isoform 3]: Nucleus 1 MBP
Secreted, extracellular space 1 KNG1
blood microparticle 2 F2, KNG1
Recycling endosome membrane 1 PDIA3
Endomembrane system 2 AGMO, GNPAT
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Melanosome 2 HSP90B1, PDIA3
myelin sheath 1 MBP
sperm plasma membrane 1 HSP90B1
Peroxisome membrane 2 FAR1, GNPAT
ficolin-1-rich granule lumen 1 MBP
Golgi lumen 1 F2
endoplasmic reticulum lumen 5 F2, HSP90B1, KNG1, PDIA3, PTGS2
platelet alpha granule lumen 1 KNG1
transport vesicle 1 MBP
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
Sarcoplasmic reticulum lumen 1 HSP90B1
MHC class I peptide loading complex 1 PDIA3
Tapasin-ERp57 complex 1 PDIA3
endocytic vesicle lumen 1 HSP90B1
compact myelin 1 MBP
internode region of axon 1 MBP
catalytic complex 1 LPL
endoplasmic reticulum chaperone complex 1 HSP90B1
[Bone marrow proteoglycan]: Secreted 1 MBP
Myelin membrane 1 MBP


文献列表

  • José Carlos Bozelli, Daniel Lu, G Ekin Atilla-Gokcumen, Richard M Epand. Promotion of plasmalogen biosynthesis reverse lipid changes in a Barth Syndrome cell model. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2020 06; 1865(6):158677. doi: 10.1016/j.bbalip.2020.158677. [PMID: 32126285]
  • Carolina Rodrigues Felix, Rashmi Gupta, Sandra Geden, Jill Roberts, Priscilla Winder, Shirley A Pomponi, Maria Cristina Diaz, John K Reed, Amy E Wright, Kyle H Rohde. Selective Killing of Dormant Mycobacterium tuberculosis by Marine Natural Products. Antimicrobial agents and chemotherapy. 2017 08; 61(8):. doi: 10.1128/aac.00743-17. [PMID: 28607021]
  • Jonas Bergan, Tore Skotland, Anne Berit Dyve Lingelem, Roger Simm, Bjørn Spilsberg, Toril Lindbäck, Tuulia Sylvänne, Helena Simolin, Kim Ekroos, Kirsten Sandvig. The ether lipid precursor hexadecylglycerol protects against Shiga toxins. Cellular and molecular life sciences : CMLS. 2014 Nov; 71(21):4285-300. doi: 10.1007/s00018-014-1624-1. [PMID: 24740796]
  • Pedro Brites, Ana Sofia Ferreira, Tiago Ferreira da Silva, Vera F Sousa, Ana R Malheiro, Marinus Duran, Hans R Waterham, Myriam Baes, Ronald J A Wanders. Alkyl-glycerol rescues plasmalogen levels and pathology of ether-phospholipid deficient mice. PloS one. 2011; 6(12):e28539. doi: 10.1371/journal.pone.0028539. [PMID: 22163031]
  • Anne-Laure Deniau, Paul Mosset, Frédérique Pédrono, Romain Mitre, Damien Le Bot, Alain B Legrand. Multiple beneficial health effects of natural alkylglycerols from shark liver oil. Marine drugs. 2010 Jul; 8(7):2175-84. doi: 10.3390/md8072175. [PMID: 20714431]
  • Masanori Honsho, Shunsuke Asaoku, Yukio Fujiki. Posttranslational regulation of fatty acyl-CoA reductase 1, Far1, controls ether glycerophospholipid synthesis. The Journal of biological chemistry. 2010 Mar; 285(12):8537-42. doi: 10.1074/jbc.m109.083311. [PMID: 20071337]
  • Hongying Zheng, Richard I Duclos, Conor C Smith, Harrison W Farber, Raphael A Zoeller. Synthesis and biological properties of the fluorescent ether lipid precursor 1-O-[9'-(1''-pyrenyl)]nonyl-sn-glycerol. Journal of lipid research. 2006 Mar; 47(3):633-42. doi: 10.1194/jlr.m500493-jlr200. [PMID: 16369049]
  • S Reynolds, H Cederberg, S Chakrabarty. Inhibitory effect of 1-O (2 methoxy) hexadecyl glycerol and phenylbutyrate on the malignant properties of human prostate cancer cells. Clinical & experimental metastasis. 2000; 18(4):309-12. doi: 10.1023/a:1011071907047. [PMID: 11448061]
  • K J Clark, A W Murray. Evidence that the bradykinin-induced activation of phospholipase D and of the mitogen-activated protein kinase cascade involve different protein kinase C isoforms. The Journal of biological chemistry. 1995 Mar; 270(13):7097-103. doi: 10.1074/jbc.270.13.7097. [PMID: 7535766]
  • B Rüstow, I Kolleck, F Guthmann, R Haupt, D Kunze, P Stevens. Synthesis and secretion of plasmalogens by type-II pneumocytes. The Biochemical journal. 1994 Sep; 302 ( Pt 3)(?):665-8. doi: 10.1042/bj3020665. [PMID: 7945189]
  • N Maulik, A Tosaki, R M Engelman, G A Cordis, D K Das. Myocardial salvage by 1-O-hexadecyl-Sn-glycerol: possible role of peroxisomal dysfunction in ischemia reperfusion injury. Journal of cardiovascular pharmacology. 1994 Sep; 24(3):486-92. doi: 10.1097/00005344-199409000-00018. [PMID: 7799644]
  • G Schulthess, G Lipka, S Compassi, D Boffelli, F E Weber, F Paltauf, H Hauser. Absorption of monoacylglycerols by small intestinal brush border membrane. Biochemistry. 1994 Apr; 33(15):4500-8. doi: 10.1021/bi00181a009. [PMID: 8161504]
  • J Palmblad, J Samuelsson, J Brohult. Interactions between alkylglycerols and human neutrophil granulocytes. Scandinavian journal of clinical and laboratory investigation. 1990 Jun; 50(4):363-70. doi: 10.3109/00365519009091592. [PMID: 2168089]
  • T Ishibashi, Y Imai. Affinity purification of alkylglycerol monooxygenase from rat liver microsomes by chimyl alcohol-Sepharose 4B column chromatography. Journal of lipid research. 1985 Mar; 26(3):393-5. doi: . [PMID: 3989395]
  • S Umeki, Y Nozawa. Thermoadaptive regulation of microsomal desaturase and electron-transport enzyme activities in lipid-manipulated Tetrahymena cells. Extent of unsaturated fatty acid production is dependent on membrane fluidity before temperature down-shift. Biochimica et biophysica acta. 1984 Mar; 793(1):123-8. doi: . [PMID: 6422990]
  • M C Cabot, C J Welsh, F Snyder. Increasing the levels of ether-linked lipids in L-M cells by glyceryl ether supplementation depresses growth and choline utilization. Biochimica et biophysica acta. 1982 Oct; 713(1):16-22. doi: 10.1016/0005-2760(82)90161-8. [PMID: 7138895]
  • C Gabrielides, V M Kapoulas. Metabolism of alpha-glyceryl ethers by Crithidia fasciculata. I. Study of the in vivo degradation of exogenous chimyl and batyl alcohols. The Journal of protozoology. 1981 Nov; 28(4):441-7. doi: 10.1111/j.1550-7408.1981.tb05317.x. [PMID: 7320947]