MG(16:0/0:0/0:0) (BioDeep_00000017808)

 

Secondary id: BioDeep_00000173985, BioDeep_00000408189, BioDeep_00001874132

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer

化学式: C19H38O4 (330.2769948)
中文名称: 1-棕榈酸单甘油酯, 甘油单棕榈酸酯, 棕榈酸单甘油酯, (S)-2,3-二羟丙基十六酸酯
谱图信息: 最多检出来源 Viridiplantae(plant) 15.62%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

MG(16:0/0:0/0:0). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/mg(16:0_0:0_0:0) (retrieved 2024-09-19) (BioDeep RN: BioDeep_00000017808). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(=O)OCC(CO)O
InChI: InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3

描述信息

MG(16:0/0:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups: 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1/3-isomers are not distinguished from each other and are termed alpha-monoacylglycerols, while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. MG(16:0/0:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position. MG(16:0/0:0/0:0) is a minor component of olive oil and other vegetable oil.
MG(16:0/0:0/0:0) belongs to the family of monoradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at one fatty acyl group is attached. Their general formula is [R1]OCC(CO[R2])O[R3]. MG(16:0/0:0/0:0) is made up of one hexadecanoyl(R1).
1-Monopalmitin, a bitter melon extract, inhibits the P-glycoprotein (P-gp) activity in intestinal Caco-2 cells[1].
1-Monopalmitin, a bitter melon extract, inhibits the P-glycoprotein (P-gp) activity in intestinal Caco-2 cells[1].

同义名列表

82 个代谢物同义名

Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer; 2,3-Dihydroxypropyl ester(.+/-.)-hexadecanoic acid; Hexadecanoic acid, 2,3-bishydroxy propyl ester; Hexadecanoic acid, 2,3-dihydroxypropyl ester; Hexadexanoic acid 2,3-dihydroxypropyl ester; (S)-2,3-Dihydroxypropyl N-hexadecanoic acid; Hexadecanoate, 2,3-dihydroxypropyl ester; [(2S)-2,3-dihydroxypropyl] hexadecanoate; 1,2,3-Propanetriol 1-hexandecanoyl ester; (S)-2,3-Dihydroxypropyl N-hexadecanoate; (+-)-2,3-Dihydroxypropyl hexadecanoate; (2S)-2,3-dihydroxypropyl hexadecanoate; Hexadecanoic acid alpha-monoglyceride; 2,3-Dihydroxypropyl hexadecanoic acid; Palmitic acid alpha -monoglyceride; 2,3-Dihydroxypropyl hexadecanoate; Palmitic acid alpha-monoglyceride; (1)-2,3-Dihydroxypropyl palmitate; (S)-2,3-Dihydroxypropyl palmitate; Hexadecanoic acid α-monoglyceride; Palmitoyl glycerol, (+,-)-isomer; 1-Monohexadecanoyl-rac-glycerol; 2,3-Dihydroxypropyl palmitate; Palmitate alpha-monoglyceride; Palmitic acid a-monoglyceride; (2S)-1-O-Hexadecanoylglycerol; Palmitic acid α-monoglyceride; 1-Glyceryl monohexadecanoate; Glycerol 1-hexadecanoic acid; Glycerol 1-monopalmitic acid; Glycerol 1-monohexadecanoate; (±)-1-O-hexadecanoylglycerol; 1-MONOPALMITOYL-rac-glycerol; sn-1-Palmitoylmonoglyceride; (C16-C22)Trialkyl glyceride; rac-1(3)-Palmitoyl glycerol; sn-1-Palmitoylmonoglycerol; 1-hexadecanoyl-sn-glycerol; (±)-1-hexadecanoylglycerol; 1-Monohexadecanoylglycerol; (2S)-1-O-Palmitoylglycerol; Palmitate a-monoglyceride; 1-O-Palmitoyl-DL-glycerol; 1-Glycerol hexadecanoates; Glycerol alpha -palmitate; Palmitate α-monoglyceride; 1-Palmitoyl-rac-glycerol; Glycerol 3-palmitic acid; Glycerol 1-monopalmitate; Glycerol 1-palmitic acid; Glycerol 1-hexadecanoate; 1-O-Hexadecanoylglycerol; rac-Glycerol 1-palmitate; 1-Glyceryl hexadecanoate; L-(-)-alpha-Monopalmitin; 1-Monopalmitoylglycerol; Palmitin, 1-mono- (8ci); rac-1-Palmitoylglycerol; 1-Hexadecanoylglycerol; Glyceryl monopalmitate; Glyceryl palmitic acid; 1-O-Palmitoylglycerol; Glycerol 1-palmitate; Glycerol 3-palmitate; alpha -Monopalmitin; 1-Palmitoylglycerol; (S)-1-Monopalmitin; Palmitoyl glycerol; Glycerol palmitate; alpha-Monopalmitin; Glyceryl palmitate; (±)-1-monopalmitin; DL-1-Monopalmitin; DL-alpha-Palmitin; MG (16:0/0:0/0:0); Palmitin, 1-mono; MG(16:0/0:0/0:0); 1-mono-Palmitin; a-Monopalmitin; Α-monopalmitin; 1-Monopalmitin; MONOPALMITIN



数据库引用编号

13 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

201 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(201)

PharmGKB(0)

52 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。



文献列表

  • Lulu Niu, Wenwen Li, Xin Chen, Xiaosan Su, Jingjing Dong, Quanyang Liao, Xuhong Zhou, Shaoqing Shi, Ruifen Sun. 1-Monopalmitin promotes lung cancer cells apoptosis through PI3K/Akt pathway in vitro. Environmental toxicology. 2023 Jul; ?(?):. doi: 10.1002/tox.23897. [PMID: 37466199]
  • Magdalena Rudzińska, Aleksandra Grudniewska, Anna Chojnacka, Witold Gładkowski, Gabriela Maciejewska, Anna Olejnik, Katarzyna Kowalska. Distigmasterol-Modified Acylglycerols as New Structured Lipids-Synthesis, Identification and Cytotoxicity. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226837. [PMID: 34833929]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • W J Wu, Q Wang, W Zhang, L Li. [Discrimination and clinical value of plasma metabolomic profiles in multidrug resistant epithelial ovarian cancer]. Zhonghua zhong liu za zhi [Chinese journal of oncology]. 2017 Dec; 39(12):896-902. doi: 10.3760/cma.j.issn.0253-3766.2017.12.004. [PMID: 29262505]
  • Ramazan Erenler, Koksal Pabuccu, Ayse Sahin Yaglioglu, Ibrahim Demirtas, Fatih Gul. Chemical constituents and antiproliferative effects of cultured Mougeotia nummuloides and Spirulina major against cancerous cell lines. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2016 Mar; 71(3-4):87-92. doi: 10.1515/znc-2016-0010. [PMID: 26985685]
  • Monika Laner, Bruno A C Horta, Philippe H Hünenberger. Effect of the cosolutes trehalose and methanol on the equilibrium and phase-transition properties of glycerol-monopalmitate lipid bilayers investigated using molecular dynamics simulations. European biophysics journal : EBJ. 2014 Nov; 43(10-11):517-44. doi: 10.1007/s00249-014-0982-9. [PMID: 25150983]
  • Sadiqa Firdous, Nida Hassan Ansari, Itrat Fatima, Abdul Malik, Nighat Afza, Lubna Iqbal, Mehreen Lateef. Ophiamides A-B, new potent urease inhibitory sphingolipids from Heliotropium ophioglossum. Archives of pharmacal research. 2012 Jul; 35(7):1133-7. doi: 10.1007/s12272-012-0702-x. [PMID: 22864734]
  • Ami Oguro, Susumu Imaoka. Lysophosphatidic acids are new substrates for the phosphatase domain of soluble epoxide hydrolase. Journal of lipid research. 2012 Mar; 53(3):505-512. doi: 10.1194/jlr.m022319. [PMID: 22217705]
  • Meenakshi Sharma, Rakesh Sehgal, Sukhbir Kaur. Evaluation of nephroprotective and immunomodulatory activities of antioxidants in combination with cisplatin against murine visceral leishmaniasis. PLoS neglected tropical diseases. 2012; 6(5):e1629. doi: 10.1371/journal.pntd.0001629. [PMID: 22563510]
  • Masao Shimizu, Junya Moriwaki, Daisuke Shiiba, Hidenori Nohara, Naoto Kudo, Yoshihisa Katsuragi. Elimination of glycidyl palmitate in diolein by treatment with activated bleaching earth. Journal of oleo science. 2012; 61(1):23-8. doi: 10.5650/jos.61.23. [PMID: 22188803]
  • Yongcheng Huang, Jonathan C Cohen, Helen H Hobbs. Expression and characterization of a PNPLA3 protein isoform (I148M) associated with nonalcoholic fatty liver disease. The Journal of biological chemistry. 2011 Oct; 286(43):37085-93. doi: 10.1074/jbc.m111.290114. [PMID: 21878620]
  • Guozhong Dong, Shimin Liu, Yongxia Wu, Chunlong Lei, Jun Zhou, Sen Zhang. Diet-induced bacterial immunogens in the gastrointestinal tract of dairy cows: impacts on immunity and metabolism. Acta veterinaria Scandinavica. 2011 Aug; 53(?):48. doi: 10.1186/1751-0147-53-48. [PMID: 21824438]
  • Lianzhen Yu, Jiye Aa, Jin Xu, Min Sun, Sixuan Qian, Liping Cheng, Shuping Yang, Ruihua Shi. Metabolomic phenotype of gastric cancer and precancerous stages based on gas chromatography time-of-flight mass spectrometry. Journal of gastroenterology and hepatology. 2011 Aug; 26(8):1290-7. doi: 10.1111/j.1440-1746.2011.06724.x. [PMID: 21443661]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Mercedes Miñones Conde, J M Trillo, Olga Conde, Jose Miñones. Monolayer and Brewster angle microscopy studies of poly(methyl methacrylate)-monopalmitin mixed systems at the air-water interface. The journal of physical chemistry. B. 2010 Mar; 114(8):2695-703. doi: 10.1021/jp907900g. [PMID: 20121203]
  • Kirsi I Pakkanen, Lars Duelund, Matti Vuento, John Hjort Ipsen. Phase coexistence in a triolein-phosphatidylcholine system. Implications for lysosomal membrane properties. Chemistry and physics of lipids. 2010 Feb; 163(2):218-27. doi: 10.1016/j.chemphyslip.2009.11.007. [PMID: 19962372]
  • Wendong Xu, Chenggen Zhu, Wei Cheng, Xiaona Fan, Xiaoguang Chen, Sen Yang, Ying Guo, Fei Ye, Jiangong Shi. Chemical Constituents of the Roots of Euphorbia micractina. Journal of natural products. 2009 Sep; 72(9):1620-6. doi: 10.1021/np900305j. [PMID: 19702283]
  • Simon Grill, Corinne Rusterholz, Rosanna Zanetti-Dällenbach, Sevgi Tercanli, Wolfgang Holzgreve, Sinuhe Hahn, Olav Lapaire. Potential markers of preeclampsia--a review. Reproductive biology and endocrinology : RB&E. 2009 Jul; 7(?):70. doi: 10.1186/1477-7827-7-70. [PMID: 19602262]
  • Yong-Hui Li, Yi-Fang Yang, Kun Li, Li-Li Jin, Nian-Yun Yang, De-Yun Kong. 5 alpha-reductase and aromatase inhibitory constituents from Brassica rapa L. pollen. Chemical & pharmaceutical bulletin. 2009 Apr; 57(4):401-4. doi: 10.1248/cpb.57.401. [PMID: 19336936]
  • J F Lock, P Taheri, S Bauer, H-G Holzhütter, M Malinowski, P Neuhaus, M Stockmann. Interpretation of non-invasive breath tests using (13)C-labeled substrates--a preliminary report with (13)C-methacetin. European journal of medical research. 2009; 14(?):547-50. doi: 10.1186/2047-783x-14-12-547. [PMID: 20149989]
  • Yuyi Shen, Robert L Powell, Marjorie L Longo. Influence of the dissolution rate on the collapse and shedding behavior of monostearin/monopalmitin-rich coated microbubbles. Langmuir : the ACS journal of surfaces and colloids. 2008 Sep; 24(18):10035-40. doi: 10.1021/la801668h. [PMID: 18717575]
  • Shao-Hua Wu, Yue-Mao Shen, You-Wei Chen, Li-Yuan Yang, Shao-Lan Li, Zhi-Ying Li. [Studies on chemical constituents from stem bark of Trewia nudiflora]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jul; 33(13):1566-8. doi: ". [PMID: 18837316]
  • Do Yup Lee, Oliver Fiehn. High quality metabolomic data for Chlamydomonas reinhardtii. Plant methods. 2008 Apr; 4(?):7. doi: 10.1186/1746-4811-4-7. [PMID: 18442406]
  • Jessica X Jia, Kishor M Wasan. Effects of monoglycerides on rhodamine 123 accumulation, estradiol 17 beta-D-glucuronide bidirectional transport and MRP2 protein expression within Caco-2 cells. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2008; 11(3):45-62. doi: 10.18433/j33s3z. [PMID: 18801307]
  • Atta-Ur-Rahman, Nighat Sultana, Durre Shahwar, Muhammed Iqbal Choudhary. Two new fatty esters from Rhazya stricta roots (Apocynanaceae). Natural product research. 2008; 22(15):1350-4. doi: 10.1080/14786410701712897. [PMID: 19023793]
  • Wen-jie Qin, Gang-li Wang, Rui-chao Lin. [Studies on chemical constituents of Heterosmilax yunnanensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Aug; 30(8):959-61. doi: ". [PMID: 18074845]
  • Tilakavati Karupaiah, Kalyana Sundram. Effects of stereospecific positioning of fatty acids in triacylglycerol structures in native and randomized fats: a review of their nutritional implications. Nutrition & metabolism. 2007 Jul; 4(?):16. doi: 10.1186/1743-7075-4-16. [PMID: 17625019]
  • Erica Hernández-Galicia, Fernando Calzada, Rubén Roman-Ramos, Francisco J Alarcón-Aguilar. Monoglycerides and fatty acids from Ibervillea sonorae root: isolation and hypoglycemic activity. Planta medica. 2007 Mar; 73(3):236-40. doi: 10.1055/s-2007-967117. [PMID: 17318782]
  • Nuria Prim, Lars Iversen, Pilar Diaz, Thomas Bjørnholm. Atomic force microscope studies on the interactions of Candida rugosa lipase and supported lipidic bilayers. Colloids and surfaces. B, Biointerfaces. 2006 Oct; 52(2):138-42. doi: 10.1016/j.colsurfb.2006.05.018. [PMID: 16829060]
  • Nguyen Hai Dang, XinFeng Zhang, MingShan Zheng, Kun Ho Son, Hyeun Wook Chang, Hyun Pyo Kim, KiHwan Bae, Sam Sik Kang. Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb. Archives of pharmacal research. 2005 Jan; 28(1):28-33. doi: 10.1007/bf02975131. [PMID: 15742804]
  • Tomoko Konishi, Hideo Satsu, Yasuo Hatsugai, Koichi Aizawa, Takahiro Inakuma, Shinji Nagata, Sho-Hei Sakuda, Hiromichi Nagasawa, Makoto Shimizu. Inhibitory effect of a bitter melon extract on the P-glycoprotein activity in intestinal Caco-2 cells. British journal of pharmacology. 2004 Oct; 143(3):379-87. doi: 10.1038/sj.bjp.0705804. [PMID: 15351776]
  • Dae Sik Jang, Muriel Cuendet, Harry H S Fong, John M Pezzuto, A Douglas Kinghorn. Constituents of Asparagus officinalis evaluated for inhibitory activity against cyclooxygenase-2. Journal of agricultural and food chemistry. 2004 Apr; 52(8):2218-22. doi: 10.1021/jf0305229. [PMID: 15080623]
  • Tomoko Konishi, Hideo Satsu, Yasuo Hatsugai, Koichi Aizawa, Takahiro Inakuma, Shinji Nagata, Sho-hei Sakuda, Hiromichi Nagasawa, Makoto Shimizu. A bitter melon extract inhibits the P-glycoprotein activity in intestinal Caco-2 cells: monoglyceride as an active compound. BioFactors (Oxford, England). 2004; 22(1-4):71-4. doi: 10.1002/biof.5520220113. [PMID: 15630255]
  • Ming-ying Shang, Shao-qing Cai, Wen-han Lin, Min-chuan Wang, Jong-hee Park. [Studies on chemical constituents from the seed of Trigonella foenum-graecum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Apr; 27(4):277-9. doi: ". [PMID: 12774372]
  • I Lee, B Kadenbach. Palmitate decreases proton pumping of liver-type cytochrome c oxidase. European journal of biochemistry. 2001 Dec; 268(24):6329-34. doi: 10.1046/j.0014-2956.2001.02602.x. [PMID: 11737187]
  • I Kanesaka, T Hiura, S Suzuki, K Shimizu. Infrared spectra of 1 -monopalmitin- or 1-monostearin-water systems in the gel phase. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2001 Jul; 57(8):1621-6. doi: 10.1016/s1386-1425(01)00389-4. [PMID: 11471714]
  • A W Tumaney, S Shekar, R Rajasekharan. Identification, purification, and characterization of monoacylglycerol acyltransferase from developing peanut cotyledons. The Journal of biological chemistry. 2001 Apr; 276(14):10847-52. doi: 10.1074/jbc.m100005200. [PMID: 11283027]
  • X S Chen, D H Chen, J Y Si, G Z Tu. Chemical constituents of Typhonium giganteum Engl. Journal of Asian natural products research. 2001; 3(4):277-83. doi: 10.1080/10286020108040367. [PMID: 11783581]
  • J M Brewer, J Alexander. The adjuvant activity of non-ionic surfactant vesicles (niosomes) on the BALB/c humoral response to bovine serum albumin. Immunology. 1992 Apr; 75(4):570-5. doi: NULL. [PMID: 1592432]
  • Z Chao, J Liu. [Chemical constituents of the pericarp of Trichosanthes rosthornii Harms]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1991 Feb; 16(2):97-9, 127. doi: ". [PMID: 1872972]
  • S R Siddhanti, M W King, S B Tove. Influence of dietary fat on factors in serum that regulate thyroid cell metabolism. The Journal of nutrition. 1990 Nov; 120(11):1297-304. doi: 10.1093/jn/120.11.1297. [PMID: 2172489]
  • S B Tove, M Sutherland-Smith. Toxicity of rac-1(3)-myristoyl glycerol to mice. The Journal of nutrition. 1988 Dec; 118(12):1463-9. doi: 10.1093/jn/118.12.1463. [PMID: 3210075]
  • P Trumbo, M Sutherland-Smith, B Kitchell, S B Tove. The result of feeding palmitoyl glycerol on lymph and plasma lipids. Lipids. 1987 Dec; 22(12):1009-15. doi: 10.1007/bf02536441. [PMID: 3451005]
  • N R Bachur, R L Felsted. Oxisuran reduction by rabbit tissue preparations. Drug metabolism and disposition: the biological fate of chemicals. 1976 May; 4(3):239-43. doi: NULL. [PMID: 6228]
  • . . . . doi: . [PMID: 20554061]