Oleamide (BioDeep_00000408474)
Main id: BioDeep_00000002283
natural product PANOMIX_OTCML-2023
代谢物信息卡片
9Z-octadecenamide
化学式: C18H35NO (281.2719)
中文名称: 油酸酰胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(CCCCCCC(=O)N)/C=C\CCCCCCCC
InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
描述信息
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives
D000074385 - Food Ingredients > D005503 - Food Additives
A fatty amide derived from oleic acid.
Oleamide is an endogenous fatty acid amide which can be synthesized de novo in the mammalian nervous system, and has been detected in human plasma.
同义名列表
5 个代谢物同义名
Oleamide; 9Z-octadecenamide; Oleic acid amide; Oleamide; Oleamide
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:116314
- KEGG: C19670
- PubChem: 5283387
- ChEMBL: CHEMBL15927
- LipidMAPS: LMFA08010004
- CAS: 301-02-0
- MoNA: CCMSLIB00004684211
- MetaboLights: MTBLC116314
- PubChem: 135626138
- RefMet: Oleamide
- medchemexpress: HY-N2327
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)
6 个相关的物种来源信息
- 1202408 - Desmos cochinchinensis: 10.1080/10575639508043184
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 3847 - Glycine max: 10.1002/PMIC.201700366
- 183589 - Pseudo-nitzschia multistriata: 10.3390/MD18060313
- 5691 - Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
- 29760 - Vitis vinifera: 10.3389/FMICB.2017.00457
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
- Carolina Y Reyes-Soto, Mariana Villaseca-Flores, Enid A Ovalle-Noguez, Jade Nava-Osorio, Sonia Galván-Arzate, Edgar Rangel-López, Marisol Maya-López, Socorro Retana-Márquez, Isaac Túnez, Alexey A Tinkov, Tao Ke, Michael Aschner, Abel Santamaría. Oleamide Reduces Mitochondrial Dysfunction and Toxicity in Rat Cortical Slices Through the Combined Action of Cannabinoid Receptors Activation and Induction of Antioxidant Activity.
Neurotoxicity research.
2022 Dec; 40(6):2167-2178. doi:
10.1007/s12640-022-00575-7. [PMID: 36069981] - Prapakorn Wisitpongpun, Pachuen Potup, Kanchana Usuwanthim. Oleamide-Mediated Polarization of M1 Macrophages and IL-1β Production by Regulating NLRP3-Inflammasome Activation in Primary Human Monocyte-Derived Macrophages.
Frontiers in immunology.
2022; 13(?):856296. doi:
10.3389/fimmu.2022.856296. [PMID: 35514993] - Andrzej L Dawidowicz, Michal P Dybowski, Michal Rombel, Rafal Typek. Improving the sensitivity of estimating CBD and other xenobiotics in plasma samples: Oleamide-induced transient matrix effect.
Journal of pharmaceutical and biomedical analysis.
2021 Sep; 204(?):114265. doi:
10.1016/j.jpba.2021.114265. [PMID: 34298472] - Yasuyuki Kobayashi, Natsumi Watanabe, Tomoya Kitakaze, Keiichiro Sugimoto, Takeshi Izawa, Kenji Kai, Naoki Harada, Ryoichi Yamaji. Oleamide rescues tibialis anterior muscle atrophy of mice housed in small cages.
The British journal of nutrition.
2021 08; 126(4):481-491. doi:
10.1017/s0007114520004304. [PMID: 33143796] - Hui Li, Yan Wang, Shizhao Ma, Chaoqun Zhang, Hua Liu, Dianxing Sun. Clinical significance of small molecule metabolites in the blood of patients with different types of liver injury.
Scientific reports.
2021 06; 11(1):11642. doi:
10.1038/s41598-021-91164-9. [PMID: 34079030] - Ahmed Wahab Obeng, Yaw Duah Boakye, Theresa Appiah Agana, Georgina Isabella Djameh, Daniel Boamah, Francis Adu. Anti-trypanosomal and anthelminthic properties of ethanol and aqueous extracts of Tetrapleura tetraptera Taub.
Veterinary parasitology.
2021 Jun; 294(?):109449. doi:
10.1016/j.vetpar.2021.109449. [PMID: 33991727] - Avik Roy, Madhuchhanda Kundu, Sudipta Chakrabarti, Dhruv R Patel, Kalipada Pahan. Oleamide, a Sleep-Inducing Supplement, Upregulates Doublecortin in Hippocampal Progenitor Cells via PPARα.
Journal of Alzheimer's disease : JAD.
2021; 84(4):1747-1762. doi:
10.3233/jad-215124. [PMID: 34744082] - Unchaleeporn Ameamsri, Arunrat Chaveerach, Runglawan Sudmoon, Tawatchai Tanee, Steve Peigneur, Jan Tytgat. Oleamide in Ipomoea and Dillenia Species and Inflammatory Activity Investigated through Ion Channel Inhibition.
Current pharmaceutical biotechnology.
2021; 22(2):254-261. doi:
10.2174/1389201021666200607185250. [PMID: 32515307] - Abdirahman Elmi, Rosella Spina, Arnaud Risler, Stéphanie Philippot, Ali Mérito, Raphaël E Duval, Fatouma Mohamed Abdoul-Latif, Dominique Laurain-Mattar. Evaluation of Antioxidant and Antibacterial Activities, Cytotoxicity of Acacia seyal Del Bark Extracts and Isolated Compounds.
Molecules (Basel, Switzerland).
2020 May; 25(10):. doi:
10.3390/molecules25102392. [PMID: 32455580] - Tian Li, Zhi F Zhou, Ping Zhang, Kun Qian, Tian C Zhang. Enhancing nitrobenzene biodegradation in aquatic systems: Feasibility of using plain soil as an inoculant and effects of adding ascorbic acid and peptone.
Chemosphere.
2020 Jan; 239(?):124806. doi:
10.1016/j.chemosphere.2019.124806. [PMID: 31726521] - Marisol Maya-López, Leonardo C Rubio-López, Ivana V Rodríguez-Alvarez, Julián Orduño-Piceno, Yuliza Flores-Valdivia, Aline Colonnello, Edgar Rangel-López, Isaac Túnez, Oscar Prospéro-García, Abel Santamaría. A Cannabinoid Receptor-Mediated Mechanism Participates in the Neuroprotective Effects of Oleamide Against Excitotoxic Damage in Rat Brain Synaptosomes and Cortical Slices.
Neurotoxicity research.
2020 Jan; 37(1):126-135. doi:
10.1007/s12640-019-00083-1. [PMID: 31286434] - I Lacatusu, N Badea, D Udeanu, L Coc, A Pop, C Cioates Negut, C Tanase, R Stan, A Meghea. Improved anti-obesity effect of herbal active and endogenous lipids co-loaded lipid nanocarriers: Preparation, in vitro and in vivo evaluation.
Materials science & engineering. C, Materials for biological applications.
2019 Jun; 99(?):12-24. doi:
10.1016/j.msec.2019.01.071. [PMID: 30889655] - Jie Zhang, Sudeepa Bhattacharyya, Robert C Hickner, Alan R Light, Christopher J Lambert, Bruce K Gale, Oliver Fiehn, Sean H Adams. Skeletal muscle interstitial fluid metabolomics at rest and associated with an exercise bout: application in rats and humans.
American journal of physiology. Endocrinology and metabolism.
2019 01; 316(1):E43-E53. doi:
10.1152/ajpendo.00156.2018. [PMID: 30398905] - Kuljeet S Gugnani, Nguyen Vu, Alejandro N Rondón-Ortiz, Mark Böhlke, Timothy J Maher, Alejandro J Pino-Figueroa. Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells.
Toxicology and applied pharmacology.
2018 02; 340(?):67-76. doi:
10.1016/j.taap.2017.12.014. [PMID: 29288688] - Oluwakemi Josephine Awakan, Sylvia Omonirume Malomo, Abdullahi Adeyinka Adejare, Adedoyin Igunnu, Olubunmi Atolani, Abiodun Humphrey Adebayo, Bamidele Victor Owoyele. Anti-inflammatory and bronchodilatory constituents of leaf extracts of Anacardium occidentale L. in animal models.
Journal of integrative medicine.
2018 01; 16(1):62-70. doi:
10.1016/j.joim.2017.12.009. [PMID: 29397096] - Hui Li, Su-Fang Fan, Yan Wang, Shi-Gang Shen, Dian-Xing Sun. Rapid Detection of Small Molecule Metabolites in Serum of Hepatocellular Carcinoma Patients Using Ultrafast Liquid Chromatography-Ion Trap-Time of Flight Tandem Mass Spectrometry.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2017; 33(5):573-578. doi:
10.2116/analsci.33.573. [PMID: 28496060] - Li Sun, Yufang Lu, Herbert J Kronzucker, Weiming Shi. Quantification and enzyme targets of fatty acid amides from duckweed root exudates involved in the stimulation of denitrification.
Journal of plant physiology.
2016 Jul; 198(?):81-8. doi:
10.1016/j.jplph.2016.04.010. [PMID: 27152459] - Woong-Suk Yang, Sung Ryul Lee, Yong Joon Jeong, Dae Won Park, Young Mi Cho, Hae Mi Joo, Inhye Kim, Young-Bae Seu, Eun-Hwa Sohn, Se Chan Kang. Antiallergic Activity of Ethanol Extracts of Arctium lappa L. Undried Roots and Its Active Compound, Oleamide, in Regulating FcεRI-Mediated and MAPK Signaling in RBL-2H3 Cells.
Journal of agricultural and food chemistry.
2016 May; 64(18):3564-73. doi:
10.1021/acs.jafc.6b00425. [PMID: 27087645] - J A Kaplan, P Barthélémy, M W Grinstaff. Self-assembled nanofiber hydrogels for mechanoresponsive therapeutic anti-TNFα antibody delivery.
Chemical communications (Cambridge, England).
2016 Apr; 52(34):5860-3. doi:
10.1039/c6cc02221a. [PMID: 27049283] - Ziqing Hei, Ailan Zhang, Jing Wei, Xiaoliang Gan, Yanling Wang, Gangjian Luo, Xiaoyun Li. Lipopolysaccharide effects on the proliferation of NRK52E cells via alternations in gap-junction function.
The journal of trauma and acute care surgery.
2012 Jul; 73(1):67-72. doi:
10.1097/ta.0b013e318256a0fe. [PMID: 22743374] - Emma K Farrell, Yuden Chen, Muna Barazanji, Kristen A Jeffries, Felipe Cameroamortegui, David J Merkler. Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells.
Journal of lipid research.
2012 Feb; 53(2):247-56. doi:
10.1194/jlr.m018606. [PMID: 22095832] - Gayong Shim, Su-Eun Han, Yong-Hee Yu, Sangbin Lee, Han Young Lee, Kwangmeyung Kim, Ick Chan Kwon, Tae Gwan Park, Young Bong Kim, Yong Seok Choi, Chan-Wha Kim, Yu-Kyoung Oh. Trilysinoyl oleylamide-based cationic liposomes for systemic co-delivery of siRNA and an anticancer drug.
Journal of controlled release : official journal of the Controlled Release Society.
2011 Oct; 155(1):60-6. doi:
10.1016/j.jconrel.2010.10.017. [PMID: 20971142] - Ranjith Munigunti, Nicholas Nelson, Vanisree Mulabagal, Mahabir P Gupta, Reto Brun, Angela I Calderón. Identification of oleamide in Guatteria recurvisepala by LC/MS-based Plasmodium falciparum thioredoxin reductase ligand binding method.
Planta medica.
2011 Oct; 77(15):1749-53. doi:
10.1055/s-0030-1271080. [PMID: 21567357] - Enrico Adriano, Luisa Perasso, Isabella Panfoli, Silvia Ravera, Carlo Gandolfo, Gianluigi Mancardi, Alessandro Morelli, Maurizio Balestrino. A novel hypothesis about mechanisms affecting conduction velocity of central myelinated fibers.
Neurochemical research.
2011 Oct; 36(10):1732-9. doi:
10.1007/s11064-011-0488-0. [PMID: 21553257] - Bénédicte Desforges, Philippe Savarin, Ouissame Bounedjah, Stéphanie Delga, Loïc Hamon, Patrick A Curmi, David Pastré. Gap junctions favor normal rat kidney epithelial cell adaptation to chronic hypertonicity.
American journal of physiology. Cell physiology.
2011 Sep; 301(3):C705-16. doi:
10.1152/ajpcell.00128.2011. [PMID: 21677260] - Bing Liu, Qin Wang, Dong-dong Yuan, Xiao-ting Hong, Liang Tao. Berberine potentizes apoptosis induced by X-rays irradiation probably through modulation of gap junctions.
Chinese medical journal.
2011 Apr; 124(8):1221-8. doi:
. [PMID: 21543001] - Ming-Ching Cheng, Yaw-Bee Ker, Tung-Hsi Yu, Li-Yun Lin, Robert Y Peng, Chiung-Huei Peng. Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds.
Journal of agricultural and food chemistry.
2010 Feb; 58(3):1502-8. doi:
10.1021/jf903573g. [PMID: 20078072] - Renjie Zhang, Helmuth Möhwald, Dirk G Kurth. One-step formation of straight nanostripes from a mammal lipid-oleamide directly on highly oriented pyrolytic graphite.
Langmuir : the ACS journal of surfaces and colloids.
2009 Feb; 25(4):2290-3. doi:
10.1021/la8035506. [PMID: 19125608] - Gregory P Mueller, William J Driscoll. Biosynthesis of oleamide.
Vitamins and hormones.
2009; 81(?):55-78. doi:
10.1016/s0083-6729(09)81003-0. [PMID: 19647108] - Xiu Yan Wei, Jing Yu Yang, Ying Xu Dong, Chun Fu Wu. Anxiolytic-like effects of oleamide in group-housed and socially isolated mice.
Progress in neuro-psychopharmacology & biological psychiatry.
2007 Aug; 31(6):1189-95. doi:
10.1016/j.pnpbp.2007.04.008. [PMID: 17521793] - William J Driscoll, Shalini Chaturvedi, Gregory P Mueller. Oleamide synthesizing activity from rat kidney: identification as cytochrome c.
The Journal of biological chemistry.
2007 Aug; 282(31):22353-63. doi:
10.1074/jbc.m610070200. [PMID: 17496328] - Yusuke Ohba, Yukiko Kanao, Nobuyoshi Morita, Eri Fujii, Mai Hohrai, Mayuko Takatsuji, Hideki Hirose, Daisaku Miura, Akihiro Watari, Masuo Yutsudo, Hanjun Zhao, Norikazu Yabuta, Akihiko Ito, Yasuyuki Kita, Hiroshi Nojima. Oleamide derivatives suppress the spontaneous metastasis by inhibiting connexin 26.
International journal of cancer.
2007 Jul; 121(1):47-54. doi:
10.1002/ijc.22608. [PMID: 17290388] - Kelly K Nichols, Bryan M Ham, Jason J Nichols, Corrie Ziegler, Kari B Green-Church. Identification of fatty acids and fatty acid amides in human meibomian gland secretions.
Investigative ophthalmology & visual science.
2007 Jan; 48(1):34-9. doi:
10.1167/iovs.06-0753. [PMID: 17197513] - Ivan Tubert-Brohman, Orlando Acevedo, William L Jorgensen. Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations.
Journal of the American Chemical Society.
2006 Dec; 128(51):16904-13. doi:
10.1021/ja065863s. [PMID: 17177441] - Shalini Chaturvedi, William J Driscoll, Brenda M Elliot, Martha M Faraday, Neil E Grunberg, Gregory P Mueller. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide.
Prostaglandins & other lipid mediators.
2006 Dec; 81(3-4):136-49. doi:
10.1016/j.prostaglandins.2006.09.001. [PMID: 17085322] - H Paul Ehrlich, Bonnie Sun, Gregory C Saggers, Fatuma Kromath. Gap junction communications influence upon fibroblast synthesis of Type I collagen and fibronectin.
Journal of cellular biochemistry.
2006 Jul; 98(4):735-43. doi:
10.1002/jcb.20852. [PMID: 16475185] - David J Merkler, Geoffrey H Chew, Andrew J Gee, Kathleen A Merkler, Jean-Paul O Sorondo, Mitchell E Johnson. Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells.
Biochemistry.
2004 Oct; 43(39):12667-74. doi:
10.1021/bi049529p. [PMID: 15449956] - Akihiko Ito, Nobuyoshi Morita, Daisaku Miura, Yu-Ichiro Koma, Tatsuki R Kataoka, Hiroshi Yamasaki, Yukihiko Kitamura, Yasuyuki Kita, Hiroshi Nojima. A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells.
Carcinogenesis.
2004 Oct; 25(10):2015-22. doi:
10.1093/carcin/bgh208. [PMID: 15205356] - Dolores Martínez-González, Herlinda Bonilla-Jaime, Adriana Morales-Otal, Steven J Henriksen, Javier Velázquez-Moctezuma, Oscar Prospéro-García. Oleamide and anandamide effects on food intake and sexual behavior of rats.
Neuroscience letters.
2004 Jun; 364(1):1-6. doi:
10.1016/j.neulet.2004.03.080. [PMID: 15193744] - Antonios Dougalis, George Lees, C Robin Ganellin. The sleep lipid oleamide may represent an endogenous anticonvulsant: an in vitro comparative study in the 4-aminopyridine rat brain-slice model.
Neuropharmacology.
2004 Mar; 46(4):541-54. doi:
10.1016/j.neuropharm.2003.10.011. [PMID: 14975678] - George Lees, Antonios Dougalis. Differential effects of the sleep-inducing lipid oleamide and cannabinoids on the induction of long-term potentiation in the CA1 neurons of the rat hippocampus in vitro.
Brain research.
2004 Jan; 997(1):1-14. doi:
10.1016/j.brainres.2003.10.019. [PMID: 14715144] - Antonios Dougalis, George Lees, C Robin Ganellin. The sleep inducing brain lipid cis-oleamide (cOA) does not modulate serotonergic transmission in the CA1 pyramidal neurons of the hippocampus in vitro.
Neuropharmacology.
2004 Jan; 46(1):63-73. doi:
10.1016/s0028-3908(03)00297-1. [PMID: 14654098] - Chun-Fu Wu, Chun-Li Li, Hong-Rui Song, Hua-Feng Zhang, Jing-Yu Yang, Yu-Ling Wang. Selective effect of oleamide, an endogenous sleep-inducing lipid amide, on pentylenetetrazole-induced seizures in mice.
The Journal of pharmacy and pharmacology.
2003 Aug; 55(8):1159-62. doi:
10.1211/0022357021431. [PMID: 12956907] - Ho-Jin Heo, Young-June Park, Young-Min Suh, Soo-Jung Choi, Mi-Jeong Kim, Hong-Yon Cho, Yun-Jeong Chang, Bumshik Hong, Hye-Kyung Kim, Eunki Kim, Chang-Ju Kim, Byung-Gee Kim, Dong-Hoon Shin. Effects of oleamide on choline acetyltransferase and cognitive activities.
Bioscience, biotechnology, and biochemistry.
2003 Jun; 67(6):1284-91. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2003 Feb; 100(3):1375-80. doi:
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Biophysical journal.
2002 Dec; 83(6):3393-407. doi:
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British journal of pharmacology.
2002 Apr; 135(8):1977-87. doi:
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Oncogene.
2002 Mar; 21(13):1989-99. doi:
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Molecular pharmacology.
2001 Dec; 60(6):1349-55. doi:
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Biochemical pharmacology.
2001 Nov; 62(10):1363-9. doi:
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Neuroscience letters.
2001 Nov; 313(1-2):61-4. doi:
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Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2001 Nov; 25(5 Suppl):S36-9. doi:
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Experimental neurology.
2001 Nov; 172(1):235-43. doi:
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The Journal of pharmacology and experimental therapeutics.
2001 Oct; 299(1):332-42. doi:
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Journal of agricultural and food chemistry.
2001 May; 49(5):2142-5. doi:
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The Journal of biological chemistry.
2001 Apr; 276(17):14133-8. doi:
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Life sciences.
2001 Jan; 68(9):997-1004. doi:
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Anesthesiology.
2001 Jan; 94(1):120-8. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2000 May; 97(10):5044-9. doi:
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Neuroscience letters.
2000 Mar; 282(1-2):13-6. doi:
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The Journal of cell biology.
2000 Mar; 148(5):1063-74. doi:
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Journal of dairy science.
2000 Mar; 83(3):569-76. doi:
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