1.0 2016-09-30 22:52:44 UTC 2020-06-04 21:30:17 UTC BMDB0002212 BMDB02212 Arachidic acid Arachidic acid, also known as eicosanoic acid or eicosanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Arachidic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Arachidic acid is a potentially toxic compound. Arachic acid Arachidinic acid Arachinsaeure C20:0 CH3-[CH2]18-COOH Eicosanoic acid N-Eicosanoic acid Arachate Arachidinate Eicosanoate N-Eicosanoate Arachidate Eicosoic acid Icosanoic acid Eicosoate Icosanoate Arachidic acid C 20 C20 fatty acid FA(20:0) Peanut acid n-Eicosanic acid C20H40O2 312.5304 312.302830524 icosanoic acid arachidic acid 506-30-9 CCCCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) VKOBVWXKNCXXDE-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-chain fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Aliphatic acyclic compounds Saturated fatty acids Straight chain fatty acids Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid Solid melting_point 75.4 °C logp 9.29 SANGSTER (1993) logp 8.53 ALOGPS logs -6.80 ALOGPS logp 8.03 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac icosanoic acid ChemAxon average_mass 312.5304 ChemAxon mono_mass 312.302830524 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C20H40O2 ChemAxon inchi InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) ChemAxon inchikey VKOBVWXKNCXXDE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 95.49 ChemAxon polarizability 42.91 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 810 Specdb::CMs 1971 Specdb::CMs 12519 Specdb::CMs 29794 Specdb::CMs 30575 Specdb::CMs 31402 Specdb::CMs 32066 Specdb::CMs 38320 Specdb::CMs 167854 Specdb::EiMs 577 Specdb::NmrTwoD 1804 Specdb::NmrOneD 1865 Specdb::NmrOneD 2414 Specdb::NmrOneD 3104 Specdb::NmrOneD 269518 Specdb::NmrOneD 269519 Specdb::NmrOneD 269520 Specdb::NmrOneD 269521 Specdb::NmrOneD 269522 Specdb::NmrOneD 269523 Specdb::NmrOneD 269524 Specdb::NmrOneD 269525 Specdb::NmrOneD 269526 Specdb::NmrOneD 269527 Specdb::NmrOneD 269528 Specdb::NmrOneD 269529 Specdb::NmrOneD 269530 Specdb::NmrOneD 269531 Specdb::NmrOneD 269532 Specdb::NmrOneD 269533 Specdb::NmrOneD 269534 Specdb::NmrOneD 269535 Specdb::NmrOneD 269536 Specdb::NmrOneD 269537 Specdb::MsMs 2034 Specdb::MsMs 2035 Specdb::MsMs 2036 Specdb::MsMs 19853 Specdb::MsMs 19854 Specdb::MsMs 19855 Specdb::MsMs 21356 Specdb::MsMs 21357 Specdb::MsMs 21358 Specdb::MsMs 21404 Specdb::MsMs 21405 Specdb::MsMs 21406 Specdb::MsMs 22907 Specdb::MsMs 22908 Specdb::MsMs 22909 Specdb::MsMs 439522 Specdb::MsMs 439523 Specdb::MsMs 439524 Specdb::MsMs 439525 Specdb::MsMs 449579 Specdb::MsMs 449580 Specdb::MsMs 2238123 Specdb::MsMs 2239428 Specdb::MsMs 2240148 Specdb::MsMs 2241581 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Whole milk Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk 1599.844 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 2239.782 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 3519.658 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 4799.533 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Oocyte Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries. McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70. 10793638 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 1.3 +/- 0.2 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. 10467 C06425 28822 10035 FDB002927 ARACHIDIC_ACID Arachidic_acid C00001209 48230 401 Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. 19038946 M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021