1.0 2016-09-30 22:37:27 UTC 2020-06-04 19:32:21 UTC BMDB0000847 BMDB00847 Pelargonic acid Nonanoic acid, also known as pelargon or nonanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Nonanoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Nonanoic acid exists in all living species, ranging from bacteria to humans. Nonanoic acid is a potentially toxic compound. 1-Nonanoic acid 1-Octanecarboxylic acid CH3-[CH2]7-COOH N-Nonanoic acid Nonanoate Nonansaeure Nonoic acid Nonylic acid Pelargic acid Pelargon Pelargonsaeure Pergonic acid 1-Nonanoate 1-Octanecarboxylate N-Nonanoate Nonanoic acid Nonoate Nonylate Pelargate Pergonate Pelargonate Cirrasol 185a Emery 1202 Emery'S L-114 Emfac 1202 Hexacid C-9 N-Nonoate N-Nonoic acid N-Nonylate N-Nonylic acid N-Pelargonate N-Pelargonic acid Pelargonic acid, calcium salt Potassium nonanoate Pelargonic acid, cadmium salt Pelargonic acid, sodium salt Pelargonic acid, zinc salt Pelargonic acid, aluminum salt Pelargonic acid, potassium salt FA(9:0) Pelargonic acid C9H18O2 158.238 158.13067982 nonanoic acid nonanoic acid 112-05-0 CCCCCCCCC(O)=O InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) FBUKVWPVBMHYJY-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Medium-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 Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Aliphatic acyclic compounds Straight chain fatty acids Straight chain fatty acids medium-chain fatty acid straight-chain saturated fatty acid Liquid melting_point 12.3 °C water_solubility 0.284 mg/mL logp 3.42 SANGSTER (1993) logp 3.47 ALOGPS logs -2.75 ALOGPS logp 3.14 ChemAxon pka_strongest_acidic 5.23 ChemAxon iupac nonanoic acid ChemAxon average_mass 158.238 ChemAxon mono_mass 158.13067982 ChemAxon smiles CCCCCCCCC(O)=O ChemAxon formula C9H18O2 ChemAxon inchi InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) ChemAxon inchikey FBUKVWPVBMHYJY-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 44.88 ChemAxon polarizability 19.49 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1507 Specdb::EiMs 793 Specdb::MsMs 1193 Specdb::MsMs 1194 Specdb::MsMs 1195 Specdb::MsMs 4715 Specdb::MsMs 4716 Specdb::MsMs 4717 Specdb::MsMs 4718 Specdb::MsMs 4719 Specdb::MsMs 4720 Specdb::MsMs 4721 Specdb::MsMs 7523 Specdb::MsMs 7524 Specdb::MsMs 7525 Specdb::MsMs 14195 Specdb::MsMs 14196 Specdb::MsMs 14197 Specdb::MsMs 438325 Specdb::MsMs 438326 Specdb::MsMs 438327 Specdb::MsMs 438328 Specdb::MsMs 438329 Specdb::MsMs 438670 Specdb::MsMs 2226880 Specdb::MsMs 2227809 Specdb::MsMs 2229244 Specdb::NmrOneD 1565 Specdb::NmrOneD 2158 Specdb::NmrOneD 2845 Specdb::NmrOneD 5079 Specdb::NmrOneD 5080 Specdb::MsIr 905 Specdb::MsIr 906 Specdb::MsIr 907 Specdb::CMs 656 Specdb::CMs 1075 Specdb::CMs 3413 Specdb::CMs 29031 Specdb::CMs 29470 Specdb::CMs 30119 Specdb::CMs 30649 Specdb::CMs 31245 Specdb::CMs 31947 Specdb::CMs 37800 Specdb::CMs 137156 Specdb::CMs 144890 Specdb::CMs 1079462 Epidermis 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 Liver 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 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 Liver 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 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 Milk 0.251 +/- 0.001 uM Commercial skim milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.468 +/- 0.012 uM Commercial 1% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.568 +/- 0.014 uM Commercial 2% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.64 +/- 0.02 uM Commercial 3.25% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 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 Semen Identified in bull spermatozoa by GC-MS Menezes EB, Velho ALC, Santos F, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Uncovering sperm metabolome to discover biomarkers for bull fertility. BMC Genomics. 2019 Sep 18;20(1):714. doi: 10.1186/s12864-019-6074-6. 31533629 FDB003306 7866 C01601 8158 29019 CPD-8505 C00030829 Nonanoic_acid 5810 Yu, Zhongjiang; Wang, Jinglin; Shi, Zhiming. Industrial process for producing azelaic acid and nonanoic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp. 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