1.0 2016-09-30 22:38:10 UTC 2020-06-04 21:21:22 UTC BMDB0000892 BMDB00892 Valeric acid Pentanoic acid, also known as valerate or N-pentanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Pentanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pentanoic acid exists in all living species, ranging from bacteria to humans. Pentanoic acid is a potentially toxic compound. 1-Butanecarboxylic acid CH3-[CH2]3-COOH N-BuCOOH N-Pentanoate N-Pentanoic acid N-Valeric acid Pentanoate Pentanoic acid Pentoic acid Propylacetic acid Valerate Valerianic acid Valeriansaeure Valeric acid, normal 1-Butanecarboxylate N-Valerate Pentoate Propylacetate Valerianate Valerate, normal 1-Pentanoate 1-Pentanoic acid Butanecarboxylate Butanecarboxylic acid Kyselina valerova N-C4H9COOH Valeriansaure Valeric acid normal N-Pentanoic acid, ammonium salt N-Pentanoic acid, potassium salt N-Pentanoic acid, sodium salt N-Pentanoic acid, zinc salt N-Pentanoic acid, maganese (+2) salt N-Pentanoic acid, 11C-labeled Lithium pentanoate N-Pentanoic acid, 11C-labeled sodium salt Valeric acid C5H10O2 102.1317 102.068079564 pentanoic acid N-valeric acid 109-52-4 CCCCC(O)=O InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) NQPDZGIKBAWPEJ-UHFFFAOYSA-N belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Straight chain fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative 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 short-chain fatty acid straight-chain saturated fatty acid Liquid melting_point -34 °C water_solubility 24.0 mg/mL logp 1.39 HANSCH,C ET AL. (1995) logp 1.34 ALOGPS logs -0.40 ALOGPS logp 1.37 ChemAxon pka_strongest_acidic 5.01 ChemAxon iupac pentanoic acid ChemAxon average_mass 102.1317 ChemAxon mono_mass 102.068079564 ChemAxon smiles CCCCC(O)=O ChemAxon formula C5H10O2 ChemAxon inchi InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) ChemAxon inchikey NQPDZGIKBAWPEJ-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 26.47 ChemAxon polarizability 11.23 ChemAxon rotatable_bond_count 3 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::EiMs 936 Specdb::MsIr 943 Specdb::MsIr 944 Specdb::MsIr 945 Specdb::CMs 3051 Specdb::CMs 29331 Specdb::CMs 29455 Specdb::CMs 37827 Specdb::CMs 99627 Specdb::CMs 99628 Specdb::CMs 173914 Specdb::NmrTwoD 1528 Specdb::MsMs 1253 Specdb::MsMs 1254 Specdb::MsMs 1255 Specdb::MsMs 4786 Specdb::MsMs 4787 Specdb::MsMs 4788 Specdb::MsMs 4789 Specdb::MsMs 4790 Specdb::MsMs 4791 Specdb::MsMs 4792 Specdb::MsMs 179388 Specdb::MsMs 179389 Specdb::MsMs 179390 Specdb::MsMs 181716 Specdb::MsMs 181717 Specdb::MsMs 181718 Specdb::MsMs 438586 Specdb::MsMs 438587 Specdb::MsMs 438588 Specdb::MsMs 438589 Specdb::MsMs 438590 Specdb::MsMs 438633 Specdb::MsMs 2264479 Specdb::MsMs 2264480 Specdb::MsMs 2264481 Specdb::NmrOneD 1586 Specdb::NmrOneD 2132 Specdb::NmrOneD 2819 Specdb::NmrOneD 5045 Specdb::NmrOneD 5046 Specdb::NmrOneD 7882 Specdb::NmrOneD 7883 Specdb::NmrOneD 7884 Specdb::NmrOneD 7885 Specdb::NmrOneD 7886 Specdb::NmrOneD 7887 Specdb::NmrOneD 7888 Specdb::NmrOneD 7889 Specdb::NmrOneD 7890 Specdb::NmrOneD 7891 Specdb::NmrOneD 7892 Specdb::NmrOneD 7893 Specdb::NmrOneD 7894 Specdb::NmrOneD 7895 Specdb::NmrOneD 7896 Specdb::NmrOneD 7897 Specdb::NmrOneD 7898 Specdb::NmrOneD 7899 Specdb::NmrOneD 7900 Specdb::NmrOneD 7901 Bladder 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 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 Milk 6.50 +/- 3.19 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 9 +/- 2 uM 1% milk by NMR 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 4.9 +/- 0.3 uM 2% milk by NMR 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 5 +/- 1 uM 3.25% milk by NMR 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 6 +/- 3 uM Skim milk by NMR 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 1.8 +/- 0.1 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 4.0 +/- 0.2 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 4.18 +/- 0.03 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 4.91 +/- 0.13 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 6.47 +/- 2.84 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 0.1 (0 - 0.4) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 5.44 +/- 2.61 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 0.2 (0.1 - 0.5) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 0.3 (0.1 - 0.6) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 1.5 (0.7 - 2.7) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Neuron 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 2865.03 +/- 2943.19 uM 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. Ruminal Fluid 1500-5000 uM By NMR Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid 764-1768 uM By NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Ruminal Fluid Detected by NMR in mid-lactating primiparous Holstein cows. Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr 4. 24617926 Ruminal Fluid 2932 +/- 433 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). 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. Ruminal Fluid 4033 +/- 557 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). 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. Ruminal Fluid 3000 +/- 807 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). 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. Ruminal Fluid 3044 +/- 1092 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. 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. Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid 2030 uM By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid 2510 uM By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 2700 uM By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 1410 uM By NMR. Primiparous Holstein cows, no barley grains in diet. Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 1450 +/- 330 uM O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6. 18328751 Ruminal Fluid 2739 +/- 677 uM By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 FDB003230 7701 7991 C00803 17418 DB02406 C00001208 Valeric acid 110 Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose. Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns. Journal of Chemical Technology and Biotechnology (2006), 81(3), 275-281. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)