2.0 2012-05-31 13:00:42 -0600 2015-09-13 15:15:19 -0600 ECMDB00718 M2MDB000177 Isovaleric acid Isovaleric acid, is a natural short-chain fatty acid. It is clear colorless liquid that is sparingly soluble in water, but extremely soluble in most common organic solvents. 3-Methyl-N-butyrate 3-Methyl-N-butyric acid 3-Methylbutanoate 3-Methylbutanoic acid 3-Methylbutyrate 3-Methylbutyrate: isopropyl-acetate 3-Methylbutyrate: isopropyl-Acetic acid 3-Methylbutyric acid 3-Methylbutyric acid: isopropyl-Acetate 3-Methylbutyric acid: isopropyl-Acetic acid B-Methylbutyrate B-Methylbutyric acid Beta-Methylbutyrate Beta-Methylbutyric acid Delphinate Delphinic acid Isopentanoate Isopentanoic acid Isopropylacetate Isopropylacetic acid Isovalerate Isovalerianate Isovalerianic acid Isovaleric acid β-Methylbutyrate β-Methylbutyric acid C5H10O2 102.1317 102.068079564 3-methylbutanoic acid isovaleric acid 503-74-2 CC(C)CC(O)=O InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7) GWYFCOCPABKNJV-UHFFFAOYSA-N Liquid Outer membrane Inner membrane logp 1.26 ALOGPS logs -0.20 ALOGPS solubility 6.49e+01 g/l ALOGPS melting_point -29.3 oC logp 1.21 ChemAxon pka_strongest_acidic 5.01 ChemAxon iupac 3-methylbutanoic acid ChemAxon average_mass 102.1317 ChemAxon mono_mass 102.068079564 ChemAxon smiles CC(C)CC(O)=O ChemAxon formula C5H10O2 ChemAxon inchi InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7) ChemAxon inchikey GWYFCOCPABKNJV-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 26.42 ChemAxon polarizability 10.99 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Valine Biosynthesis The pathway of valine biosynthesis starts with pyruvic acid interacting with a hydrogen ion through a acetolactate synthase / acetohydroxybutanoate synthase or a acetohydroxybutanoate synthase / acetolactate synthase resulting in the release of carbon dioxide and (S)-2-acetolactate. The latter compound then interacts with a hydrogen ion through an NADPH driven acetohydroxy acid isomeroreductase resulting in the release of a NADP and an (R) 2,3-dihydroxy-3-methylvalerate. The latter compound is then dehydrated by a dihydroxy acid dehydratase resulting in the release of water and isovaleric acid. Isovaleric acid interacts with an L-glutamic acid through a Valine Transaminase resulting in a oxoglutaric acid and an L-valine. L-valine is then transported into the periplasmic space through a L-valine efflux transporter. PW000812 Metabolic Specdb::CMs 2388 Specdb::CMs 27738 Specdb::CMs 29456 Specdb::CMs 37718 Specdb::CMs 99597 Specdb::CMs 99598 Specdb::CMs 137437 Specdb::CMs 145171 Specdb::CMs 1072733 Specdb::EiMs 1599 Specdb::NmrOneD 1260 Specdb::NmrOneD 1497 Specdb::NmrOneD 3882 Specdb::NmrOneD 4153 Specdb::NmrOneD 5065 Specdb::NmrOneD 5066 Specdb::NmrOneD 145090 Specdb::NmrOneD 145091 Specdb::NmrOneD 145092 Specdb::NmrOneD 145093 Specdb::NmrOneD 145094 Specdb::NmrOneD 145095 Specdb::NmrOneD 145096 Specdb::NmrOneD 145097 Specdb::NmrOneD 145098 Specdb::NmrOneD 145099 Specdb::NmrOneD 145100 Specdb::NmrOneD 145101 Specdb::NmrOneD 145102 Specdb::NmrOneD 145103 Specdb::NmrOneD 145104 Specdb::NmrOneD 145105 Specdb::NmrOneD 145106 Specdb::NmrOneD 145107 Specdb::NmrOneD 145108 Specdb::MsMs 1005 Specdb::MsMs 1006 Specdb::MsMs 1007 Specdb::MsMs 4516 Specdb::MsMs 4517 Specdb::MsMs 4518 Specdb::MsMs 4519 Specdb::MsMs 4520 Specdb::MsMs 12983 Specdb::MsMs 12984 Specdb::MsMs 12985 Specdb::MsMs 19655 Specdb::MsMs 19656 Specdb::MsMs 19657 Specdb::MsMs 437954 Specdb::MsMs 437955 Specdb::MsMs 437956 Specdb::MsMs 2258254 Specdb::MsMs 2258312 Specdb::MsMs 2260248 Specdb::MsMs 2393371 Specdb::MsMs 2393372 Specdb::MsMs 2393373 Specdb::MsMs 2572220 Specdb::MsMs 2572221 Specdb::NmrTwoD 1443 HMDB00718 10001 C08262 IVA Isovaleric_acid Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8. 11849623 Hoffmann GF, von Kries R, Klose D, Lindner M, Schulze A, Muntau AC, Roschinger W, Liebl B, Mayatepek E, Roscher AA: Frequencies of inherited organic acidurias and disorders of mitochondrial fatty acid transport and oxidation in Germany. Eur J Pediatr. 2004 Feb;163(2):76-80. Epub 2004 Jan 9. 14714182 Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. 8925066 Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. 16699586 Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. 2646392 Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp. http://hmdb.ca/system/metabolites/msds/000/000/637/original/HMDB00718.pdf?1358462362 Dihydroxy-acid dehydratase P05791 ILVD_ECOLI ilvD http://ecmdb.ca/proteins/P05791.xml Branched-chain-amino-acid aminotransferase P0AB80 ILVE_ECOLI ilvE http://ecmdb.ca/proteins/P0AB80.xml Short-chain fatty acids transporter P76460 ATOE_ECOLI atoE http://ecmdb.ca/proteins/P76460.xml Isovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine PW_R002886 (R)-2,3-Dihydroxy-isovalerate > Water + Isovaleric acid PW_R002885