1.0 2016-09-30 22:20:16 UTC 2020-05-21 16:28:23 UTC BMDB0000156 BMDB00156 L-Malic acid (S)-Malic acid, also known as malate or L-apple acid, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (S)-Malic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (S)-Malic acid exists in all eukaryotes, ranging from yeast to humans. (-)-L-Malic acid (S)-(-)-Hydroxysuccinic acid L-2-Hydroxybutanedioic acid L-Apple acid Malate Malic acid S-2-Hydroxybutanedioic acid L-Malate (-)-L-Malate (S)-(-)-Hydroxysuccinate L-2-Hydroxybutanedioate S-2-Hydroxybutanedioate (-)-(S)-Malate (-)-(S)-Malic acid (-)-Hydroxysuccinate (-)-Hydroxysuccinic acid (-)-Malic acid (2S)-2-Hydroxybutanedioate (2S)-2-Hydroxybutanedioic acid (S)-Hydroxy-butanedioate (S)-Hydroxy-butanedioic acid (S)-Hydroxybutanedioate (S)-Hydroxybutanedioic acid (S)-Malic acid Apple acid L-(-)-Malic acid L-Hydroxybutanedioate L-Hydroxybutanedioic acid L-Hydroxysuccinate L-Hydroxysuccinic acid S-(-)-Malate S-(-)-Malic acid (S)-Malate L-Malic acid (2S)-2-Hydroxysuccinic acid (2S)-Malic acid (S)-2-Hydroxysuccinic acid 2-Hydroxybutanedioic acid 2-Hydroxyethane-1,2-dicarboxylic acid 2-Hydroxysuccinic acid Deoxytetraric acid Hydroxybutanedioic acid Hydroxysuccinic acid Monohydroxybutanedioic acid alpha-Hydroxysuccinic acid α-Hydroxysuccinic acid C4H6O5 134.0874 134.021523302 (2S)-2-hydroxybutanedioic acid (-)-malic acid 97-67-6 O[C@@H](CC(O)=O)C(O)=O InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1 BJEPYKJPYRNKOW-REOHCLBHSA-N belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Beta hydroxy acids and derivatives Beta hydroxy acids and derivatives Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives Organic oxides Secondary alcohols Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Short-chain hydroxy acid Aliphatic acyclic compounds malic acid Solid melting_point 107 °C logp -0.87 ALOGPS logs 0.21 ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 3.2 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (2S)-2-hydroxybutanedioic acid ChemAxon average_mass 134.0874 ChemAxon mono_mass 134.021523302 ChemAxon smiles O[C@@H](CC(O)=O)C(O)=O ChemAxon formula C4H6O5 ChemAxon inchi InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1 ChemAxon inchikey BJEPYKJPYRNKOW-REOHCLBHSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 24.88 ChemAxon polarizability 10.93 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 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 Citric Acid Cycle SMP0087163 Pyruvate Metabolism SMP0087231 Transfer of Acetyl Groups into Mitochondria SMP0087254 Warburg Effect SMP0087270 Specdb::EiMs 2008 Specdb::NmrOneD 1115 Specdb::NmrOneD 1173 Specdb::NmrOneD 4687 Specdb::NmrOneD 4715 Specdb::NmrOneD 4825 Specdb::NmrOneD 4826 Specdb::NmrOneD 166495 Specdb::NmrTwoD 972 Specdb::NmrTwoD 1174 Specdb::CMs 377 Specdb::CMs 378 Specdb::CMs 379 Specdb::CMs 2662 Specdb::CMs 30362 Specdb::CMs 30363 Specdb::CMs 30787 Specdb::CMs 32358 Specdb::CMs 37326 Specdb::CMs 152285 Specdb::CMs 1051705 Specdb::CMs 1051707 Specdb::CMs 1051708 Specdb::CMs 1051709 Specdb::CMs 1051710 Specdb::CMs 1051711 Specdb::CMs 1051713 Specdb::CMs 1051715 Specdb::CMs 1051717 Specdb::CMs 1051718 Specdb::CMs 1051720 Specdb::CMs 1051722 Specdb::CMs 1051724 Specdb::MsMs 239 Specdb::MsMs 240 Specdb::MsMs 241 Specdb::MsMs 3119 Specdb::MsMs 3120 Specdb::MsMs 3121 Specdb::MsMs 3122 Specdb::MsMs 3123 Specdb::MsMs 3124 Specdb::MsMs 3125 Specdb::MsMs 3126 Specdb::MsMs 178632 Specdb::MsMs 178633 Specdb::MsMs 178634 Specdb::MsMs 180951 Specdb::MsMs 180952 Specdb::MsMs 180953 Specdb::MsMs 438046 Specdb::MsMs 438047 Specdb::MsMs 438048 Specdb::MsMs 438049 Specdb::MsMs 438050 Specdb::MsMs 438782 Specdb::MsMs 440042 Specdb::MsMs 2254556 Specdb::MsIr 234 Specdb::MsIr 235 Specdb::MsIr 236 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 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 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 Raw milk, by GC-TOF/MS Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 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 Prostate Tissue 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 C00149 FDB012047 193317 222656 30797 MAL C00001192 Malic acid 34045 McKenzie, Alex.; Plenderleith, H. J.; Walker, Nellie. Optical activation of racemic acid by d-malic acid. Journal of the Chemical Society, Transactions (1923), 123 2875-80. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 BMDBP00620 Malate dehydrogenase, cytoplasmic Q3T145 MDH1 Enzyme BMDBP02566 Malic enzyme B8YB77 ME1 Enzyme BMDBP02846 Fumarate hydratase Q148D3 FH Enzyme