1.0 2016-09-30 22:34:57 UTC 2020-06-04 20:13:58 UTC BMDB0000691 BMDB00691 Malonic acid Malonate, also known as H2MALO or HOOC-CH2-COOH, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Malonate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Malonate exists in all living species, ranging from bacteria to humans. In cattle, malonate is involved in the metabolic pathway called fatty acid biosynthesis pathway. Malonate has been found to be associated with several diseases known as combined malonic and methylmalonic aciduria, eosinophilic esophagitis, early preeclampsia, and colorectal cancer; also malonate has been linked to the inborn metabolic disorders including malonyl-coa decarboxylase deficiency. H2Malo HOOC-CH2-COOH Propanedioic acid Propanedioate Malonate alpha,Omega-dicarboxylic acid Carboxyacetic acid Dicarboxylate Dicarboxylic acid Dicarboxymethane Kyselina malonova Malonate dicarboxylic acid Metahnedicarboxylic acid Methanedicarbonic acid Methanedicarboxylic acid Propanedioic acid dithallium salt Propanediolic acid Thallium malonate Malonic acid, 2-(14)C-labeled Malonic acid, monocalcium salt Malonic acid, 1,3-(14)C2-labeled Malonic acid, diammonium salt Malonic acid, disodium salt Malonic acid, dithallium salt Malonic acid, dipotassium salt Malonic acid, disodium salt, 1-(14)C-labeled Malonic acid, monosodium salt Malonic acid, potassium salt Malonic acid, sodium salt Thallous malonate Dithallium malonate Monosodium malonate Malonic acid C3H4O4 104.0615 104.010958616 propanedioic acid malonic acid 141-82-2 OC(=O)CC(O)=O InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) OFOBLEOULBTSOW-UHFFFAOYSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Dicarboxylic acids and derivatives 1,3-dicarbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides 1,3-dicarbonyl compound Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Aliphatic acyclic compounds Dicarboxylic acids alpha,omega-dicarboxylic acid Solid melting_point 135 °C water_solubility 763.0 mg/mL logp -0.81 HANSCH,C ET AL. (1995) logp -0.60 ALOGPS logs 0.28 ALOGPS logp -0.33 ChemAxon pka_strongest_acidic 2.43 ChemAxon iupac propanedioic acid ChemAxon average_mass 104.0615 ChemAxon mono_mass 104.010958616 ChemAxon smiles OC(=O)CC(O)=O ChemAxon formula C3H4O4 ChemAxon inchi InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) ChemAxon inchikey OFOBLEOULBTSOW-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 18.99 ChemAxon polarizability 8.13 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 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 Fatty Acid Biosynthesis SMP0087257 Specdb::EiMs 1607 Specdb::MsIr 745 Specdb::MsIr 746 Specdb::MsIr 747 Specdb::NmrTwoD 1426 Specdb::CMs 609 Specdb::CMs 610 Specdb::CMs 611 Specdb::CMs 968 Specdb::CMs 1083 Specdb::CMs 3106 Specdb::CMs 27638 Specdb::CMs 27911 Specdb::CMs 29831 Specdb::CMs 30130 Specdb::CMs 30216 Specdb::CMs 30619 Specdb::CMs 30885 Specdb::CMs 31192 Specdb::CMs 31193 Specdb::CMs 31874 Specdb::CMs 31875 Specdb::CMs 37699 Specdb::CMs 175367 Specdb::CMs 1072460 Specdb::CMs 1072461 Specdb::CMs 1072463 Specdb::MsMs 958 Specdb::MsMs 959 Specdb::MsMs 960 Specdb::MsMs 4423 Specdb::MsMs 4424 Specdb::MsMs 4425 Specdb::MsMs 4426 Specdb::MsMs 4427 Specdb::MsMs 4428 Specdb::MsMs 4429 Specdb::MsMs 179514 Specdb::MsMs 179515 Specdb::MsMs 179516 Specdb::MsMs 181842 Specdb::MsMs 181843 Specdb::MsMs 181844 Specdb::MsMs 438070 Specdb::MsMs 438071 Specdb::MsMs 438072 Specdb::MsMs 438073 Specdb::MsMs 438074 Specdb::MsMs 440028 Specdb::MsMs 451869 Specdb::MsMs 2227316 Specdb::MsMs 2232031 Specdb::NmrOneD 1253 Specdb::NmrOneD 1480 Specdb::NmrOneD 3836 Specdb::NmrOneD 144890 Specdb::NmrOneD 144891 Specdb::NmrOneD 144892 Specdb::NmrOneD 144893 Specdb::NmrOneD 144894 Specdb::NmrOneD 144895 Specdb::NmrOneD 144896 Specdb::NmrOneD 144897 Specdb::NmrOneD 144898 Specdb::NmrOneD 144899 Specdb::NmrOneD 144900 Specdb::NmrOneD 144901 Specdb::NmrOneD 144902 Specdb::NmrOneD 144903 Specdb::NmrOneD 144904 Specdb::NmrOneD 144905 Specdb::NmrOneD 144906 Specdb::NmrOneD 144907 Specdb::NmrOneD 144908 Specdb::NmrOneD 144909 Specdb::NmrOneD 166514 Specdb::NmrOneD 166583 Blood Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Kidney 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 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 Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. 23497994 Milk 407 Milk samples from Swedish Red cows Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. 25087032 Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Urine Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 C04025 DB02175 FDB008117 844 30794 867 MALONATE C00001193 Malonic_acid 3237 Behr, Arno; Botulinski, Andreas; Carduck, Franz Josef; Schneider, Michael. Process for preparation of malonic acid. Ger. Offen. (1992), 4 pp. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. 25087032 Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. 23497994 Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. 27236769 BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme BMDBP01668 Solute carrier family 1 member 4 A5HSH2 SLC1A4 Enzyme BMDBP01748 Amino acid transporter A5HSH3 SLC1A5 Enzyme BMDBP02100 Amino acid transporter A6H774 SLC1A6 Enzyme BMDBP02101 Solute carrier family 1 member 2 A5HSH1 SLC1A2 Enzyme BMDBP02136 Excitatory amino acid transporter 3 Q95135 SLC1A1 Enzyme BMDBP02137 Neutral amino acid transporter A A2VDL4 SLC1A4 Enzyme BMDBP02138 Neutral amino acid transporter B(0) Q95JC7 SLC1A5 Enzyme BMDBP02139 Excitatory amino acid transporter 1 P46411 SLC1A3 Enzyme BMDBP02140 Amino acid transporter A5HSH0 SLC1A1 Enzyme BMDBP02141 Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 2 Q3SYV8 SLC13A2 Enzyme BMDBP02142 Amino acid transporter A7MB31 SLC1A1 Enzyme BMDBP02143 Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 3 A1A4I3 SLC13A3 Enzyme BMDBP02144 Amino acid transporter Q866Q9 SLC1A4 Enzyme