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Record Information
Version	2.0
Creation Date	2012-05-31 14:29:27 -0600
Update Date	2015-06-03 17:19:23 -0600
Secondary Accession Numbers	ECMDB20137
Identification
Name:	D-Erythro-3-Methylmalate
Description	D-erythro-3-methylmalate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6415720> Close
Synonyms:	(2R,3S)-2-hydroxy-3-methylbutanedioate (2R,3S)-2-hydroxy-3-methylbutanedioic acid (2R,3S)-3-methylmalate (2R,3S)-3-methylmalic acid D-Erythro-3-methylmalate D-Erythro-3-methylmalic acid
Chemical Formula:	C5H8O5
Weight:	Average: 148.114 Monoisotopic: 148.037173366
InChI Key:	NPYQJIHHTGFBLN-STHAYSLISA-N
InChI:	InChI=1S/C5H8O5/c1-2(4(7)8)3(6)5(9)10/h2-3,6H,1H3,(H,7,8)(H,9,10)/t2-,3+/m0/s1
CAS number:	Not Available
IUPAC Name:	(2R,3S)-2-hydroxy-3-methylbutanedioic acid
Traditional IUPAC Name:	D-erythro-3-methylmalate
SMILES:	[H][C@@](C)(C(O)=O)[C@@]([H])(O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Hydroxy fatty acids
Alternative Parents	Short-chain hydroxy acids and derivatives Methyl-branched fatty acids Beta hydroxy acids and derivatives Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Beta-hydroxy acid Branched fatty acid Hydroxy fatty acid Short-chain hydroxy acid Methyl-branched fatty acid Alpha-hydroxy acid Hydroxy acid Dicarboxylic acid or derivatives Secondary alcohol Carboxylic acid Carboxylic acid derivative Organooxygen compound Carbonyl group Alcohol Hydrocarbon derivative Organic oxide Organic oxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	erythro-3-methylmalic acid (CHEBI:27394 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 154 g/L ALOGPS logP -0.33 ALOGPS logP -0.57 ChemAxon logS 0.02 ALOGPS pKa (Strongest Acidic) 3.39 ChemAxon pKa (Strongest Basic) -4 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 94.83 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 29.45 m³·mol⁻¹ ChemAxon Polarizability 12.74 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Ketobutyric acid + Carbon dioxide + NADH + Hydrogen ion <> D-Erythro-3-Methylmalate + NAD Citraconic acid + Water <> D-Erythro-3-Methylmalate
SMPDB Pathways:	Not Available
KEGG Pathways:	C5-Branched dibasic acid metabolism ec00660 Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0f8a-3900000000-0757759d8479c38634f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a6r-9200000000-aafee9f80ad3d78f7d1e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a6r-9000000000-87d1de119df5d3bfdb12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f6t-2900000000-204aa7e58ea1ab8f7640 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0pi9-9500000000-0dca374ca1bbb677091b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-b2f353c995a6f56458b1 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 27394 HMDB ID Not Available Pubchem Compound ID 440892 Kegg ID C06032 ChemSpider ID 389722 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes