Record Information
Version2.0
Creation Date2012-05-31 14:29:27 -0600
Update Date2015-06-03 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
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility154 g/LALOGPS
logP-0.33ALOGPS
logP-0.57ChemAxon
logS0.02ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.45 m³·mol⁻¹ChemAxon
Polarizability12.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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 TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2900000000-204aa7e58ea1ab8f7640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi9-9500000000-0dca374ca1bbb677091bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b2f353c995a6f56458b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-3900000000-0757759d8479c38634f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9200000000-aafee9f80ad3d78f7d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-87d1de119df5d3bfdb12View in MoNA
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
External Links:
ResourceLink
CHEBI ID27394
HMDB IDNot Available
Pubchem Compound ID440892
Kegg IDC06032
ChemSpider ID389722
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in 3-isopropylmalate dehydratase activity
Specific function:
Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:
leuC
Uniprot ID:
P0A6A6
Molecular weight:
49882
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the oxidation of 3-carboxy-2-hydroxy-4- methylpentanoate (3-isopropylmalate) to 3-carboxy-4-methyl-2- oxopentanoate. The product decarboxylates to 4-methyl-2 oxopentanoate
Gene Name:
leuB
Uniprot ID:
P30125
Molecular weight:
39517
Reactions
(2R,3S)-3-isopropylmalate + NAD(+) = 4-methyl-2-oxopentanoate + CO(2) + NADH.
General function:
Involved in 3-isopropylmalate dehydratase activity
Specific function:
Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:
leuD
Uniprot ID:
P30126
Molecular weight:
22487
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.