(R)-Malate (PAMDB000864)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000864
Identification
Name: (R)-Malate
Description:Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (+)-D-malate
  • (+)-D-malic acid
  • (+-)-1-Hydroxy-1,2-ethanedicarboxylate
  • (+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
  • (-)-1-Hydroxy-1,2-ethanedicarboxylate
  • (-)-1-Hydroxy-1,2-ethanedicarboxylic acid
  • (-)-hydroxysuccinate
  • (-)-hydroxysuccinic acid
  • (-)-L-malate
  • (-)-L-malic acid
  • (-)-malate
  • (-)-malic acid
  • (2R)-2-hydroxybutanedioate
  • (2R)-2-hydroxybutanedioic acid
  • (2S)-2-Hydroxybutanedioate
  • (2S)-2-Hydroxybutanedioic acid
  • (R)-(+)-2-Hydroxysuccinate
  • (R)-(+)-2-Hydroxysuccinic acid
  • (R)-hydroxybutanedioate
  • (R)-hydroxybutanedioic acid
  • (R)-malate
  • (R)-Malic acid
  • (S)-2-Hydroxybutanedioate
  • (S)-2-Hydroxybutanedioic acid
  • (S)-Hydroxybutanedioate
  • (S)-Hydroxybutanedioic acid
  • (S)-malate
  • (S)-malic acid
  • .+-.-malate
  • .+-.-malic acid
  • 2-Hydroxy-Butanedioate
  • 2-Hydroxy-Butanedioic acid
  • 2-HYDROXY-succinate
  • 2-HYDROXY-SUCCINIC ACID
  • 2-Hydroxybutanedioate
  • 2-Hydroxybutanedioic acid
  • 2-Hydroxydicarboxylate
  • 2-Hydroxydicarboxylic acid
  • 2-Hydroxyethane-1,2-dicarboxylate
  • 2-Hydroxyethane-1,2-dicarboxylic acid
  • 2-Hydroxysuccinate
  • 2-Hydroxysuccinic acid
  • A-Hydroxysuccinate
  • A-Hydroxysuccinic acid
  • Aepfelsaeure
  • Alpha-Hydroxysuccinate
  • Alpha-Hydroxysuccinic acid
  • Apple acid
  • Butanedioate, hydroxy-, (S)- (9CI)
  • Butanedioate, hydroxy-, homopolymer
  • Butanedioic acid, hydroxy-, (S)- (9CI)
  • Butanedioic acid, hydroxy-, homopolymer
  • D-(+)-Malate
  • D-(+)-Malic acid
  • D-Hydroxybutanedioate
  • D-Hydroxybutanedioic acid
  • D-Malate
  • D-Malic acid
  • Deoxytetrarate
  • Deoxytetraric acid
  • DL-hydroxybutanedioate
  • DL-hydroxybutanedioic acid
  • DL-Malate
  • DL-malic acid
  • DL-malic disodium salt
  • DMR
  • H2mal
  • Hydroxy-(.+-.)-Butanedioate
  • Hydroxy-(.+-.)-Butanedioic acid
  • Hydroxy-(.+/-.)-Butanedioate
  • Hydroxy-(.+/-.)-Butanedioic acid
  • Hydroxy-(2S)-Butanedioate
  • Hydroxy-(2S)-Butanedioic acid
  • Hydroxy-(R)-Butanedioate
  • Hydroxy-(R)-Butanedioic acid
  • Hydroxy-(S)-Butanedioate
  • Hydroxy-(S)-Butanedioic acid
  • Hydroxy-Butanedioate
  • Hydroxy-Butanedioic acid
  • Hydroxy-Succinate
  • Hydroxy-Succinic acid
  • Hydroxybutandisaeure
  • Hydroxybutanedioate
  • Hydroxybutanedioate homopolymer
  • Hydroxybutanedioic acid
  • Hydroxybutanedioic acid homopolymer
  • Hydroxysuccinate
  • Hydroxysuccinic acid
  • Hydroxysuccinnate (-)
  • Hydroxysuccinnic acid (-)
  • Kyselina hydroxybutandiova [czech]
  • Kyselina jablecna
  • Kyselina jablecna [czech]
  • L(+)-Malate
  • L(+)-Malic acid
  • L-(-)-Malate
  • L-(-)-Malic acid
  • L-Mal
  • L-Malate
  • L-Malic acid
  • MAL
  • Malate
  • Malate D-(+)-form
  • Malate homopolymer
  • Malate L-(-)-form
  • Malate,(DL)
  • Malic acid
  • Malic acid D-(+)-form
  • Malic acid homopolymer
  • Malic acid L-(-)-form
  • Malic acid,(DL)
  • MLT
  • Monohydroxybernsteinsaeure
  • Musashi-no-ringosan
  • Nchembio.145-comp29
  • OAA
  • Poly (L-malate)
  • Poly (L-malic acid)
  • Poly(malate)
  • Poly(malic acid)
  • Pomalus acid
  • R,S(+-)-Malate
  • R,S(+-)-Malic acid
  • R,S-Malate
  • R,S-Malic acid
  • R,Smalate
  • R,Smalic acid
  • R-Malate
  • R-Malic acid
  • S-(-)-Malate
  • S-(-)-Malic acid
  • S-2-Hydroxybutanedioate
  • S-2-Hydroxybutanedioic acid
  • TEO
  • α-Hydroxysuccinate
  • α-Hydroxysuccinic acid
Chemical Formula: C4H6O5
Average Molecular Weight: 134.0874
Monoisotopic Molecular Weight: 134.021523302
InChI Key: BJEPYKJPYRNKOW-UWTATZPHSA-N
InChI:InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
CAS number: 636-61-3
IUPAC Name:(2R)-2-hydroxybutanedioic acid
Traditional IUPAC Name: .+-.-malic acid
SMILES:O[C@H](CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 131-133 °C
Experimental Properties:
PropertyValueSource
Water Solubility:364 mg/mL at 20 oC [BEILSTEIN]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility218.0 mg/mLALOGPS
logP-0.87ALOGPS
logP-1.1ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m3·mol-1ChemAxon
Polarizability10.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
(R)-Malate + NAD <> Carbon dioxide + NADH + Pyruvic acid
(R)-Malate + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000000-3b7d14a7ed7bb42627e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bj-9300000000-20f68e610aeba32d1947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-044292489a383c81ae1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00m0-8900000000-9da4062d3c439ed2f7ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-9200000000-c4d019ab4961e5b1a1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-bc073c2d0e1a2f8a82e3View 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID30796
HMDB IDHMDB31518
Pubchem Compound ID92824
Kegg IDC00497
ChemSpider ID510
Wikipedia IDNot Available
BioCyc IDCPD-660
EcoCyc IDCPD-660
Ligand ExpoMLT

Enzymes

Transporters

Protein Details
• Aerobic C4-dicarboxylate transport protein
General function:
Involved in symporter activity
Specific function:
Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
Gene Name:
dctA
Locus Tag:
PA1183
Molecular weight:
46 kDa