Record Information
Version2.0
Creation Date2012-05-31 14:22:58 -0600
Update Date2015-06-03 17:19:07 -0600
Secondary Accession Numbers
  • ECMDB20015
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
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
Weight:Average: 134.0874
Monoisotopic: 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
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy 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 FrameworkAliphatic 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:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-9100000000-add08efe51cfe6d9243cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0930000000-53a536e3bc82b8e91612View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9610000000-883e07f52319a029b9f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-02j9-7191000000-b78c78194b39deee0ca4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0159-3900000000-b601107a03ca7060bc56View in MoNA
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

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:
dmlA
Uniprot ID:
P76251
Molecular weight:
40315
Reactions
(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
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
Uniprot ID:
P0A830
Molecular weight:
45436
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368