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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:47 UTC
Update Date2021-10-13 06:16:16 UTC
HMDB IDHMDB0031518
Secondary Accession Numbers
  • HMDB31518
Metabolite Identification
Common NameD-Malic acid
DescriptionD-Malic acid, also known as D-malate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. D-Malic acid exists in all living organisms, ranging from bacteria to humans. D-Malic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on D-Malic acid.
Structure
Data?1563862135
Synonyms
ValueSource
(+)-D-Malic acidChEBI
(R)-2-Hydroxybutanedioic acidChEBI
2-HYDROXY-succinIC ACIDChEBI
D-MalateKegg
(+)-D-MalateGenerator
(R)-2-HydroxybutanedioateGenerator
2-HYDROXY-succinateGenerator
(R)-MalateHMDB
(R)-Hydroxybutanedioic acidHMDB
D-(+)-Malic acidHMDB
D-Hydroxybutanedioic acidHMDB
Hydroxy-(R)-butanedioic acidHMDB
R-Malic acidHMDB
D-Malic acidChEBI
Chemical FormulaC4H6O5
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
IUPAC Name(2R)-2-hydroxybutanedioic acid
Traditional Name.+-.-malic acid
CAS Registry Number636-61-3
SMILES
O[C@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
InChI KeyBJEPYKJPYRNKOW-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 °CNot Available
Boiling Point306.00 to 307.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility364 mg/mL at 20 °CNot Available
LogP-1.26Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker120.67930932474
[M-H]-Not Available120.679http://allccs.zhulab.cn/database/detail?ID=AllCCS00001764
Predicted Molecular Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
logP10(-0.87) g/LALOGPS
logP10(-1.1) g/LChemAxon
logS10(0.21) g/LALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.01731661259
DarkChem[M-H]-121.64831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Malic acidO[C@H](CC(O)=O)C(O)=O2199.2Standard polar33892256
D-Malic acidO[C@H](CC(O)=O)C(O)=O1008.0Standard non polar33892256
D-Malic acidO[C@H](CC(O)=O)C(O)=O1328.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Malic acid,1TMS,isomer #1C[Si](C)(C)O[C@H](CC(=O)O)C(=O)O1317.5Semi standard non polar33892256
D-Malic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O1311.4Semi standard non polar33892256
D-Malic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)CC(=O)O1279.0Semi standard non polar33892256
D-Malic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O1404.0Semi standard non polar33892256
D-Malic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C1376.6Semi standard non polar33892256
D-Malic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C1382.5Semi standard non polar33892256
D-Malic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1498.5Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C(=O)O1572.3Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O1571.3Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC(=O)O1555.1Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1851.7Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1836.9Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1825.4Semi standard non polar33892256
D-Malic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2116.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized)splash10-0002-0930000000-53a536e3bc82b8e916122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized)splash10-00di-9610000000-883e07f52319a029b9f92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized)splash10-0002-0930000000-53a536e3bc82b8e916122018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized)splash10-00di-9610000000-883e07f52319a029b9f92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Malic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-add08efe51cfe6d9243c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Malic acid GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Malic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Malic acid LC-ESI-QTOF , negative-QTOFsplash10-0159-3900000000-b601107a03ca7060bc562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOFsplash10-01b9-7900000000-7e16d13cd13953520b722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOFsplash10-00di-9000000000-ed4a8a4776b51e62327c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOFsplash10-0006-9000000000-22c9ebc50090b4cd66712021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 10V, Positive-QTOFsplash10-014i-6900000000-3b7d14a7ed7bb42627e42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 20V, Positive-QTOFsplash10-01bj-9300000000-20f68e610aeba32d19472015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 40V, Positive-QTOFsplash10-00dl-9000000000-044292489a383c81ae1d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOFsplash10-00m0-8900000000-9da4062d3c439ed2f7eb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOFsplash10-00ri-9200000000-c4d019ab4961e5b1a1ae2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOFsplash10-05fu-9000000000-bc073c2d0e1a2f8a82e32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOFsplash10-00y0-9400000000-b346287170f4b47937d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOFsplash10-00du-9000000000-94fcc5032bed94eae77e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOFsplash10-052f-9000000000-43c40f8a7715a996c55b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 10V, Positive-QTOFsplash10-00ri-9400000000-a20ca040dba0bb25ae2b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 20V, Positive-QTOFsplash10-0095-9000000000-90064952bc6def150ecc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Malic acid 40V, Positive-QTOFsplash10-0006-9000000000-4dd1a07ea5d3aab2c6ea2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03499
Phenol Explorer Compound IDNot Available
FooDB IDFDB008115
KNApSAcK IDNot Available
Chemspider ID83793
KEGG Compound IDC00497
BioCyc IDCPD-660
BiGG IDNot Available
Wikipedia LinkMalic_acid
METLIN IDNot Available
PubChem Compound92824
PDB IDDMR
ChEBI ID30796
Food Biomarker OntologyNot Available
VMH IDMAL_D
MarkerDB IDNot Available
Good Scents IDrw1107901
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.