Showing metabocard for Methylsuccinic acid (BMDB0001844)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:05 UTC
Update Date2020-04-22 15:08:50 UTC
BMDB IDBMDB0001844
Secondary Accession Numbers
  • BMDB01844
Metabolite Identification
Common NameMethylsuccinic acid
DescriptionMethylsuccinic acid, also known as methylsuccinate or 2-methylbutanedioate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Methylsuccinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methylsuccinic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MethylsuccinateGenerator
2-Methylbutanedioic acidHMDB
Methylsuccinic acid, (+-)-isomerHMDB
(S)-2-Hydroxy-2-methylsuccinateHMDB
(S)-2-Hydroxy-2-methylsuccinic acidHMDB
(S)-CitramalateHMDB
(S)-Citramalic acidHMDB
2-MethylbutanedioateHMDB
2-MethylsuccinateHMDB
2-Methylsuccinic acidHMDB
Methyl succinateHMDB
Methyl succinic acidHMDB
MethylbutanedioateHMDB
Methylbutanedioic acidHMDB
MEZHMDB
PyrotartarateHMDB
Pyrotartaric acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
IUPAC Name2-methylbutanedioic acid
Traditional Namemethylsuccinic acid
CAS Registry Number498-21-5
SMILES
CC(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyWXUAQHNMJWJLTG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility516.5 mg/mLHuman Metabolome Project
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.13ALOGPS
logP0.14ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.11 m³·mol⁻¹ChemAxon
Polarizability11.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0910000000-b99795b0e5069d573c2dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0920000000-c96774045667ea1804dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-b99795b0e5069d573c2dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-9100000000-bb48993db83be2104b10View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00du-9320000000-5f34c9f97642781028e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-3900000000-4afd6f9cd1309a7a392bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9600000000-e212a368f465b41cc1faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0l0i-9200000000-c712b36382fde51f3ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-f709b1c905420a006038View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0019-9400000000-40a1055d8102e323a077View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9400000000-f709b1c905420a006038View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0019-9400000000-40a1055d8102e323a077View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-e50cb8068b9ea6aa88c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9100000000-86a85f9d829697c248ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-687b61805462d04b5dedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-5900000000-4fd3ea5da8eb91f1951dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-9500000000-ec3019482baef20b293dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-23ddfbfc967e6df1168eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0077-9000000000-1bd08b69cec7f9966cb2View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001844
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022704
KNApSAcK IDNot Available
Chemspider ID9922
KEGG Compound IDC08645
BioCyc IDDIETHYL-2R3R-2-METHYL-3-HYDROXYSUCCIN
BiGG IDNot Available
Wikipedia Link2-Methylsuccinic acid
METLIN ID6344
PubChem Compound10349
PDB IDNot Available
ChEBI ID91315
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available