Record Information
Version1.0
Creation date2011-09-21 00:18:13 UTC
Update date2015-10-09 22:30:52 UTC
Primary IDFDB022704
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethylsuccinic acid
DescriptionMethylsuccinic acid is a normal metabolite found in human fluids. Increased urinary levels of Methylsuccinic acid (together with ethylmalonic acid) are the main biochemical measurable features in ethylmalonic encephalopathy (OMIM 602473 ), a rare metabolic disorder with an autosomal recessive mode of inheritance that is clinically characterized by neuromotor delay, hyperlactic acidemia, recurrent petechiae, orthostatic acrocyanosis, and chronic diarrhea. (PMID 12382164) T he underlying biochemical defect involves isoleucine catabolism. (PMID 9667231) It has been found decreases in the urine of animals under D-serine-induced nephrotoxicity (D-Serine causes selective necrosis of the proximal straight tubules in the rat kidney). (PMID 15596249) [HMDB]
CAS Number498-21-5
Structure
Thumb
Synonyms
SynonymSource
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
Methyl Succinic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility103 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O4
IUPAC name2-methylbutanedioic acid
InChI IdentifierInChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyWXUAQHNMJWJLTG-UHFFFAOYSA-N
Isomeric SMILESCC(CC(O)=O)C(O)=O
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0077-9000000000-1bd08b69cec7f9966cb22014-09-20View Spectrum
GC-MSMethylsuccinic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-b99795b0e5069d573c2dSpectrum
GC-MSMethylsuccinic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-c96774045667ea1804dfSpectrum
GC-MSMethylsuccinic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-b99795b0e5069d573c2dSpectrum
Predicted GC-MSMethylsuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007c-9100000000-bb48993db83be2104b10Spectrum
Predicted GC-MSMethylsuccinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00du-9320000000-5f34c9f97642781028e4Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-3900000000-4afd6f9cd1309a7a392b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9600000000-e212a368f465b41cc1fa2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0l0i-9200000000-c712b36382fde51f3ae52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-f709b1c905420a0060382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0019-9400000000-40a1055d8102e323a0772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9400000000-f709b1c905420a0060382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0019-9400000000-40a1055d8102e323a0772017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-e50cb8068b9ea6aa88c82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9100000000-86a85f9d829697c248dd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-687b61805462d04b5ded2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-5900000000-4fd3ea5da8eb91f1951d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-9500000000-ec3019482baef20b293d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-23ddfbfc967e6df1168e2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID9922
ChEMBL IDNot Available
KEGG Compound IDC08645
Pubchem Compound ID10349
Pubchem Substance IDNot Available
ChEBI ID29003
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01844
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference