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(E)-2-Methylglutaconic acid (FDB022936)

Record Information
Version1.0
Creation date2011-09-21 00:21:59 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022936
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(E)-2-Methylglutaconic acid
Description2-Methylglutaconic acid is found in the urine of patients with organic aciduria from 2-methylacetoacetyl-CoA thiolase (EC 2.3.1.9, acetyl-CoA C-acetyltransferase) deficiency (ACAT, OMIM 607809). Main clinical features of ACAT include important staturo-ponderal delay, frequent infectious rhinopharyngitis episodes and an acute metabolic acidosis (this metabolic decompensation being adequately halted by bicarbonate supplementation). (PMID: 8930414, 2925825) [HMDB]
CAS Number53358-21-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.75 g/LALOGPS
logP0.3ALOGPS
logP0.44ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.59 m³·mol⁻¹ChemAxon
Polarizability13.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8O4
IUPAC name(2E)-2-methylpent-2-enedioic acid
InChI IdentifierInChI=1S/C6H8O4/c1-4(6(9)10)2-3-5(7)8/h2H,3H2,1H3,(H,7,8)(H,9,10)/b4-2+
InChI KeyJKGHDBJDBRBRNA-DUXPYHPUSA-N
Isomeric SMILESC\C(=C/CC(O)=O)C(O)=O
Average Molecular Weight144.1253
Monoisotopic Molecular Weight144.042258744
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
  • Unsaturated 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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
Predicted GC-MS(E)-2-Methylglutaconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6w-9200000000-3c26a0f7a91d6acef0f0Spectrum
Predicted GC-MS(E)-2-Methylglutaconic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9320000000-06523487fcb76b7974f7Spectrum
Predicted GC-MS(E)-2-Methylglutaconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4900000000-a4f5b1870a7ab5d7d9d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-9300000000-8690078e13fde4da86e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-3c72687cfe5825fe86202016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-eeb6bed3f0b5c36c6f792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-9400000000-650d0aa40bf2dd38635f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-a82ead692dae806005262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9200000000-624b23b748d39e75d3c42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-ebe23e1d52795153d3602021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-1af77fc95f979fc3b3802021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9600000000-be26d3e872704242dd9b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ea-9000000000-035726473be11e09463d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-b8174f664b8393ce68d62021-09-23View Spectrum
NMRNot Available
ChemSpider ID4897953
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6368126
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02266
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
Enzymes
NameGene NameUniProt ID
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrialMCCC2Q9HCC0
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialMCCC1Q96RQ3
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference