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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:46 UTC
HMDB IDHMDB00509
Secondary Accession NumbersNone
Metabolite Identification
Common NameSenecioic acid
DescriptionSenecioic acid appears in the urine of patients with 3-Methylcrotonic aciduria, which is a disorder characterised by urine that contains increased amounts of 3-methylcrotonic acid (Senecioic acid). It is caused by defects in a biotin-dependent reaction that forms 3-methylglutaconic acid. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
3,3-Dimethylacrylic acidChEBI
3-Methyl-2-butenoic acidChEBI
3-Methylcrotonic acidChEBI
beta,beta-Dimethacrylic acidChEBI
beta,beta-Dimethylacrylic acidChEBI
beta-Methylcrotonic acidChEBI
SENECIC ACIDChEBI
Senecioic acidChEBI
3,3-DimethylacrylateGenerator
3-Methylbut-2-enoateGenerator
3-Methyl-2-butenoateGenerator
3-MethylcrotonateGenerator
b,b-DimethacrylateGenerator
b,b-Dimethacrylic acidGenerator
beta,beta-DimethacrylateGenerator
β,β-dimethacrylateGenerator
β,β-dimethacrylic acidGenerator
b,b-DimethylacrylateGenerator
b,b-Dimethylacrylic acidGenerator
beta,beta-DimethylacrylateGenerator
β,β-dimethylacrylateGenerator
β,β-dimethylacrylic acidGenerator
b-MethylcrotonateGenerator
b-Methylcrotonic acidGenerator
beta-MethylcrotonateGenerator
β-methylcrotonateGenerator
β-methylcrotonic acidGenerator
SENECateGenerator
SenecioateGenerator
3-Methyl-crotonateHMDB
3-Methyl-crotonic acidHMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name3-methylbut-2-enoic acid
Traditional Nameβ,β-dimethacrylate
CAS Registry Number541-47-9
SMILES
CC(C)=CC(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)
InChI KeyInChIKey=YYPNJNDODFVZLE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility71.1 mg/mLALOGPS
logP0.79ALOGPS
logP1.16ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.25 m3·mol-1ChemAxon
Polarizability10.25 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4j-9000000000-92ace8b7ab3c75386bf2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052b-9000000000-ade4eabc58077e6357c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9000000000-b803e5f392f789d436ddView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000736
KNApSAcK IDC00010280
Chemspider ID10468
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00509
Metagene LinkHMDB00509
METLIN ID5495
PubChem Compound10931
PDB IDNot Available
ChEBI ID37127
References
Synthesis ReferenceIordache, Florin; Badica, Sonia; Ionescu, Alina; Badea, Florin. Synthesis of b,b-dimethylacrylic acid and its methyl and ethyl esters. Revistade Chimie (Bucharest, Romania) (1979), 30(7), 629-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406. [947633 ]
  2. Duran M, Ketting D, Wadman SK, Jakobs C, Schutgens RB, Veder HA: Organic acid excretion in a patient with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency: facts and artefacts. Clin Chim Acta. 1978 Dec 1;90(2):187-93. [719902 ]
  3. Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [1249684 ]