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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:14:38 UTC
HMDB IDHMDB0000509
Secondary Accession Numbers
  • HMDB00509
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
Data?1547234078
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
3,3-DimethylacrylateGenerator
SenecioateGenerator
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
3-Methyl-crotonateHMDB
3-Methyl-crotonic acidHMDB
3-Methylbut-2-enoateHMDB
3-Methylbut-2-enoic 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 KeyYYPNJNDODFVZLE-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
  • 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:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.25 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgl-9100000000-fad992c9622a048041c8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9200000000-47cf47043dcc621a0e70View in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9200000000-ec7954ac0255b8c3e03cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-b6913d6ebb6c47b8e582View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-9000000000-fa9b01b0a4c8a64e570aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-9000000000-ad48b46e78b860433bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5a-9000000000-b83dceb1bd0f86a7a491View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-6b1083439ff18a99308eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Not SpecifiedNot Specified3-hydroxy-3-methylglutaryl-CoA Lyase Deficiency details
Associated Disorders and Diseases
Disease References
3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
  1. Jakobs C, Bojasch M, Duran M, Ketting D, Wadman SK, Leupold D: 3-methyl-3-butenoic acid: an artefact in the urinary metabolic pattern of patients with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency. Clin Chim Acta. 1980 Sep 8;106(1):85-9. [PubMed:6157502 ]
Associated OMIM IDs
  • 246450 (3-Hydroxy-3-methylglutaryl-CoA lyase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000736
KNApSAcK IDC00010280
Chemspider ID10468
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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. [PubMed: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. [PubMed: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. [PubMed:1249684 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Senecioic acid → 3,4,5-trihydroxy-6-[(3-methylbut-2-enoyl)oxy]oxane-2-carboxylic aciddetails