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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:29:06 UTC
HMDB IDHMDB0000509
Secondary Accession Numbers
  • HMDB00509
Metabolite Identification
Common NameSenecioic acid
DescriptionSenecioic acid, also known as 3-methylcrotonate, 3-methylcrotonic acid or 3,3-dimethylacrylic acid, 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 (however senecioic acid is unsaturated) and contain only one or more methyl group. However, branches other than methyl may be present. Senecioic acid is a methyl-branched fatty acid that has a but-2-enoic acid skeleton bearing a methyl substituent at position 3. Senecioic acid is an unsaturated fatty acid found in the pheromones of mealybug species, the Madeira cockroach and the Southern long-nosed bat. It also appears in the urine of patients with 3-Methylcrotonic aciduria caused by 3-hydroxy-3-methylglutaryl-CoA lyase deficiency (PMID: 6157502 ) and those with 3-Hydroxy-3-methylglutaric aciduria (PMID: 947633 ). The appearance of 3-methylcrotonic acid in urine indicates a blockage in the sixth step of leucine catabolism, which is the cleavage of 3-hydroxy-3-methylglutaryl-CoA to acetoacetic acid and acetyl-CoA.
Structure
Data?1582752136
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
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
3-Methylbut-2-enoateHMDB
3-Methylbut-2-enoic acidHMDB
b,b-Dimethyl acrylateHMDB
b,b-Dimethyl acrylic acidHMDB
beta,beta-Dimethyl acrylateHMDB
Β,β-dimethyl acrylateHMDB
Β,β-dimethyl acrylic acidHMDB
Senecioic acidChEBI
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
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
  • 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling Point195.00 to 197.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility10 mg/mLNot Available
LogP1.350 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility71.1 g/LALOGPS
logP10(0.79) g/LALOGPS
logP10(1.16) g/LChemAxon
logS10(-0.15) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.01131661259
DarkChem[M-H]-115.42331661259
AllCCS[M+H]+123.56332859911
AllCCS[M-H]-122.86932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Senecioic acidCC(C)=CC(O)=O1713.4Standard polar33892256
Senecioic acidCC(C)=CC(O)=O974.6Standard non polar33892256
Senecioic acidCC(C)=CC(O)=O930.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Senecioic acid,1TMS,isomer #1CC(C)=CC(=O)O[Si](C)(C)C1014.3Semi standard non polar33892256
Senecioic acid,1TBDMS,isomer #1CC(C)=CC(=O)O[Si](C)(C)C(C)(C)C1221.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Senecioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgl-9100000000-fad992c9622a048041c82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Senecioic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9200000000-47cf47043dcc621a0e702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Senecioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Senecioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Senecioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0a4j-9000000000-92ace8b7ab3c75386bf22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Senecioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-052b-9000000000-ade4eabc58077e6357c82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Senecioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0002-9000000000-b803e5f392f789d436dd2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 10V, Positive-QTOFsplash10-001i-9200000000-ec7954ac0255b8c3e03c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 20V, Positive-QTOFsplash10-052u-9000000000-b6913d6ebb6c47b8e5822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 40V, Positive-QTOFsplash10-052u-9000000000-fa9b01b0a4c8a64e570a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 10V, Negative-QTOFsplash10-052b-9000000000-ad48b46e78b860433bb02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 20V, Negative-QTOFsplash10-0a5a-9000000000-b83dceb1bd0f86a7a4912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 40V, Negative-QTOFsplash10-0a59-9000000000-6b1083439ff18a99308e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 10V, Negative-QTOFsplash10-0002-9000000000-5289cc75fe7aae11de792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 20V, Negative-QTOFsplash10-000t-9000000000-40f2a490f543e03222422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 40V, Negative-QTOFsplash10-014i-9000000000-52adce5593fe6ee79db32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 10V, Positive-QTOFsplash10-053r-9000000000-2154212e0fc35a7a1e812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 20V, Positive-QTOFsplash10-0a4l-9000000000-7dd92e64eddf70e010a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Senecioic acid 40V, Positive-QTOFsplash10-000f-9000000000-87790895b0e53b400be72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1035401
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 ]
  4. 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 ]

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