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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:20:10 UTC
Update Date2022-03-07 02:51:21 UTC
HMDB IDHMDB0012157
Secondary Accession Numbers
  • HMDB12157
Metabolite Identification
Common Name3-Methyl-2-butenal
Description3-Methyl-2-butenal, also known as senecialdehyde or 3,3-dimethylacrolein, belongs to the class of organic compounds known as enals. These are alpha,beta-unsaturated aldehydes of the general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. 3-methyl-2-butenal has been detected, but not quantified, in several different foods, such as common oregano, beechnuts, oval-leaf huckleberries, tea leaf willows, and red rice. This could make 3-methyl-2-butenal a potential biomarker for the consumption of these foods. 3-Methyl-2-butenal is a derivative of acrolein that is an alpha, beta-unsaturated carbonyl metabolite. It can be formed endogenously during lipid peroxidation or after oxidative stress, and is considered to play an important role in human carcinogenesis. The endogenously formed acroleins are a constant source of DNA damage, can lead to mutation, and can also induce tumours in humans (PMID:8319634 ). 3-Methyl-2-butenal, which is an unsaturated aldehyde bearing substitution at the alkene terminus, is a poor inactivator of the enzymes protein tyrosine phosphatases (PTPs). The inactivation of PTPs can yield profound biological consequences arising from the disruption of cellular signalling pathways (PMID:17655273 ).
Structure
Data?1586464852
Synonyms
ValueSource
3,3-Dimethyl-acrylaldehydeChEBI
3,3-DimethylacroleinChEBI
3-MethylcrotonaldehydeChEBI
beta,beta-DimethylacroleinChEBI
beta-MethylcrotonaldehydeChEBI
PrenalChEBI
SenecialdehydeChEBI
SenecioaldehydeChEBI
b,b-DimethylacroleinGenerator
Β,β-dimethylacroleinGenerator
b-MethylcrotonaldehydeGenerator
Β-methylcrotonaldehydeGenerator
3-Methylbut-2-enalHMDB
beta,beta-Dimethylacrylic aldehydeHMDB
2-Methyl-2-buten-4-alHMDB
3,3-DimethylacrylaldehydeHMDB
3-Methyl-2-buten-1-alHMDB
3-Methyl-2-butenalHMDB
3-Methyl-2-butenaldehydeHMDB
β,β-Dimethylacrylic aldehydeHMDB
Chemical FormulaC5H8O
Average Molecular Weight84.1164
Monoisotopic Molecular Weight84.057514878
IUPAC Name3-methylbut-2-enal
Traditional Nameprenal
CAS Registry Number107-86-8
SMILES
CC(C)=CC=O
InChI Identifier
InChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3
InChI KeySEPQTYODOKLVSB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point134 °CNot Available
Water Solubility0The Good Scents Company Information System
LogP1.190 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility63.6 g/LALOGPS
logP0.97ALOGPS
logP1ChemAxon
logS-0.12ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.32 m³·mol⁻¹ChemAxon
Polarizability9.51 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]+116.00531661259
DarkChem[M-H]-111.29631661259
DeepCCS[M+H]+121.12430932474
DeepCCS[M-H]-118.64130932474
DeepCCS[M-2H]-154.70930932474
DeepCCS[M+Na]+129.25630932474
AllCCS[M+H]+120.332859911
AllCCS[M+H-H2O]+115.832859911
AllCCS[M+NH4]+124.532859911
AllCCS[M+Na]+125.732859911
AllCCS[M-H]-125.032859911
AllCCS[M+Na-2H]-129.632859911
AllCCS[M+HCOO]-134.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methyl-2-butenalCC(C)=CC=O1098.1Standard polar33892256
3-Methyl-2-butenalCC(C)=CC=O707.7Standard non polar33892256
3-Methyl-2-butenalCC(C)=CC=O762.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methyl-2-butenal EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b788221762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methyl-2-butenal EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b788221762018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-2-butenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9000000000-5092b9dfda47020345ed2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-2-butenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-003r-9000000000-259c3199037e112aa7ef2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 10V, Negative-QTOFsplash10-001i-9000000000-392e24493caefed8d41d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 20V, Negative-QTOFsplash10-001i-9000000000-2568b7ba82ce5430fe4b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 40V, Negative-QTOFsplash10-014i-9000000000-1cc850ae9a5dbeac5dc72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 10V, Negative-QTOFsplash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 20V, Negative-QTOFsplash10-001i-9000000000-6b3dd865845396e5b2172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 40V, Negative-QTOFsplash10-00kf-9000000000-9b4ce98aee0a57ea19142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 10V, Positive-QTOFsplash10-000i-9000000000-de8a6eec89362bfff45a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 20V, Positive-QTOFsplash10-00kr-9000000000-0865f5d08c1ce95bdd582015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 40V, Positive-QTOFsplash10-0gbc-9000000000-32ba84192db5d33a736c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 10V, Positive-QTOFsplash10-0006-9000000000-bb5ff4f4247f9b92d7b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 20V, Positive-QTOFsplash10-0006-9000000000-c6adf8b427f15f31188a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-2-butenal 40V, Positive-QTOFsplash10-0006-9000000000-44aeba383c0994cb63262021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008134
KNApSAcK IDC00052688
Chemspider ID54980
KEGG Compound IDC15604
BioCyc IDPRENAL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61020
PDB IDNot Available
ChEBI ID15825
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1037231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Eder E, Hoffman C, Sporer S, Scheckenbach S: Biomonitoring studies and susceptibility markers for acrolein congeners and allylic and benzyl compounds. Environ Health Perspect. 1993 Mar;99:245-7. [PubMed:8319634 ]
  2. Seiner DR, LaButti JN, Gates KS: Kinetics and mechanism of protein tyrosine phosphatase 1B inactivation by acrolein. Chem Res Toxicol. 2007 Sep;20(9):1315-20. Epub 2007 Jul 27. [PubMed:17655273 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
3-Methyl-2-butenal → Prenoldetails