Showing Compound Card for 3-Methyl-2-butenal (CDB005001)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 18:59:06 UTC
Updated at2020-12-07 19:11:26 UTC
CannabisDB IDCDB005001
Secondary Accession NumbersNot Available
Cannabis Compound 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 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. 3-Methyl-2-butenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-butenal exists in all living organisms, ranging from bacteria to humans. 3-Methyl-2-butenal is a sweet, almond, and brown tasting compound. Outside of the human body, 3-Methyl-2-butenal has been detected, but not quantified in, several different foods, such as wild celeries, chinese cinnamons, persimmons, cereals and cereal products, and beans. This could make 3-methyl-2-butenal a potential biomarker for the consumption of these foods. An enal consisting of but-2-ene with a methyl substituent at position 3 and an oxo group at position 1. 3-Methyl-2-butenal is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight84.12
Monoisotopic Molecular Weight84.0575
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point134 °CNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-003r-9000000000-259c3199037e112aa7ef2015-03-01View Spectrum
GC-MS3-Methyl-2-butenal, non-derivatized, GC-MS Spectrumsplash10-0a5c-9000000000-1ec92de58f3b78822176Spectrum
GC-MS3-Methyl-2-butenal, non-derivatized, GC-MS Spectrumsplash10-0a5c-9000000000-1ec92de58f3b78822176Spectrum
Predicted GC-MS3-Methyl-2-butenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053u-9000000000-5092b9dfda47020345edSpectrum
Predicted GC-MS3-Methyl-2-butenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-de8a6eec89362bfff45a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-0865f5d08c1ce95bdd582015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9000000000-32ba84192db5d33a736c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-392e24493caefed8d41d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-2568b7ba82ce5430fe4b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-1cc850ae9a5dbeac5dc72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-bb5ff4f4247f9b92d7b42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-c6adf8b427f15f31188a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-44aeba383c0994cb63262021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-6b3dd865845396e5b2172021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9b4ce98aee0a57ea19142021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.54 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Carbonyl reductase [NADPH] 1CBR121q22.13P16152 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012157
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Carbonyl reductase [NADPH] 1
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