Showing Compound Card for 2-Methyl butanoic acid (CDB005783)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-27 16:56:09 UTC
Updated at2021-01-04 18:49:17 UTC
CannabisDB IDCDB005783
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Methyl butanoic acid
DescriptionEthylmethylacetic acid, also known as alpha-methyl butyrate, 2-methylbutyric acid or 2-methylbutanoic 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 and contain only one or more methyl group. However, branches other than methyl may be present. 2-methylbutanoic acid (ethylmethylacetic acid) occurs in two enantiomeric forms, (R)-2-methylbutanoic and (S)-2-methylbutanoic acid. (R)-2-Methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots. The ethyl ester of 2-methylbutanoic acid is found in pineapples and oranges. 2-Methylbutanoic acid is a slightly volatile, colorless liquid with an unpleasant odor that is sparingly soluble in water. The smell differs significantly between the two forms. (S)-2-Methylbutanoic acid has a pleasantly sweet, fruity odor while (R)-2-methylbutanoic acid has a pervasive, cheesy, sweaty odor. Ethylmethylacetic acid exists in all eukaryotes, ranging from yeast to plants to humans. It Is found in a number of different plants and foods, such as safflowers, bilberries, and highbush blueberries. Ethylmethylacetic acid has also been detected in beer, brandy, coffee, cranberries, rum, strawberries, vinegar, whiskey, pepper (C. frutescens), orange bell peppers, yellow bell peppers, evergreen blackberries, and red bell peppers. Ethylmethylacetic acid/2-Methyl butanoic acid has been detected in human saliva has been linked to the presence of several mouth-related diseases such as halitosis and submandibular abcesses (PMID: 31426356 ). 2-Methyl butanoic acid is one of several acidic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methybutyric acidChEBI
alpha-Methyl butyric acidChEBI
alpha-Methylbutyric acidChEBI
Butane-2-carboxylic acidChEBI
Methylethylacetic acidChEBI
2-Methylbutyric acidKegg
2-MethybutyrateGenerator
a-Methyl butyrateGenerator
a-Methyl butyric acidGenerator
alpha-Methyl butyrateGenerator
Α-methyl butyrateGenerator
Α-methyl butyric acidGenerator
a-MethylbutyrateGenerator
a-Methylbutyric acidGenerator
alpha-MethylbutyrateGenerator
Α-methylbutyrateGenerator
Α-methylbutyric acidGenerator
Butane-2-carboxylateGenerator
MethylethylacetateGenerator
2-MethylbutyrateGenerator
EthylmethylacetateGenerator
(+/-)-2-methylbutyrateHMDB
(+/-)-2-methylbutyric acidHMDB
2-EthylpropionateHMDB
2-Ethylpropionic acidHMDB
2-Methyl butyrateHMDB
2-Methyl butyric acidHMDB
2-MethylbutanoateHMDB, Generator
2-Methylbutanoic acidHMDB
D-2-Methyl butyrateHMDB
D-2-Methyl butyric acidHMDB
DL-2-Methy butyrateHMDB
DL-2-Methy butyric acidHMDB
DL-2-MethylbutyrateHMDB
DL-2-Methylbutyric acidHMDB
2-Methylbutyrate, (+-)-isomerMeSH, HMDB
2-Methylbutyrate, sodium saltMeSH, HMDB
RS-2-MethylbutyrateMeSH, HMDB
Ethylmethylacetic acidChEBI
Chemical FormulaC5H10O2
Average Molecular Weight102.13
Monoisotopic Molecular Weight102.0681
IUPAC Name2-methylbutanoic acid
Traditional Name(+-)-2-methylbutyrate
CAS Registry Number116-53-0
SMILES
CCC(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyWLAMNBDJUVNPJU-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
  • 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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility45 mg/mL at 20 °CNot Available
logP1.18HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.47ALOGPS
logP1.46ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m³·mol⁻¹ChemAxon
Polarizability10.98 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)splash10-05i0-9000000000-5202133990304f535e3e2015-03-01View Spectrum
GC-MS2-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-05i3-9000000000-0aaa78177c0a6f4e0f30Spectrum
GC-MS2-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-05i3-9000000000-0aaa78177c0a6f4e0f30Spectrum
Predicted GC-MS2-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9000000000-2909ffab0f5a63851edfSpectrum
Predicted GC-MS2-Methyl butanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05dr-9200000000-d03c368f82e8aafbbf2eSpectrum
Predicted GC-MS2-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-05i3-9000000000-1b5a036458bffab2edb22012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2cc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2cc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-3de63f631f358f44d6632021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-49980d35bd5bcf94041b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-9500000000-ebceed22ebf0c3f30cbf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-ee8b144eb008ebfb745c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-b0c600bc4b289c4f5f6d2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 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, 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
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002176
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008135
KNApSAcK IDC00029461
Chemspider ID8012
KEGG Compound IDC18319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6528
PubChem Compound8314
PDB IDNot Available
ChEBI ID37070
References
General References
  1. Monedeiro F, Milanowski M, Ratiu IA, Zmyslowski H, Ligor T, Buszewski B: VOC Profiles of Saliva in Assessment of Halitosis and Submandibular Abscesses Using HS-SPME-GC/MS Technique. Molecules. 2019 Aug 16;24(16). pii: molecules24162977. doi: 10.3390/molecules24162977. [PubMed:31426356 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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