Showing Compound Card for 3-Methyl butanoic acid (CDB005784)

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Record Information
Version1.0
Created at2020-04-27 16:56:15 UTC
Updated at2021-01-04 18:59:28 UTC
CannabisDB IDCDB005784
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Methyl butanoic acid
DescriptionIsovaleric acid, also known as 3-methylbutanoic acid or beta-methylbutyric 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. Isovaleric acid is also classified as a fatty acid. It exists as a colorless liquid that is sparingly soluble in water. Isovaleric acid exists in all living species, ranging from bacteria to plants to humans. It is frequently found in a wide variety of plants and essential oils. Isovaleric acid has a strong pungent cheesy or sweaty smell. It is a major component of strong foot odor as it is produced by skin bacteria metabolizing leucine (PMID: 16699586 ). An excess of isovaleric acid in wine is generally seen as a defect, as it can give wines a sweaty, leathery, or barnyard-like smell. In wine, isovaleric acid is produced by the spoilage yeast Brettanomyces. In small amounts isovaleric acid can smell smokey, spicy, or medicinal. Isovaleric acid is found in many different plants and foods such as apples, bananas, roasted barley, beer, blackberry fruit, brandy, cheese, sour cherry, cinnamon, cider, citrus fruits, cocoa, coffee, cornmint plants, fish, grapes, hops, milk, mushrooms, papaya, passion fruit, peaches, pears, peanuts, peas, celery, safflower, yellow bell peppers, black pepper, raspberries, rosemary, strawberry, spearmint, tea, tomatoes and valerian root. It has been proposed that isovaleric acid is the anticonvulsant agent in valerian (PMID: 15509234 ). Isovaleric acid has been shown to be a a protein kinase A (PKA) agonist and causes smooth muscle relaxation via the PKA pathway (PMID: 30560338 ). Isovaleric acid (along with isovalerylcarnitine) is eleveated in the serum of patients with isovaleric acidemia. Isovaleric acidemia (IVA) is a rare autosomal recessive disorder of leucine metabolism caused by a defective isovaleryl-CoA dehydrogenase (IVD) gene (PMID: 32505769). Health problems related to isovaleric acidemia range from very mild to life-threatening. In severe cases, the features of isovaleric acidemia become apparent within a few days after birth. The initial symptoms include poor feeding, vomiting, seizures, and lack of energy (lethargy). These symptoms sometimes progress to more serious medical problems, including seizures, coma, and possibly death. A characteristic sign of isovaleric acidemia is a distinctive odor of sweaty feet during acute illness. Isovaleric 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
3-Methyl-N-butyric acidChEBI
3-Methylbutanoic acidChEBI
3-MethylbuttersaeureChEBI
3-Methylbutyric acidChEBI
beta-Methylbutyric acidChEBI
Delphinic acidChEBI
Isobutylformic acidChEBI
Isopentanoic acidChEBI
Isopropylacetic acidChEBI
IsovalerateChEBI
Isovalerianic acidChEBI
IsovaleriansaeureChEBI
3-Methyl-N-butyrateGenerator
3-MethylbutanoateGenerator
3-MethylbutyrateGenerator
b-MethylbutyrateGenerator
b-Methylbutyric acidGenerator
beta-MethylbutyrateGenerator
Β-methylbutyrateGenerator
Β-methylbutyric acidGenerator
DelphinateGenerator
IsobutylformateGenerator
IsopentanoateGenerator
IsopropylacetateGenerator
IsovalerianateGenerator
3-Methyl butyric acidHMDB
3-Methylbutyric acid: isopropyl-acetateHMDB
3-Methylbutyric acid: isopropyl-acetic acidHMDB
3-Methyl-1-butanoic acidHMDB
Isovaleric acidKEGG
Chemical FormulaC5H10O2
Average Molecular Weight102.13
Monoisotopic Molecular Weight102.0681
IUPAC Name3-methylbutanoic acid
Traditional Nameisovaleric acid
CAS Registry Number503-74-2
SMILES
CC(C)CC(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyGWYFCOCPABKNJV-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-29.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40.7 mg/mLNot Available
logP1.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.26ALOGPS
logP1.21ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.99 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)splash10-03dl-9000000000-e7c77b2bc7f3ac5191e92015-03-01View Spectrum
GC-MS3-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfSpectrum
GC-MS3-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Spectrum
GC-MS3-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfSpectrum
GC-MS3-Methyl butanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Spectrum
Predicted GC-MS3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-2825512cee017b3ab87cSpectrum
Predicted GC-MS3-Methyl butanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059f-9200000000-628e11f1ffbaa913ef57Spectrum
Predicted GC-MS3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl butanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0gvo-9300000000-16b5d15d26810b72bb362012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-692791435c37fa74a6922012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b4c1b59653cd4d8036372012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b0f7e399edb7f95572ed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-c8be68873f336c8de6d62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-63b09019c280c88ee64d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a002012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-63b09019c280c88ee64d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-871b21c20bba686fb9152021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-6ce72c7a41bfb4bc1b2d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0nmi-9300000000-efcb74e7796ba9769f972021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e825f0aa9ab54c1695d32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-9ba126f982634fdc94062015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-afb863a56c8763c302512015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-244535e4070d536a29b32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9300000000-93ed2bc326380cb0d8802015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-44b2fa11a5a6daab8dd02015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-f59a47a684453302cbed2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-83176e54a19e36af76f22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-81052c8b00621fcf04432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-7900000000-fd28737d49ed09628cfa2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
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 NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)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 IDHMDB0000718
DrugBank IDDB03750
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001324
KNApSAcK IDC00001189
Chemspider ID10001
KEGG Compound IDC08262
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylbutanoic acid
METLIN ID109
PubChem Compound10430
PDB IDNot Available
ChEBI ID28484
References
General References
  1. Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. doi: 10.1139/w05-130. [PubMed:16699586 ]
  2. Eadie MJ: Could valerian have been the first anticonvulsant? Epilepsia. 2004 Nov;45(11):1338-43. doi: 10.1111/j.0013-9580.2004.27904.x. [PubMed:15509234 ]
  3. Blakeney BA, Crowe MS, Mahavadi S, Murthy KS, Grider JR: Branched Short-Chain Fatty Acid Isovaleric Acid Causes Colonic Smooth Muscle Relaxation via cAMP/PKA Pathway. Dig Dis Sci. 2019 May;64(5):1171-1181. doi: 10.1007/s10620-018-5417-5. Epub 2018 Dec 17. [PubMed:30560338 ]

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