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Showing Compound Ethyl 3-hydroxyisovalerate (FDB007451)

Record Information
Version1.0
Creation date2010-04-08 22:07:37 UTC
Update date2025-11-18 23:04:51 UTC
Primary IDFDB007451
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEthyl 3-hydroxyisovalerate
Description3-hydroxyisovaleric acid, also known as beta-hydroxy-beta-methylbutyrate or 3-hydroxy-3-methylbutyric acid, is a member of the class of compounds known as hydroxy fatty acids. Hydroxy fatty acids are fatty acids in which the chain bears a hydroxyl group. Thus, 3-hydroxyisovaleric acid is considered to be a fatty acid lipid molecule. 3-hydroxyisovaleric acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3-hydroxyisovaleric acid can be synthesized from isovaleric acid and butyric acid. 3-hydroxyisovaleric acid can also be synthesized into 3-hydroxyisovalerylcarnitine and 3-hydroxyisovaleryl-CoA. 3-hydroxyisovaleric acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as in human fibroblasts tissue. Within the cell, 3-hydroxyisovaleric acid is primarily located in the cytoplasm (predicted from logP). Moreover, 3-hydroxyisovaleric acid is found to be associated with 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-Methylglutaconic aciduria type I, biotinidase deficiency, and lung Cancer. 3-hydroxyisovaleric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number18267-36-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-Hydroxy-3-methylbutyric acidChEBI
3-Hydroxy-isovaleric acidChEBI
3-Methyl-3-hydroxybutyric acidChEBI
3-OH-Isovaleric acidChEBI
beta-Hydroxy-beta-methylbutyric acidChEBI
beta-Hydroxyisovaleric acidChEBI
HMBChEBI
HMB-D6ChEBI
3-Hydroxy-3-methylbutyrateGenerator
3-Hydroxy-isovalerateGenerator
3-Methyl-3-hydroxybutyrateGenerator
3-OH-IsovalerateGenerator
b-Hydroxy-b-methylbutyrateGenerator
b-Hydroxy-b-methylbutyric acidGenerator
beta-Hydroxy-beta-methylbutyrateGenerator
Β-hydroxy-β-methylbutyrateGenerator
Β-hydroxy-β-methylbutyric acidGenerator
b-HydroxyisovalerateGenerator
b-Hydroxyisovaleric acidGenerator
beta-HydroxyisovalerateGenerator
Β-hydroxyisovalerateGenerator
Β-hydroxyisovaleric acidGenerator
3-HydroxyisovalerateGenerator
beta Hydroxy beta methylbutyrateHMDB
beta-Hydroxy beta-methylbutyrateHMDB
3-Hydroxy-3-methyl-butanoateHMDB
3-Hydroxy-3-methyl-butanoic acidHMDB
3-Hydroxy-3-methyl-butyric acidHMDB
3-Hydroxy-3-methylbutanoateHMDB
3-Hydroxy-3-methylbutanoic acidHMDB
3-Hydroxyisovaleric acidMeSH
3-Hydroxy-3-methylbutanoic acid ethyl esterdb_source
Predicted Properties
PropertyValueSource
Water Solubility384 g/LALOGPS
logP-0.12ALOGPS
logP-0.11ChemAxon
logS0.51ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.1 m³·mol⁻¹ChemAxon
Polarizability11.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10O3
IUPAC name3-hydroxy-3-methylbutanoic acid
InChI IdentifierInChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)
InChI KeyAXFYFNCPONWUHW-UHFFFAOYSA-N
Isomeric SMILESCC(C)(O)CC(O)=O
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
Classification
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Branched fatty acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-c15a37ad10e6379350aa2014-09-20View Spectrum
GC-MSEthyl 3-hydroxyisovalerate, non-derivatized, GC-MS Spectrumsplash10-000t-0900000000-56f9e1ee9e19bacfc939Spectrum
GC-MSEthyl 3-hydroxyisovalerate, non-derivatized, GC-MS Spectrumsplash10-000t-0900000000-56f9e1ee9e19bacfc939Spectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-0809a885d114ba6b21d7Spectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-6910000000-3573bf97996ef7107955Spectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl 3-hydroxyisovalerate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9300000000-e715db06e575104deccd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-885e3d959712c99982502012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0avi-9800000000-f0296f537bd22b26f1732012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-1900000000-b947237de42eec92a67e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-1381eacc487b12932a432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00dj-9000000000-f10c5afd9954f294ea912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9600000000-3b24b27c64b89a6a5b252021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-5900000000-2f664d0b967c87e7358c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zn9-9500000000-233e5cd462b504c09d3c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-62361f03b7c7a0d82bc42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9400000000-13e4ec512c0fde3123ab2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05tb-9200000000-96c7d7b3f54e7377a8752017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aba-9000000000-3cc71227974213e131c42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8900000000-a25104a0136877edd57e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-d2d6bcff64e0a706fc952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-65f5183bc669daba34f42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-9400000000-9721ad435e43092a072d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-13f5bd4a628f51aec8102021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-0eeab2c474971ae60e7b2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, 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
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID62571
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID69362
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0000754
CRC / DFC (Dictionary of Food Compounds) IDDBZ39-Y:PQH17-H
EAFUS IDNot Available
Dr. Duke ID3-HYDROXY-3-METHYLBUTANOIC-ACID-ETHYL-ESTER
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBeta-Hydroxy_beta-methylbutyric_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).