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Record Information
Version4.0
Creation Date2007-05-23 11:08:59 UTC
Update Date2017-10-23 19:04:21 UTC
HMDB IDHMDB0006478
Secondary Accession Numbers
  • HMDB06478
Metabolite Identification
Common NameIso-Valeraldehyde
Descriptioniso-Valeraldehyde is an oxygenated (aldehyde) volatile organic compounds (VOC), normally found in humans, particularly in the gut. iso-Valeraldehyde is a leucine degradation product that has been found in elevated concentrations in some cases of hepatic encephalopathy, however not significantly. Fermentation of carbohydrates in the gut produces ethanoic, propionic, butanoic, pentanoic, and hexanoic acid acids, particularly by Bacteroides, although it is possible that some of the iso-Valeraldehyde is of dietetic origin. iso-Valeraldehyde has been found to be a normal component of the chemical profile of cheddar cheese, spirits (beer, rum, sake, wine). (PMID: 17314143 , 18275147 , 18175918 , 16899660 ).
Structure
Thumb
Synonyms
ValueSource
3-MethylbutyraldehydeChEBI
beta-MethylbutanalChEBI
iso-C4H9CHOChEBI
Isoamyl aldehydeChEBI
IsopentaldehydeChEBI
IsovaleralChEBI
IsovaleraldehydeChEBI
IsovalerylaldehydeChEBI
b-MethylbutanalGenerator
β-methylbutanalGenerator
2-Methylbutanal-4HMDB
3-Methyl-1-butanalHMDB
3-Methyl-butanalHMDB
3-Methyl-butyraldehydeHMDB
3-Methylbutan-1-alHMDB
3-MethylbutanalHMDB
IsoamylaldehydeHMDB
IsopentanalHMDB
Isovaleric aldehydeHMDB
Methyl butanalHMDB
Chemical FormulaC5H10O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
IUPAC Name3-methylbutanal
Traditional Nameisovaleraldehyde
CAS Registry Number590-86-3
SMILES
CC(C)CC=O
InChI Identifier
InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
InChI KeyYGHRJJRRZDOVPD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Hepatobiliary disorders:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-51 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility14 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17 g/LALOGPS
logP1.29ALOGPS
logP1.05ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.49 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-3a38c8f6150bf1f43e74View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5a3fd4f38dc36ebe58a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-4b322dc8237378d93057View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-7f4ac528265c8b3bf3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-6e4f25dc68765a0e52caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-809684cd2152204e911fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-3a38c8f6150bf1f43e74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5a3fd4f38dc36ebe58a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e49940View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d150View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c23464View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e49940View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d150View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c23464View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-881fcc89b0f579b40793View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 (0.0-0.34) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified14.9 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 4.88 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.24 (0.0-1.3) uMAdult (>18 years old)BothHepatic encephalopathy details
Cerebrospinal Fluid (CSF)Detected and Quantified290.0 uMAdult (>18 years old)BothHepatic encephalopathy details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
FecesDetected and Quantified0 - 97.85 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Hepatic encephalopathy
  1. Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed:7320160 ]
  2. Marshall AW, DeSouza M, Morgan MY: Plasma 3-methylbutanal in man and its relationship to hepatic encephalopathy. Clin Physiol. 1985 Feb;5(1):53-62. [PubMed:4038637 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003285
KNApSAcK IDNot Available
Chemspider ID11065
KEGG Compound IDC07329
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11552
PDB IDNot Available
ChEBI ID16638
References
Synthesis ReferenceRoelen, O. Synthesis of aldehydes and derivatives from olefins, carbon monoxide, and hydrogen. Angew. Chem. (1948), A60 62. CAN 44:46679 AN 1950:46679
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Sampaio OM, Reche RV, Franco DW: Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification. J Agric Food Chem. 2008 Mar 12;56(5):1661-8. doi: 10.1021/jf0726841. Epub 2008 Feb 15. [PubMed:18275147 ]
  3. Tanimoto S, Matsumoto H, Fujii K, Ohdoi R, Sakamoto K, Yamane Y, Miyake M, Shimoda M, Osajima Y: Enzyme inactivation and quality preservation of sake by high-pressure carbonation at a moderate temperature. Biosci Biotechnol Biochem. 2008 Jan;72(1):22-8. Epub 2008 Jan 7. [PubMed:18175918 ]
  4. Whetstine ME, Drake MA, Broadbent JR, McMahon D: Enhanced nutty flavor formation in cheddar cheese made with a malty Lactococcus lactis adjunct culture. J Dairy Sci. 2006 Sep;89(9):3277-84. [PubMed:16899660 ]