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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:50 UTC
Update Date2019-07-23 06:08:56 UTC
HMDB IDHMDB0031525
Secondary Accession Numbers
  • HMDB31525
Metabolite Identification
Common Name(S)-2-Methylbutanal
Description(S)-2-Methylbutanal belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms (S)-2-Methylbutanal is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (S)-2-Methylbutanal has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and tea. This could make (S)-2-methylbutanal a potential biomarker for the consumption of these foods (S)-2-Methylbutanal, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease and ulcerative colitis; (S)-2-methylbutanal has also been linked to the inborn metabolic disorder celiac disease. A 2-methylbutanal that has S configuration.
Structure
Data?1563862136
Synonyms
ValueSource
(2S)-2-MethylbutyraldehydeChEBI
(2S)-2-Methylbutyric aldehydeChEBI
(S)-2-MethylbutyraldehydeChEBI
(S)-2-Methylbutyric aldehydeChEBI
(S)-alpha-Methylbutyric aldehydeChEBI
(S)-a-Methylbutyric aldehydeGenerator
(S)-Α-methylbutyric aldehydeGenerator
(+)(S)-2-MethylbutanalHMDB
(+)-2-MethylbutanalHMDB
(+)-2-MethylbutyraldehydeHMDB
(2S)-2-MethylbutanalHMDB
(RS)-2-MethylbutanalHMDB
(S)-(+)-2-MethylbutanalHMDB
(S)-2-MethylbutanalHMDB
(±)-2-MethylbutanalHMDB
(±)-2-MethylbutyraldehydeHMDB
2-EthylpropanalHMDB
2-FormylbutaneHMDB
2-MethylbutanalHMDB
2-MethylbutyraldehydeHMDB
2-Methylbutyric aldehydeHMDB
alpha-Methyl-n-butanalHMDB
alpha-MethylbutanalHMDB
alpha-MethylbutyraldehydeHMDB
alpha-Methylbutyric aldehydeHMDB
α-Methyl-n-butanalHMDB
α-MethylbutanalHMDB
α-MethylbutyraldehydeHMDB
α-Methylbutyric aldehydeHMDB
Chemical FormulaC5H10O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
IUPAC Name(2S)-2-methylbutanal
Traditional Name(2S)-2-methylbutanal
CAS Registry Number1730-97-8
SMILES
CC[C@H](C)C=O
InChI Identifier
InChI=1S/C5H10O/c1-3-5(2)4-6/h4-5H,3H2,1-2H3/t5-/m0/s1
InChI KeyBYGQBDHUGHBGMD-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentShort-chain aldehydes
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility21 g/LALOGPS
logP1.19ALOGPS
logP1.31ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)16.26ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.52 m³·mol⁻¹ChemAxon
Polarizability10.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-030ca6564fc322c12b94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-390a4b3c076ffaaa9654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9000000000-cdf0813b6616fa1c4d43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-3fca650fda89a084ab7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-688dccbda58eb29796c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-f57c47d0ebb97da44ae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-e84563fbce9f6e06a7d8Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified0-9713.739 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 and Quantified0-135527.942 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  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 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008128
KNApSAcK IDNot Available
Chemspider ID5342102
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6971249
PDB IDNot Available
ChEBI ID88414
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .