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Record Information
Version3.6
Creation Date2007-04-12 20:14:15 UTC
Update Date2016-02-11 01:07:20 UTC
HMDB IDHMDB06007
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsopentanol
DescriptionIsopentanol or Isoamyl alcohol is one of several isomers of amyl alcohol. It is a by-product of gut microbial fermentation (PMID: 17452087 ). It can be produced by 3-methylbutanal reductase (EC 1.1.1.265) from 3 methylbutanal. Isoamyl alcohol is the major higher chain alcohol in alcoholic beverages and is present in cider, mead, beer, wine, and spirits to varying degrees, being obtained by the fermentation of starches. Isopentanol has been shown to induce expression of CYP3A and CYP2E1 in human liver (PMID: 7574728 ).
Structure
Thumb
Synonyms
ValueSource
Isoamyl alcoholKegg
Isopentyl alcoholKegg
1-Hydroxy-3-methylbutaneHMDB
2-Methyl-4-butanolHMDB
3-Methyl-1-butanolHMDB
3-Methyl-butan-(1)-olHMDB
3-Methyl-butanolHMDB
3-Methylbutan-1-olHMDB
3-MethylbutanoIHMDB
3-MethylbutanolHMDB
Butan-1-ol, 3-methylHMDB
Fermentation amyl alcoholHMDB
Fusel oilHMDB
I-amyl alcoholHMDB
iso-Amyl alcoholHMDB
iso-AmylalkoholHMDB
Isoamyl alcohol (3-methyl butanol)HMDB
Isoamyl alcohol (natural)HMDB
Isoamyl alkoholHMDB
IsoamylalcoholHMDB
IsoamylolHMDB
Isobutyl carbinolHMDB
IsobutylcarbinolHMDB
Isopentan-1-olHMDB
Methyl-3-butan-1-olHMDB
Primary isoamyl alcoholHMDB
Chemical FormulaC5H12O
Average Molecular Weight88.1482
Monoisotopic Molecular Weight88.088815006
IUPAC Name3-methylbutan-1-ol
Traditional Nameisoamyl alcohol
CAS Registry Number123-51-3
SMILES
CC(C)CCO
InChI Identifier
InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
InChI KeyInChIKey=PHTQWCKDNZKARW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassPrimary alcohols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-117.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.7 mg/mL at 25 °CNot Available
LogP1.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility38.0 mg/mLALOGPS
logP1.33ALOGPS
logP1.09ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)17.17ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.68 m3·mol-1ChemAxon
Polarizability11.03 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-370bf1c231476fa54243View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 71.55 ppmChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0 - 49.18 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02296
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008131
KNApSAcK IDNot Available
Chemspider ID29000
KEGG Compound IDC07328
BioCyc IDCPD-7032
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06007
Metagene LinkHMDB06007
METLIN IDNot Available
PubChem Compound31260
PDB IDIP3
ChEBI ID15837
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boumba VA, Ziavrou KS, Vougiouklakis T: Biochemical pathways generating post-mortem volatile compounds co-detected during forensic ethanol analyses. Forensic Sci Int. 2008 Jan 30;174(2-3):133-51. Epub 2007 Apr 23. [17452087 ]
  2. Kostrubsky VE, Strom SC, Wood SG, Wrighton SA, Sinclair PR, Sinclair JF: Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Arch Biochem Biophys. 1995 Oct 1;322(2):516-20. [7574728 ]

Enzymes

General function:
Involved in aspartic-type endopeptidase activity
Specific function:
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of blood pressure and increased sodium retention by the kidney
Gene Name:
REN
Uniprot ID:
P00797
Molecular weight:
45057.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]