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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:34:56 UTC
Update Date2021-10-13 06:05:53 UTC
HMDB IDHMDB0030124
Secondary Accession Numbers
  • HMDB30124
Metabolite Identification
Common NamePrenol
DescriptionPrenol, also known as prenyl alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, prenol is considered to be a fatty alcohol. Prenol is a fruity, green, and herb tasting compound. Prenol has been detected, but not quantified in, several different foods, such as fats and oils, breakfast cereal, citrus, red raspberries (Rubus idaeus), and fruits. This could make prenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Prenol.
Structure
Data?1563861941
Synonyms
ValueSource
3-Methyl-2-buten-1-olChEBI
Prenyl alcoholKegg
2-Butenol, 3-methylHMDB
3,3-Dimethylallyl alcoholHMDB
3-Methyl-2-butene-1-olHMDB
3-Methyl-2-butenolHMDB
3-Methyl-2-butenyl alcoholHMDB
3-Methylbut-2-en-1-olHMDB, MeSH
3-Methylcrotyl alcoholHMDB
Butenol methylHMDB
Dimethylallyl alcoholHMDB
FEMA 3647HMDB
IsopentenolHMDB
Isopentenyl alcoholHMDB
Methyl-3-but-2-en-1-olHMDB
PrenolMeSH
Chemical FormulaC5H10O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
IUPAC Name3-methylbut-2-en-1-ol
Traditional Nameprenol
CAS Registry Number556-82-1
SMILES
CC(C)=CCO
InChI Identifier
InChI=1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3
InChI KeyASUAYTHWZCLXAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point138.00 to 174.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility40940 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.055 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility105 g/LALOGPS
logP10(0.92) g/LALOGPS
logP10(0.84) g/LChemAxon
logS10(0.09) g/LALOGPS
pKa (Strongest Acidic)16.4ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.38 m³·mol⁻¹ChemAxon
Polarizability10.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+116.90931661259
DarkChem[M-H]-110.81731661259
DeepCCS[M+H]+121.2730932474
DeepCCS[M-H]-119.09530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PrenolCC(C)=CCO1264.1Standard polar33892256
PrenolCC(C)=CCO753.3Standard non polar33892256
PrenolCC(C)=CCO766.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prenol,1TMS,isomer #1CC(C)=CCO[Si](C)(C)C924.0Semi standard non polar33892256
Prenol,1TBDMS,isomer #1CC(C)=CCO[Si](C)(C)C(C)(C)C1114.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-0a44046f690387f31abb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prenol GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9200000000-e30038d73acaca32e8152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00du-9000000000-43ea05d6aa3bb1c405932015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Prenol 10V, Positive-QTOFsplash10-0a4i-9000000000-cfa7bc85e1c8ea3bcf8b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prenol 20V, Positive-QTOFsplash10-0a4i-9000000000-c4f06301285596b1369f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prenol 40V, Positive-QTOFsplash10-0006-9000000000-42fe9455b931a6b2be412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 10V, Positive-QTOFsplash10-014r-9000000000-20ac52b15506504862ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 20V, Positive-QTOFsplash10-014i-9000000000-9a282ab109712e8d48fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 40V, Positive-QTOFsplash10-0uxr-9000000000-c04a5c1a5efac8e51c032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 10V, Negative-QTOFsplash10-000i-9000000000-49e99dc6b831ec0c9ed52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 20V, Negative-QTOFsplash10-0a4r-9000000000-5d400f8de64ab834b4eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 40V, Negative-QTOFsplash10-0aor-9000000000-39ee13a79168540789812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 10V, Positive-QTOFsplash10-014i-9000000000-ec566957fca13f183c852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 20V, Positive-QTOFsplash10-014l-9000000000-95c9eddc2bf9161e06d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 40V, Positive-QTOFsplash10-0006-9000000000-74e516f8a235417dee612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 10V, Negative-QTOFsplash10-000i-9000000000-2091e44a102d8284a8132021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 20V, Negative-QTOFsplash10-000i-9000000000-93a4ef8eb37f598b0b5e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenol 40V, Negative-QTOFsplash10-0uxu-9000000000-c946542e67b770bfb6222021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001927
KNApSAcK IDC00055661
Chemspider ID10700
KEGG Compound IDC01390
BioCyc IDPRENOL
BiGG IDNot Available
Wikipedia LinkPrenol
METLIN IDNot Available
PubChem Compound11173
PDB IDNot Available
ChEBI ID16019
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032261
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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Prenol → [(3-methylbut-2-en-1-yl)oxy]sulfonic aciddetails
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
Reactions
Prenol → 3,4,5-trihydroxy-6-[(3-methylbut-2-en-1-yl)oxy]oxane-2-carboxylic aciddetails