You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2009-01-29 15:55:51 UTC
Update Date2017-09-27 08:26:36 UTC
HMDB IDHMDB0011619
Secondary Accession Numbers
  • HMDB11619
Metabolite Identification
Common NameArachidyl alcohol
DescriptionArachidyl alcohol, also 1-icosanol, is a waxy substance used as an emollient in cosmetics. It is a straight-chain fatty alcohol (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
1-EicosanolChEBI
Arachidic alcoholChEBI
Eicosan-1-olChEBI
Eicosyl alcoholChEBI
1-IcosanolHMDB
1-Icosanol (acd/name 4.0)HMDB
1-PrydroxyeicosaneHMDB
Arachic alcoholHMDB
EicosanolHMDB
Eicosanol-(1)HMDB
N-1-EicosanolHMDB
N-EicosanolHMDB
Chemical FormulaC20H42O
Average Molecular Weight298.5469
Monoisotopic Molecular Weight298.323565966
IUPAC Nameicosan-1-ol
Traditional Namearachidyl alcohol
CAS Registry Number629-96-9
SMILES
CCCCCCCCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C20H42O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21/h21H,2-20H2,1H3
InChI KeyBTFJIXJJCSYFAL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point66.1 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.7e-05 g/LALOGPS
logP8.9ALOGPS
logP7.92ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity95.75 m³·mol⁻¹ChemAxon
Polarizability42.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4i-5409000000-bcc2ca6cbba222bc03edView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-5409000000-bcc2ca6cbba222bc03edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0090000000-08798f344bb713c4c3c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3490000000-4bed532a3e1541b9e4d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9750000000-a204caab6e6a6561e0a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-d3a8abd3d7e3c54c969fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-f77972729fcd30226947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mp-8790000000-4dd3883951c290d5d68fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a5c-9100000000-f0f5bfb9ac4264e2cd89View 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 Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB007106
KNApSAcK IDNot Available
Chemspider ID11898
KEGG Compound IDNot Available
BioCyc IDCPD-7869
BiGG IDNot Available
Wikipedia Linkarachidyl alcohol
METLIN IDNot Available
PubChem Compound12404
PDB IDNot Available
ChEBI ID545111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
Gene Name:
AGPS
Uniprot ID:
O00116
Molecular weight:
72911.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of saturated fatty acyl-CoA with chain length C16 or C18 to fatty alcohols.
Gene Name:
FAR1
Uniprot ID:
Q8WVX9
Molecular weight:
59356.25
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:
FAR2
Uniprot ID:
Q96K12
Molecular weight:
59437.92
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:
AWAT1
Uniprot ID:
Q58HT5
Molecular weight:
37758.815
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:
AWAT2
Uniprot ID:
Q6E213
Molecular weight:
38093.25