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Record Information
Version3.6
Creation Date2006-05-22 14:17:49 UTC
Update Date2016-02-11 01:05:35 UTC
HMDB IDHMDB02350
Secondary Accession NumbersNone
Metabolite Identification
Common NameOctadecanol
DescriptionOctadenol is a fatty alcohol present in human and is normally incorporated into plasmalogen lipids. Patients with the autosomal recessive form of rhizomelic chondrodysplasia punctata (AR-RCDP) have elevated octadenol levels, but tended to be normal in other generalized peroxisomal disorders such as neonatal adrenoleukodystrophy and Zellweger syndrome (peroxisomal disorders are deficient in the incorporation of fatty alcohol into plasmalogen lipids). (PMID: 8373640 ). Sjogren-Larsson syndrome is defined by the triad of ichthyosis, mental retardation, and spasticity, and patients accumulate fatty alcohols such as Octadenol in the plasma and cultured fibroblasts. (PMID: 2241202 ). Sjogren-Larsson syndrome (SLS) is an autosomal recessive disorder associated with reduced activity of the fatty alcohol: NAD+ oxidoreductase complex (FAO). SLS patients are specifically deficient in the fatty aldehyde dehydrogenase (FALDH) component of FAO. Measurement of FAO and FALDH detection for SLS, FAO and FALDH activities in cultured skin fibroblasts using the 18-carbon substrate Octadenol is useful for SLS carrier detection. (PMID: 1583866 ). Patients with Sjogren-Larsson syndrome accumulate long-chain fatty alcohol in plasma, with a greater relative accumulation of Octadenol. (PMID: 2666627 ).
Structure
Thumb
Synonyms
ValueSource
1-HydroxyoctadecaneChEBI
1-OctadecanolChEBI
N-1-OctadecanolChEBI
N-OctadecanolChEBI
N-Octadecyl alcoholChEBI
Octadecan-1-olChEBI
OctadecanolChEBI
StearylalkoholChEBI
Alcohol stearylicusHMDB
Alfol 18HMDB
atalco SHMDB
Octadecanol NFHMDB
Octadecyl alcoholHMDB
StearalHMDB
Stearic alcoholHMDB
StearolHMDB
Stearyl alcohol pureHMDB
Chemical FormulaC18H38O
Average Molecular Weight270.4937
Monoisotopic Molecular Weight270.292265838
IUPAC Nameoctadecan-1-ol
Traditional Namestearyl alcohol
CAS Registry Number112-92-5
SMILES
CCCCCCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3
InChI KeyInChIKey=GLDOVTGHNKAZLK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point59.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.1e-06 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.22e-05 mg/mLALOGPS
logP8.27ALOGPS
logP7.03ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.55 m3·mol-1ChemAxon
Polarizability38.65 Å3ChemAxon
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)splash10-004i-9505000000-d69a3d5dc9469813c3eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0290000000-9688b7c87e601e496fddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00or-9400000000-6fd41093c532a09a9f03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-b13f813efb4bd06991a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-052f-9000000000-f288a18a6df1296b18beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a5c-9100000000-3fcdbbf1125eb4dc0bb5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a5c-9100000000-92cb2d6dbb9a8285a5acView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Feces
  • Saliva
Tissue Location
  • Adipose Tissue
  • Bladder
  • Brain
  • Eye Lens
  • Fetus
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Mouth
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Plasmalogen SynthesisSMP00479Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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 IDFDB012764
KNApSAcK IDC00029422
Chemspider ID7928
KEGG Compound IDD01924
BioCyc IDCYCLOHEXANOL
BiGG IDNot Available
Wikipedia LinkOctadecan-1-ol
NuGOwiki LinkHMDB02350
Metagene LinkHMDB02350
METLIN ID6640
PubChem Compound8221
PDB IDNot Available
ChEBI ID32154
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rizzo WB, Craft DA: Sjogren-Larsson syndrome: accumulation of free fatty alcohols in cultured fibroblasts and plasma. J Lipid Res. 2000 Jul;41(7):1077-81. [10884288 ]
  2. Rizzo WB, Craft DA, Judd LL, Moser HW, Moser AB: Fatty alcohol accumulation in the autosomal recessive form of rhizomelic chondrodysplasia punctata. Biochem Med Metab Biol. 1993 Aug;50(1):93-102. [8373640 ]
  3. Koone MD, Rizzo WB, Elias PM, Williams ML, Lightner V, Pinnell SR: Ichthyosis, mental retardation, and asymptomatic spasticity. A new neurocutaneous syndrome with normal fatty alcohol:NAD+ oxidoreductase activity. Arch Dermatol. 1990 Nov;126(11):1485-90. [2241202 ]
  4. Kelson TL, Craft DA, Rizzo WB: Carrier detection for Sjogren-Larsson syndrome. J Inherit Metab Dis. 1992;15(1):105-11. [1583866 ]
  5. Rizzo WB, Dammann AL, Craft DA, Black SH, Tilton AH, Africk D, Chaves-Carballo E, Holmgren G, Jagell S: Sjogren-Larsson syndrome: inherited defect in the fatty alcohol cycle. J Pediatr. 1989 Aug;115(2):228-34. [2666627 ]

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