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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002350
Secondary Accession Numbers
  • HMDB02350
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
Data?1582752245
Synonyms
ValueSource
1-HydroxyoctadecaneChEBI
1-OctadecanolChEBI
N-1-OctadecanolChEBI
N-OctadecanolChEBI
N-Octadecyl alcoholChEBI
Stearyl alcoholChEBI
StearylalkoholChEBI
Octadecan-1-olHMDB
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 KeyGLDOVTGHNKAZLK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.1e-06 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.2e-05 g/LALOGPS
logP10(8.27) g/LALOGPS
logP10(7.03) g/LChemAxon
logS10(-6.7) g/LALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.55 m³·mol⁻¹ChemAxon
Polarizability38.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.29731661259
DarkChem[M-H]-172.93831661259
DeepCCS[M+H]+171.77930932474
DeepCCS[M-H]-167.7630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OctadecanolCCCCCCCCCCCCCCCCCCO2623.1Standard polar33892256
OctadecanolCCCCCCCCCCCCCCCCCCO2074.6Standard non polar33892256
OctadecanolCCCCCCCCCCCCCCCCCCO2090.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octadecanol,1TMS,isomer #1CCCCCCCCCCCCCCCCCCO[Si](C)(C)C2150.3Semi standard non polar33892256
Octadecanol,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCO[Si](C)(C)C(C)(C)C2385.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Octadecanol GC-MS (1 TMS)splash10-004i-9505000000-d69a3d5dc9469813c3ea2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octadecanol EI-B (Non-derivatized)splash10-052f-9000000000-f288a18a6df1296b18be2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octadecanol EI-B (Non-derivatized)splash10-0a5c-9100000000-ef18c1dfe45ef20701732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octadecanol GC-MS (Non-derivatized)splash10-004i-9505000000-d69a3d5dc9469813c3ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octadecanol GC-EI-TOF (Non-derivatized)splash10-0f9j-9703000000-701cb0c2d83164bde2dd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-5940000000-062625d0a206d7fb18cd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanol GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9751000000-65a6a8ff9989fd5c127b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a5c-9100000000-92cb2d6dbb9a8285a5ac2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanol Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-014i-0290000000-9688b7c87e601e496fdd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanol Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00or-9400000000-6fd41093c532a09a9f032012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanol Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-004i-9000000000-b13f813efb4bd06991a72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanol EI-B (SHIMADZU QP-1000) , Positive-QTOFsplash10-052f-9000000000-f288a18a6df1296b18be2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0a5c-9100000000-3fcdbbf1125eb4dc0bb52012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 10V, Positive-QTOFsplash10-0uk9-0090000000-faeda7f0e485dafd8e762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 20V, Positive-QTOFsplash10-0uk9-4590000000-935f6099331b8f9b8e902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 40V, Positive-QTOFsplash10-052f-9620000000-46019e66a566afdec20e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 10V, Negative-QTOFsplash10-014i-0090000000-1ded600ce853d9f6a61b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 20V, Negative-QTOFsplash10-014i-0090000000-8cec2e360cb361b0157b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 40V, Negative-QTOFsplash10-0f9f-8970000000-eb74591d5b40e712980a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 10V, Positive-QTOFsplash10-00di-2090000000-15e4d1ab7a06183746002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 20V, Positive-QTOFsplash10-05fr-9130000000-106a61bccad2c908c5922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 40V, Positive-QTOFsplash10-0a4l-9000000000-89fd5ad6d936f9c465342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 10V, Negative-QTOFsplash10-014i-0090000000-d9a19bd8044281bb6bc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 20V, Negative-QTOFsplash10-014i-0090000000-a145e1813aabce86aa2f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanol 40V, Negative-QTOFsplash10-014i-5490000000-81e8fdada3a9caad12462021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012764
KNApSAcK IDC00029422
Chemspider ID7928
KEGG Compound IDD01924
BioCyc IDCPD-7873
BiGG IDNot Available
Wikipedia LinkStearyl_alcohol
METLIN ID6640
PubChem Compound8221
PDB IDNot Available
ChEBI ID32154
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:2241202 ]
  4. Kelson TL, Craft DA, Rizzo WB: Carrier detection for Sjogren-Larsson syndrome. J Inherit Metab Dis. 1992;15(1):105-11. [PubMed: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. [PubMed: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