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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-07-25 00:12:51 UTC
Update Date2020-11-09 23:18:39 UTC
HMDB IDHMDB0013078
Secondary Accession Numbers
  • HMDB13078
Metabolite Identification
Common NameStearoylethanolamide
DescriptionStearoylethanolamide is an N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 , 12056855 , 12560208 , 11997249 ).
Structure
Data?1582753089
Synonyms
ValueSource
Monoethanolamine stearic acid amideChEBI
N-(2-Hydroxyethyl)stearamideChEBI
N-(Hydroxyethyl)stearamideChEBI
N-(Otadecanoyl)-ethanolamineChEBI
N-Octadecanoyl ethanolamineChEBI
N-OctadecanoylethanolamineChEBI
N-StearoylethanolamineChEBI
Stearamide meaChEBI
Stearic acid monoethanolamideChEBI
Stearic ethanolamideChEBI
Stearic monoethanolamideChEBI
Stearoyl ethanolamideChEBI
Stearoyl-eaChEBI
Stearoyl-ethanolamineChEBI
StearoylmonoethanolamideChEBI
Monoethanolamine stearate amideGenerator
Stearate monoethanolamideGenerator
N-(2-Hydroxyethyl)stearoylamideMeSH
StearoylethanolamideChEBI
Chemical FormulaC20H41NO2
Average Molecular Weight327.545
Monoisotopic Molecular Weight327.313729561
IUPAC NameN-(2-hydroxyethyl)octadecanamide
Traditional Namestearoyl-ethanolamine
CAS Registry Number111-57-9
SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)
InChI KeyOTGQIQQTPXJQRG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point98.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP6.67ALOGPS
logP5.87ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity99.3 m³·mol⁻¹ChemAxon
Polarizability44.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available186.42431661259
DarkChem[M-H]-PredictedNot Available185.68831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Stearoylethanolamide,1TMS,#12719.5193https://arxiv.org/abs/1905.12712
Stearoylethanolamide,1TMS,#22691.3374https://arxiv.org/abs/1905.12712
Stearoylethanolamide,1TBDMS,#12938.5881https://arxiv.org/abs/1905.12712
Stearoylethanolamide,1TBDMS,#22943.2222https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-7690000000-058feb2aa4543a87879c2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9451000000-4a8d0aaef26523b9d4252017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9015000000-04b06df4f18a2695af882016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9010000000-bf79ed793c07da4886fd2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-20c9688837b9850b45482016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1039000000-2d305f2c3bd765f78e402016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-7089000000-befa65d8e9e007e8b5762016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9020000000-1472dfcab540d83a08dc2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified15 +/- 11 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 IDFDB029286
KNApSAcK IDNot Available
Chemspider ID25958
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStearoylethanolamide
METLIN IDNot Available
PubChem Compound27902
PDB IDNot Available
ChEBI ID85299
Food Biomarker OntologyNot Available
VMH IDSTEETH
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. [PubMed:12692337 ]
  2. Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. [PubMed:12056855 ]
  3. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. Epub 2003 Jan 30. [PubMed:12560208 ]
  4. Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. [PubMed:11997249 ]