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Record Information
Version3.6
Creation Date2006-05-22 14:17:37 UTC
Update Date2016-02-11 01:05:22 UTC
HMDB IDHMDB02117
Secondary Accession NumbersNone
Metabolite Identification
Common NameOleamide
DescriptionOleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. The mechanism of action of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.
Structure
Thumb
Synonyms
ValueSource
(9Z)-9-OctadecenamideChEBI
(Z)-9-OctadecenamideChEBI
(Z)-Octadec-9-enoic acid amideChEBI
9-OctadecenamideChEBI
9Z-OctadecenamideChEBI
cis-9,10-OctadecenoamideChEBI
Oleic acid amideChEBI
Oleyl amideChEBI
OleylamideChEBI
(Z)-Octadec-9-enoate amideGenerator
Oleate amideGenerator
(9Z)-Octadec-9-enamideHMDB
(cis)-9-OctadecenoateHMDB
(cis)-9-Octadecenoic acidHMDB
(cis)-9-Octadecenoic acid amideHMDB
14C-Labeled oleamideHMDB
9,10-OctadecenamideHMDB
Adogen 73HMDB
Aliphatic amideHMDB
Amide OHMDB
Armid OHMDB
Armoslip CPHMDB
Crodamide OHMDB
Crodamide orHMDB
Diamide O 200HMDB
Diamit O 200HMDB
ElaidoylamideHMDB
ELDHMDB
Kemamide OHMDB
Octadecene amideHMDB
Petrac slip-ezeHMDB
Polydis TR 121HMDB
Slip-ezeHMDB
Tocris-0878HMDB
trans-9,10-OctadecenoamideHMDB
Unislip 1759HMDB
Chemical FormulaC18H35NO
Average Molecular Weight281.4766
Monoisotopic Molecular Weight281.271864747
IUPAC Name(9Z)-octadec-9-enamide
Traditional Nameoleamide
CAS Registry Number301-02-0
SMILES
CCCCCCCC\C=C/CCCCCCCC(N)=O
InChI Identifier
InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
InChI KeyInChIKey=FATBGEAMYMYZAF-KTKRTIGZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentFatty amides
Alternative Parents
Substituents
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.31e-05 mg/mLALOGPS
logP7.19ALOGPS
logP5.98ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)16.92ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity89.22 m3·mol-1ChemAxon
Polarizability37.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03784
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012436
KNApSAcK IDNot Available
Chemspider ID4446508
KEGG Compound IDC19670
BioCyc IDCPD6666-1
BiGG IDNot Available
Wikipedia LinkOleamide
NuGOwiki LinkHMDB02117
Metagene LinkHMDB02117
METLIN IDNot Available
PubChem Compound5283387
PDB IDNot Available
ChEBI ID116314
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:
FAAH
Uniprot ID:
O00519
Molecular weight:
63065.28
Reactions
Oleamide + Water → Oleic acid + Ammoniadetails
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:
FAAH2
Uniprot ID:
Q6GMR7
Molecular weight:
58303.115
Reactions
Oleamide + Water → Oleic acid + Ammoniadetails