Oleamide
Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumliates 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-regliated depression. The mechanism of action of oleamides sleep inducing effects is an area of current research. It is likely that oleamide interacts with mlitiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a flil agonist.
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB02117 (Oleamide)
C18H35NO
281.4766
281.271864747
(9Z)-octadec-9-enamide
oleamide
301-02-0
CCCCCCCCC=C/CCCCCCCC(N)=O
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-
FATBGEAMYMYZAF-KTKRTIGZSA-N
This compound belongs to the class of chemical entities known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
Chemical entities
Organic compounds
Lipids and lipid-like moleclies
Fatty Acyls
Fatty amides
Aliphatic acyclic compounds
Detected but not Quantified
Solid
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Not Available
Not Available
None
None
DB03784
Not Available
Not Available
Not Available
FDB012436
Not Available
4446508
C19670
CPD6666-1
Not Available
Oleamide
HMDB02117
HMDB02117
Not Available
5283387
Not Available
116314
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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
- 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. [PubMed:17016423 ]
- 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. [PubMed: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
- 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