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Record Information
Version2.0
Created at2022-09-08 19:08:09 UTC
Updated at2022-09-08 19:08:10 UTC
NP-MRD IDNP0272493
Secondary Accession NumbersNone
Natural Product Identification
Common Name(9z)-octadec-9-enimidic acid
DescriptionOleamide, also known as amide O or oleyl amide, 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. Thus, oleamide is considered to be a fatty amide lipid molecule. A fatty amide derived from oleic acid. (9z)-octadec-9-enimidic acid is found in Desmos cochinchinensis, Glycine max, Pseudo-nitzschia multistriata, Trypanosoma brucei and Vitis vinifera. (9z)-octadec-9-enimidic acid was first documented in 2001 (PMID: 11681856). Oleamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 17445087) (PMID: 24253045).
Structure
Thumb
Synonyms
ValueSource
(9Z)-9-OctadecenamideChEBI
(9Z)-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
Oleylamide, (e)-isomerHMDB
Chemical FormulaC18H35NO
Average Mass281.4766 Da
Monoisotopic Mass281.27186 Da
IUPAC Name(9Z)-octadec-9-enamide
Traditional Nameoleamide
CAS Registry NumberNot Available
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 KeyFATBGEAMYMYZAF-KTKRTIGZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Desmos cochinchinensisLOTUS Database
Glycine maxLOTUS Database
Pseudo-nitzschia multistriataLOTUS Database
Trypanosoma bruceiLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description 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
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity89.22 m³·mol⁻¹ChemAxon
Polarizability37.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002117
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012436
KNApSAcK IDNot Available
Chemspider ID4446508
KEGG Compound IDC19670
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleamide
METLIN IDNot Available
PubChem Compound5283387
PDB IDNot Available
ChEBI ID116314
Good Scents IDNot Available
References
General References
  1. Huitron-Resendiz S, Gombart L, Cravatt BF, Henriksen SJ: Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Exp Neurol. 2001 Nov;172(1):235-43. doi: 10.1006/exnr.2001.7792. [PubMed:11681856 ]
  2. Hiley CR, Hoi PM: Oleamide: a fatty acid amide signaling molecule in the cardiovascular system? Cardiovasc Drug Rev. 2007 Spring;25(1):46-60. doi: 10.1111/j.1527-3466.2007.00004.x. [PubMed:17445087 ]
  3. Izquierdo-Garcia JL, Naz S, Nin N, Rojas Y, Erazo M, Martinez-Caro L, Garcia A, de Paula M, Fernandez-Segoviano P, Casals C, Esteban A, Ruiz-Cabello J, Barbas C, Lorente JA: A Metabolomic Approach to the Pathogenesis of Ventilator-induced Lung Injury. Anesthesiology. 2014 Mar;120(3):694-702. doi: 10.1097/ALN.0000000000000074. [PubMed:24253045 ]
  4. LOTUS database [Link]