Arachidonoyl serinol (CHEM041406)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:12 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041406
Identification
Common NameArachidonoyl serinol
ClassSmall Molecule
Description2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor (PMID: 8954083, 9399597). Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol (PMID: 8893848). Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG (PMID: 9399597).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[(2-Hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamideHMDB
Chemical FormulaC23H39NO3
Average Molecular Mass377.561 g/mol
Monoisotopic Mass377.293 g/mol
CAS Registry Number183718-70-9
IUPAC Name(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide
Traditional NameAA dihydroxypropylamine
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO
InChI IdentifierInChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-
InChI KeyQHELXIATGZYOIB-DOFZRALJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0023 g/LALOGPS
logP5.35ALOGPS
logP4.68ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)-0.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity118.93 m³·mol⁻¹ChemAxon
Polarizability45.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-009e-8394000000-ee975369d3eb3fd9c364Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0avi-8291330000-6d7f0c815e7f37d353e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-3039000000-f862936c3f34b1dec568Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022l-9253000000-5d214947ccbaa7dd64fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9440000000-45a9bf0530671947f808Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-250c1e3347cdf3a2b1caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-4019000000-05fcf810b81f91aa4bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9110000000-f847e55771698d03c31dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-7149000000-2c9afb8661bb65299aedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9111000000-f2e0dce0e74bd4b489adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9100000000-e117b29e6bf0fd5d944eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-d2bf266ec49b9577dcffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-3039000000-b851578cb8583b68067aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9112000000-80adfac02ed1365cf330Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013650
FooDB IDFDB029620
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8771144
ChEBI ID332319
PubChem Compound ID10595770
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sugiura T, Kodaka T, Kondo S, Tonegawa T, Nakane S, Kishimoto S, Yamashita A, Waku K: 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma x glioma hybrid NG108-15 cells. Biochem Biophys Res Commun. 1996 Dec 4;229(1):58-64.
2. Sugiura T, Kodaka T, Kondo S, Nakane S, Kondo H, Waku K, Ishima Y, Watanabe K, Yamamoto I: Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem. 1997 Oct;122(4):890-5.
3. Khanolkar AD, Abadji V, Lin S, Hill WA, Taha G, Abouzid K, Meng Z, Fan P, Makriyannis A: Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. The lipid handbook with CD-ROM