NP-MRD: Showing NP-Card for O-Arachidonoyl ethanolamine (NP0339388)

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Record Information

Version

2.0

Created at

2024-09-11 21:35:03 UTC

Updated at

2024-09-11 21:35:04 UTC

NP-MRD ID

NP0339388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

O-Arachidonoyl ethanolamine

Description

O-Arachidonoyl Ethanolamine, also known as O-AEA or virodhamine, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Thus, O-arachidonoyl ethanolamine is considered to be an other fatty acyl lipid molecule. O-Arachidonoyl Ethanolamine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. , As an ester instead of an amide, as in AEA.1,2,4 O-Arachidonoyl Ethanolamine has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor. This is in keeping with other observations that 2-AG is the primary endogenous CB1 receptor ligand. It was first documented in 2000 (PMID: 11413487). O-Arachidonoyl ethanolamine hydrochloride (O-AEA) is a recently isolated constituent of human and rat brain wherein the ethanolamine moiety is attached "backwards", as an ester instead of an amide, as in AEA.1,2,4 O-Arachidonoyl Ethanolamine has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271200292D          

 25 24  0  0  0  0            999 V2000
    4.9092   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6237   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3382   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0526   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7671   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4816   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1960   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9106   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6250   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3395   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0540   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7684   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4829   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1974   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9119   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6264   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3409   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0553   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7698   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4843   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1987   -9.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4843  -10.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9132   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6277   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3421   -9.4902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
DLHLOYYQQGSXCC-DOFZRALJSA-N

> <FORMULA>
C22H37NO2

> <MOLECULAR_WEIGHT>
347.5347

> <EXACT_MASS>
347.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
42.969143903201186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

> <ALOGPS_LOGP>
6.27

> <JCHEM_LOGP>
5.9360810583333325

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.226362426441638

> <JCHEM_POLAR_SURFACE_AREA>
52.32

> <JCHEM_REFRACTIVITY>
112.67289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
virodhamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       9.164 -16.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.498 -17.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.831 -16.945   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.165 -17.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.499 -16.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.832 -17.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.166 -17.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.500 -16.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.833 -17.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.167 -17.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.501 -16.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.834 -17.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.168 -17.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.502 -16.945   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.836 -17.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.169 -17.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.503 -16.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.837 -17.715   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.170 -16.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.504 -17.715   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      35.838 -16.945   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      34.504 -19.255   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      37.171 -17.715   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.505 -16.945   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      39.839 -17.715   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
Arachidonic acid-(2-aminoethyl)-ester	HMDB
O-AEA	HMDB
Virodhamine	HMDB
O-Arachidonyl ethanol amine	HMDB
O-Arachidonoyl ethanolamine	MeSH

Chemical Formula

C₂₂H₃₇NO₂

Average Mass

347.5347 Da

Monoisotopic Mass

347.28243 Da

IUPAC Name

2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Traditional Name

virodhamine

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN

InChI Identifier

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-

InChI Key

DLHLOYYQQGSXCC-DOFZRALJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Fatty Acyls (LMFA00000014 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.27	ALOGPS
logP	5.94	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	112.67 m³·mol⁻¹	ChemAxon
Polarizability	42.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013655

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029625

KNApSAcK ID

Not Available

Chemspider ID

4650158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Virodhamine

METLIN ID

Not Available

PubChem Compound

5712057

PDB ID

Not Available

ChEBI ID

418207

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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. [PubMed:16902246 ]
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. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]

Showing NP-Card for O-Arachidonoyl ethanolamine (NP0339388)

MOL for NP0339388 (O-Arachidonoyl ethanolamine)

3D MOL for NP0339388 (O-Arachidonoyl ethanolamine)

3D SDF for NP0339388 (O-Arachidonoyl ethanolamine)

3D-SDF for NP0339388 (O-Arachidonoyl ethanolamine)

PDB for NP0339388 (O-Arachidonoyl ethanolamine)

3D PDB for NP0339388 (O-Arachidonoyl ethanolamine)

SMILES for NP0339388 (O-Arachidonoyl ethanolamine)

INCHI for NP0339388 (O-Arachidonoyl ethanolamine)

Structure for NP0339388 (O-Arachidonoyl ethanolamine)

3D Structure for NP0339388 (O-Arachidonoyl ethanolamine)