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Showing NP-Card for 2-Arachidonyl glycerol ether (NP0339390)

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Record Information
Version2.0
Created at2024-09-11 21:35:40 UTC
Updated at2024-09-11 21:35:41 UTC
NP-MRD IDNP0339390
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Arachidonyl glycerol ether
Description2-Arachidonyl Glycerol ether, also known as noladin ether or 2-ag ether, belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail. Thus, 2-arachidonyl glycerol ether is considered to be a monoradylglycerol lipid molecule. 2-Arachidonyl Glycerol ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. M at the CB1 and peripheral cannabinoid (CB2) receptors, respectively, and displays the typical tetrad of CB activities in mice.1. 2-Arachidonyl glycerol ether was first documented in 2001 (PMID: 11259648). G per eye.3 2-Arachidonyl Glycerol ether increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork (PMID: 22309979) (PMID: 22728691) (PMID: 23386378).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339390 (2-Arachidonyl glycerol ether)


  Mrv0541 02271200292D          

 26 25  0  0  0  0            999 V2000
    4.1637   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5927   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7361   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4506   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1651   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8796   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5940   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3085   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0230   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7374   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4519   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1664   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8809   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5954   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3098   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0243   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7388   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4532   -9.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8822   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -10.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5967   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8822  -10.6979    0.0000 O   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
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
M  END
Download

3D MOL for NP0339390 (2-Arachidonyl glycerol ether)

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3D SDF for NP0339390 (2-Arachidonyl glycerol ether)

  Mrv0541 02271200292D          

 26 25  0  0  0  0            999 V2000
    4.1637   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5927   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7361   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4506   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1651   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8796   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5940   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3085   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0230   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7374   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4519   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1664   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8809   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5954   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3098   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0243   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7388   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4532   -9.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8822   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -10.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5967   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8822  -10.6979    0.0000 O   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
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
CUJUUWXZAQHCNC-DOFZRALJSA-N

> <FORMULA>
C23H40O3

> <MOLECULAR_WEIGHT>
364.5619

> <EXACT_MASS>
364.297745146

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.15298518630716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
5.793423509

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.00367922115326

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.302551969678213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.972193248359324

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
117.2233

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-arachidonyl-glycerol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339390 (2-Arachidonyl glycerol ether)
Download
PDB for NP0339390 (2-Arachidonyl glycerol ether)
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       7.772 -16.889   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.106 -17.659   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.440 -16.889   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.773 -17.659   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.107 -16.889   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.441 -17.659   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.774 -17.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.108 -16.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.442 -17.659   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.775 -17.659   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.109 -16.889   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.443 -17.659   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.776 -17.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.110 -16.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.444 -17.659   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.778 -17.659   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.111 -16.889   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.445 -17.659   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.779 -16.889   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.112 -17.659   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      34.446 -16.889   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      35.780 -17.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.113 -16.889   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.780 -19.199   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      38.447 -17.659   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      37.113 -19.969   0.000  0.00  0.00           O+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                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

Download
3D PDB for NP0339390 (2-Arachidonyl glycerol ether)
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SMILES for NP0339390 (2-Arachidonyl glycerol ether)
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO
Download
INCHI for NP0339390 (2-Arachidonyl glycerol ether)
InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
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Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-Icosatetraenyl-2-glyceryl etherChEBI
2-(5Z,8Z,11Z,14Z-Eicosatetraenyl)-sn-glycerolChEBI
2-AG etherChEBI
2-O-(5Z,8Z,11Z,14Z)-EicosatetraenylglycerolChEBI
5Z,8Z,11Z,14Z-Eicosatetraen-2-glyceryl etherChEBI
Noladin etherChEBI
2-ArachidonylglycerolHMDB
HU-310HMDB
NoladinHMDB
2-Arachidonyl glyceryl etherHMDB
Chemical FormulaC23H40O3
Average Mass364.5619 Da
Monoisotopic Mass364.29775 Da
IUPAC Name2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol
Traditional Name2-arachidonyl-glycerol
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO
InChI Identifier
InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI KeyCUJUUWXZAQHCNC-DOFZRALJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassEndocannabinoids  
Sub ClassNot Available
Direct ParentEndocannabinoids  
Alternative Parents
Substituents
  • 2-arachidonylglyceryl-ether-skeleton
    • 

  • Monoalkylglycerol
    • 

  • Monoradylglycerol
    • 

  • Glycerolipid
    • 

  • Glycerol ether
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP6.13ALOGPS
logP5.79ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity117.22 m³·mol⁻¹ChemAxon
Polarizability45.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013657  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029627  
KNApSAcK IDNot Available
Chemspider ID4983515  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Arachidonyl_glyceryl_ether  
METLIN IDNot Available
PubChem Compound6483057  
PDB IDNot Available
ChEBI ID75913  
Good Scents IDNot Available
References
General References
  1. Hanus L, Abu-Lafi S, Fride E, Breuer A, Vogel Z, Shalev DE, Kustanovich I, Mechoulam R: 2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci U S A. 2001 Mar 27;98(7):3662-5. doi: 10.1073/pnas.061029898.  Epub 2001 Mar 20. [PubMed:11259648  ] 
  2. Jones EK, Kirkham TC: Noladin ether, a putative endocannabinoid, enhances motivation to eat after acute systemic administration in rats. Br J Pharmacol. 2012 Jul;166(6):1815-21. doi: 10.1111/j.1476-5381.2012.01888.x. [PubMed:22309979  ] 
  3. Deshmukh RR, Sharma PL: Stimulation of accumbens shell cannabinoid CB(1) receptors by noladin ether, a putative endocannabinoid, modulates food intake and dietary selection in rats. Pharmacol Res. 2012 Sep;66(3):276-82. doi: 10.1016/j.phrs.2012.06.004. Epub 2012  Jun 21. [PubMed:22728691  ] 
  4. Shimizu T, Tanaka K, Yokotani K: Stimulatory and inhibitory roles of brain 2-arachidonoylglycerol in bombesin-induced central activation of adrenomedullary outflow in rats. J Pharmacol Sci. 2013;121(2):157-71. doi: 10.1254/jphs.12208fp. Epub 2013 Feb 2. [PubMed:23386378  ]