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Showing NP-Card for Cervonoyl ethanolamide (NP0339370)

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Record Information
Version2.0
Created at2024-09-11 21:29:59 UTC
Updated at2024-09-11 21:30:00 UTC
NP-MRD IDNP0339370
Secondary Accession NumbersNone
Natural Product Identification
Common NameCervonoyl ethanolamide
DescriptionCervonoyl ethanolamide, also known as DHEA, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. Cervonoyl ethanolamide is a N-acylethanolamine. Cervonoyl ethanolamide is an extremely weak basic (essentially neutral) compound (based on its pKa). N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. It was first documented in 2000 (PMID: 11413487). NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli (PMID: 12560208) (PMID: 12692337) (PMID: 12056855) (PMID: 11997249).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339370 (Cervonoyl ethanolamide)


  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    4.3147  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8871  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0305  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7450  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4595  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1740  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4608  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8898  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0332  -15.6826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -14.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7477  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4622  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1767  -15.2701    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  2  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  2  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END
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3D MOL for NP0339370 (Cervonoyl ethanolamide)

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3D SDF for NP0339370 (Cervonoyl ethanolamide)

  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    4.3147  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8871  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0305  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7450  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4595  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1740  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4608  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8898  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0332  -15.6826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -14.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7477  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4622  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1767  -15.2701    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  2  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  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
CXWASNUDKUTFPQ-KUBAVDMBSA-N

> <FORMULA>
C24H36O3

> <MOLECULAR_WEIGHT>
372.5408

> <EXACT_MASS>
372.266445018

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
43.57822893811415

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
6.208256871666666

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.096551894146636

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7565682015002624

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
122.4506

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339370 (Cervonoyl ethanolamide)
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PDB for NP0339370 (Cervonoyl ethanolamide)
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       8.054 -29.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.388 -28.504   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.722 -29.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.055 -29.274   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.389 -28.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.723 -29.274   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.056 -29.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.390 -28.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.724 -29.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.057 -29.274   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.391 -28.504   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.725 -29.274   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.059 -29.274   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.392 -28.504   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.726 -29.274   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.060 -29.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.393 -28.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.727 -29.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.061 -29.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.394 -28.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.728 -29.274   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.062 -28.504   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      37.395 -29.274   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      36.062 -26.964   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      38.729 -28.504   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      40.063 -29.274   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      41.397 -28.504   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                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

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3D PDB for NP0339370 (Cervonoyl ethanolamide)
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SMILES for NP0339370 (Cervonoyl ethanolamide)
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO
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INCHI for NP0339370 (Cervonoyl ethanolamide)
InChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
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View in JSmol
Synonyms
ValueSource
8,11,14-EicosatrienoylethanolamideHMDB
DHEAHMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamideHMDB
2-Hydroxyethyl (7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acidGenerator
Chemical FormulaC24H36O3
Average Mass372.5408 Da
Monoisotopic Mass372.26645 Da
IUPAC Name2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
Traditional Name2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO
InChI Identifier
InChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyCXWASNUDKUTFPQ-KUBAVDMBSA-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 fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP6.39ALOGPS
logP6.21ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity122.45 m³·mol⁻¹ChemAxon
Polarizability43.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013627  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029604  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13828  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53245830  
PDB IDNot Available
ChEBI ID34488  
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. doi:  10.1152/ajpheart.00888.2002. Epub 2003 Jan 30. [PubMed:12560208  ] 
  3. Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. doi: 10.1104/pp.102.014936. [PubMed:12692337  ] 
  4. Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. doi: 10.1006/jmcc.2002.1533. [PubMed:12056855  ] 
  5. Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. doi:  10.1152/ajpcell.00471.2001. [PubMed:11997249  ]