NP-MRD: Showing NP-Card for Cervonoyl ethanolamide (NP0339370)

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Record Information

Version

2.0

Created at

2024-09-11 21:29:59 UTC

Updated at

2024-09-11 21:30:00 UTC

NP-MRD ID

NP0339370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cervonoyl ethanolamide

Description

Cervonoyl 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. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli.

Structure

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
8,11,14-Eicosatrienoylethanolamide	HMDB
DHEA	HMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	HMDB
2-Hydroxyethyl (7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid	Generator

Chemical Formula

C₂₄H₃₆O₃

Average Mass

372.5408 Da

Monoisotopic Mass

372.26645 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not 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 Key

CXWASNUDKUTFPQ-KUBAVDMBSA-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
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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	6.39	ALOGPS
logP	6.21	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	122.45 m³·mol⁻¹	ChemAxon
Polarizability	43.58 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

HMDB0013627

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029604

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53245830

PDB ID

Not Available

ChEBI ID

34488

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cervonoyl ethanolamide (NP0339370)

MOL for NP0339370 (Cervonoyl ethanolamide)

3D MOL for NP0339370 (Cervonoyl ethanolamide)

3D SDF for NP0339370 (Cervonoyl ethanolamide)

3D-SDF for NP0339370 (Cervonoyl ethanolamide)

PDB for NP0339370 (Cervonoyl ethanolamide)

3D PDB for NP0339370 (Cervonoyl ethanolamide)

SMILES for NP0339370 (Cervonoyl ethanolamide)

INCHI for NP0339370 (Cervonoyl ethanolamide)

Structure for NP0339370 (Cervonoyl ethanolamide)

3D Structure for NP0339370 (Cervonoyl ethanolamide)