NP-MRD: Showing NP-Card for Docosahexaenoyl Ethanolamide (NP0339391)

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Record Information

Version

2.0

Created at

2024-09-11 21:35:56 UTC

Updated at

2024-09-11 21:35:57 UTC

NP-MRD ID

NP0339391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Docosahexaenoyl Ethanolamide

Description

Docosahexaenoyl Ethanolamide, also known as anandamide (22:6, N-3) or DHEA, belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Thus, docosahexaenoyl ethanolamide is considered to be a fatty amide lipid molecule. Docosahexaenoyl Ethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    5.1298  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5587  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7022  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8456  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5601  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2746  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7036  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4180  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1325  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8470  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2759  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9904  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4194  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8483  -10.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -11.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5628  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2772  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9917  -10.8221    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 02271200292D          

 27 26  0  0  0  0            999 V2000
    5.1298  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5587  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7022  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8456  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5601  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2746  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7036  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4180  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1325  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8470  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2759  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9904  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4194  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8483  -10.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -11.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5628  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2772  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9917  -10.8221    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>
NP0339391

> <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)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
GEEHOLRSGZPBSM-KUBAVDMBSA-N

> <FORMULA>
C24H37NO2

> <MOLECULAR_WEIGHT>
371.5561

> <EXACT_MASS>
371.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
44.14247117027844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.17

> <JCHEM_LOGP>
5.479096267666667

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.412357019959163

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.448971538182775

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48192683597059827

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
124.40039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-04 g/l

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

> <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       9.576 -19.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.909 -20.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.243 -19.431   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.577 -19.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.910 -20.201   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.244 -19.431   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.578 -19.431   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.912 -20.201   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.245 -19.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.579 -19.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.913 -20.201   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.246 -19.431   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.580 -19.431   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.914 -20.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.247 -19.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.581 -19.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.915 -20.201   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.248 -19.431   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.582 -19.431   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.916 -20.201   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.250 -19.431   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.583 -20.201   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      38.917 -19.431   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      37.583 -21.741   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      40.251 -20.201   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      41.584 -19.431   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      42.918 -20.201   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
Anandamide (22:6, N-3)	ChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoyl ethanolamine	ChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-ethanolamine	ChEBI
N-cis-4,7,10,13,16,19-Docosahexanoylethanolamine	ChEBI
DHEA	HMDB
N-Docosahexaenoylethanolamine	MeSH
Synaptamide	MeSH

Chemical Formula

C₂₄H₃₇NO₂

Average Mass

371.5561 Da

Monoisotopic Mass

371.28243 Da

IUPAC Name

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

Traditional Name

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

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)NCCO

InChI Identifier

InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

GEEHOLRSGZPBSM-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 n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:85252 )
N-(long-chain-acyl)ethanolamine (CHEBI:85252 )
endocannabinoid (CHEBI:85252 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040009 )

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	6.17	ALOGPS
logP	5.48	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	-0.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	124.4 m³·mol⁻¹	ChemAxon
Polarizability	44.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013658

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029628

KNApSAcK ID

Not Available

Chemspider ID

4446571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283451

PDB ID

Not Available

ChEBI ID

85252

Good Scents ID

Not Available

References

General References

Showing NP-Card for Docosahexaenoyl Ethanolamide (NP0339391)

MOL for NP0339391 (Docosahexaenoyl Ethanolamide)

3D MOL for NP0339391 (Docosahexaenoyl Ethanolamide)

3D SDF for NP0339391 (Docosahexaenoyl Ethanolamide)

3D-SDF for NP0339391 (Docosahexaenoyl Ethanolamide)

PDB for NP0339391 (Docosahexaenoyl Ethanolamide)

3D PDB for NP0339391 (Docosahexaenoyl Ethanolamide)

SMILES for NP0339391 (Docosahexaenoyl Ethanolamide)

INCHI for NP0339391 (Docosahexaenoyl Ethanolamide)

Structure for NP0339391 (Docosahexaenoyl Ethanolamide)

3D Structure for NP0339391 (Docosahexaenoyl Ethanolamide)