NP-MRD: Showing NP-Card for Dihomo-gamma-Linolenoyl ethanolamide (NP0339369)

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Record Information

Version

2.0

Created at

2024-09-11 21:29:42 UTC

Updated at

2024-09-11 21:29:43 UTC

NP-MRD ID

NP0339369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihomo-gamma-Linolenoyl ethanolamide

Description

Dihomo-gamma-Linolenoyl ethanolamide, also known as N-(8Z,11Z,14Z-eicosatrienoyl)-ethanolamine or anandamide (20.3,N-6), 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, dihomo-gamma-linolenoyl ethanolamide is considered to be a fatty amide lipid molecule. Dihomo-gamma-Linolenoyl ethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 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). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1652309131700092D          
 
 25 24  0  0  0  0            999 V2000
   16.5214  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3459  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8067  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0605  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0922  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7751  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5996  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6629  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3142  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9484  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0288  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2338  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8533  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5192  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5679  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8046  -10.7343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5192   -9.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2826  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9971  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7117  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4263  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0906  -10.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3758  -10.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6616  -10.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  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
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

> <INCHI_KEY>
ULQWKETUACYZLI-QNEBEIHSSA-N

> <FORMULA>
C22H39NO2

> <MOLECULAR_WEIGHT>
349.5506

> <EXACT_MASS>
349.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.388786615786984

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
5.675723907666667

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.41312374672419

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.449852373793465

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3086129483201976

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
111.84859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hglea

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-17         0                                  
HETATM    1  C   UNK     0      30.840 -20.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.379 -20.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.506 -19.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.713 -19.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.172 -20.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.047 -20.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.838 -19.268   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.586 -20.037   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.504 -20.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.920 -19.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.170 -19.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.254 -20.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.836 -20.037   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.793 -20.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.502 -19.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.127 -19.268   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      20.169 -20.037   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      21.502 -17.729   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      43.461 -20.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.795 -19.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      46.129 -20.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      47.462 -19.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.836 -19.267   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.502 -20.037   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.168 -19.267   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15   23                                                       
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17   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
8,11,14-Eicosatrienoylethanolamide	ChEBI
Anandamide (20.3,N-6)	ChEBI
HGLEA	ChEBI
Homo-gamma-linolenylethanolamide	ChEBI
N-(8Z,11Z,14Z-Eicosatrienoyl)-ethanolamine	ChEBI
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	ChEBI
Homo-g-linolenylethanolamide	Generator
Homo-γ-linolenylethanolamide	Generator
Dihomo-g-linolenoyl ethanolamide	Generator
Dihomo-γ-linolenoyl ethanolamide	Generator
(8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-8,11,14-trienamide	HMDB
DGLA ea	HMDB
Dihomo-gamma-linolenoylethanol amide	HMDB
Homo-gamma-linolenoyl ethanolamide	HMDB
Dihomo-g-linolenoyl-ea	Generator
Dihomo-γ-linolenoyl-ea	Generator

Chemical Formula

C₂₂H₃₉NO₂

Average Mass

349.5506 Da

Monoisotopic Mass

349.29808 Da

IUPAC Name

(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

Traditional Name

hglea

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

InChI Key

ULQWKETUACYZLI-QNEBEIHSSA-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:34488 )
N-(long-chain-acyl)ethanolamine (CHEBI:34488 )
N-acyl ethanolamides (endocannabinoids) (C13828 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040011 )

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	6.28	ALOGPS
logP	5.68	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	-1.3	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	17	ChemAxon
Refractivity	111.85 m³·mol⁻¹	ChemAxon
Polarizability	44.39 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

HMDB0013625

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029602

KNApSAcK ID

Not Available

Chemspider ID

4445443

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282272

PDB ID

Not Available

ChEBI ID

34488

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dihomo-gamma-Linolenoyl ethanolamide (NP0339369)

MOL for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

3D MOL for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

3D SDF for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

3D-SDF for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

PDB for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

3D PDB for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

SMILES for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

INCHI for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

Structure for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)

3D Structure for NP0339369 (Dihomo-gamma-Linolenoyl ethanolamide)