Showing NP-Card for alpha-Linolenoyl ethanolamide (NP0339368)

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Record Information
Version2.0
Created at2024-09-11 21:29:23 UTC
Updated at2024-09-11 21:29:23 UTC
NP-MRD IDNP0339368
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Linolenoyl ethanolamide
DescriptionAlpha-Linolenoyl ethanolamide, also known as alpha-lea or alea compound, 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, Alpha-linolenoyl ethanolamide is considered to be a fatty amide lipid molecule. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). Alpha-Linolenoyl ethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. 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. Alpha-Linolenoyl ethanolamide is a N-acylethanolamine.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339368 (alpha-Linolenoyl ethanolamide)

  Mrv0541 02271200282D          

 23 22  0  0  0  0            999 V2000
    5.3431  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2009  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9155  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3444  -15.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0589  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7734  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4878  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2023  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9168  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6313  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3458  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0602  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7747  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -14.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2036  -15.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9181  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6326  -15.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3471  -15.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
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 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
M  END
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3D MOL for NP0339368 (alpha-Linolenoyl ethanolamide)

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3D SDF for NP0339368 (alpha-Linolenoyl ethanolamide)
  Mrv0541 02271200282D          

 23 22  0  0  0  0            999 V2000
    5.3431  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2009  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9155  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3444  -15.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0589  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7734  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4878  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2023  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9168  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6313  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3458  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0602  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7747  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -14.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2036  -15.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9181  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6326  -15.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3471  -15.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-

> <INCHI_KEY>
HBJXRRXWHSHZPU-PDBXOOCHSA-N

> <FORMULA>
C20H35NO2

> <MOLECULAR_WEIGHT>
321.4974

> <EXACT_MASS>
321.266779369

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.153610668212025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
4.786586577666667

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.473842619386154

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.469626555316182

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3259293690079673

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
102.64659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339368 (alpha-Linolenoyl ethanolamide)
Download
PDB for NP0339368 (alpha-Linolenoyl 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       9.974 -28.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.307 -29.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.641 -28.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.975 -28.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.308 -29.039   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.642 -28.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.976 -28.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.310 -29.039   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.643 -28.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.977 -28.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.311 -29.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.644 -28.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.978 -29.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.312 -28.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.645 -29.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.979 -28.269   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.313 -29.039   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.647 -28.269   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      32.647 -26.729   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      33.980 -29.039   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      35.314 -28.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.648 -29.039   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      37.981 -28.269   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0339368 (alpha-Linolenoyl ethanolamide)
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SMILES for NP0339368 (alpha-Linolenoyl ethanolamide)
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO
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INCHI for NP0339368 (alpha-Linolenoyl ethanolamide)
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-
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View in JSmol
Synonyms
ValueSource
a-Linolenoyl ethanolamideGenerator
Α-linolenoyl ethanolamideGenerator
Linoleoyl ethanolamideHMDB
alpha-LEAHMDB
N-cis-9,12,15-OctadecatrienoylethanolamineHMDB
ALEA compoundHMDB
alpha-Linolenoyl ethanolamideMeSH
Chemical FormulaC20H35NO2
Average Mass321.4974 Da
Monoisotopic Mass321.26678 Da
IUPAC Name(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide
Traditional Name(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-
InChI KeyHBJXRRXWHSHZPU-PDBXOOCHSA-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 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.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct ParentN-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 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
logP5.6ALOGPS
logP4.79ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.65 m³·mol⁻¹ChemAxon
Polarizability40.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013624  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029601  
KNApSAcK IDNot Available
Chemspider ID4446569  
KEGG Compound IDC13828  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283449  
PDB IDNot Available
ChEBI ID613508  
Good Scents IDNot Available
References
General References