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

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Record Information

Version

2.0

Created at

2024-09-11 21:29:23 UTC

Updated at

2024-09-11 21:29:23 UTC

NP-MRD ID

NP0339368

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Linolenoyl ethanolamide

Description

Alpha-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

MOL SDF PDB SMILES InChI


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
a-Linolenoyl ethanolamide	Generator
Α-linolenoyl ethanolamide	Generator
Linoleoyl ethanolamide	HMDB
alpha-LEA	HMDB
N-cis-9,12,15-Octadecatrienoylethanolamine	HMDB
ALEA compound	HMDB
alpha-Linolenoyl ethanolamide	MeSH

Chemical Formula

C₂₀H₃₅NO₂

Average Mass

321.4974 Da

Monoisotopic Mass

321.26678 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 Number

Not 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 Key

HBJXRRXWHSHZPU-PDBXOOCHSA-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-acyl ethanolamines (endocannabinoids) (LMFA08040007 )

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	5.6	ALOGPS
logP	4.79	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	-0.33	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	15	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	40.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013624

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029601

KNApSAcK ID

Not Available

Chemspider ID

4446569

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283449

PDB ID

Not Available

ChEBI ID

613508

Good Scents ID

Not Available

References

General References

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

MOL for NP0339368 (alpha-Linolenoyl ethanolamide)

3D MOL for NP0339368 (alpha-Linolenoyl ethanolamide)

3D SDF for NP0339368 (alpha-Linolenoyl ethanolamide)

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

PDB for NP0339368 (alpha-Linolenoyl ethanolamide)

3D PDB for NP0339368 (alpha-Linolenoyl ethanolamide)

SMILES for NP0339368 (alpha-Linolenoyl ethanolamide)

INCHI for NP0339368 (alpha-Linolenoyl ethanolamide)

Structure for NP0339368 (alpha-Linolenoyl ethanolamide)

3D Structure for NP0339368 (alpha-Linolenoyl ethanolamide)