NP-MRD: Showing NP-Card for Palmitoleoyl ethanolamide (NP0339381)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 21:33:01 UTC

Updated at

2024-09-11 21:33:01 UTC

NP-MRD ID

NP0339381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Palmitoleoyl ethanolamide

Description

Palmitoleoyl Ethanolamide, also known as POEA or palmitoleoyl-ea, 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, palmitoleoyl ethanolamide is considered to be a fatty amide lipid molecule. Palmitoleoyl Ethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303262018272D          

 21 20  0  0  0  0            999 V2000
10014.478110016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.193510016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.762710016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.906710016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.049510016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.622010016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.334210016.4058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10013.049510017.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.336410016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.620810016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.050810016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.905610016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.765410016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.188110016.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.590610016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.305110016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.019610016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.734510016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.448810016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.163410016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.880010016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  8  2  0  0  0  0
  6  9  1  0  0  0  0
  7 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  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339381

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-

> <INCHI_KEY>
WFRLANWAASSSFV-FPLPWBNLSA-N

> <FORMULA>
C18H35NO2

> <MOLECULAR_WEIGHT>
297.476

> <EXACT_MASS>
297.266779369

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.493366616866986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
4.621292561

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.47384261938588

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.469626555316175

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3086129187290516

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
91.2114

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoleoyl-EA

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0    8693.6928698.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8695.0288697.291   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8692.3578697.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8696.3598698.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8691.0268698.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8697.6948697.291   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8689.6908697.291   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8691.0268699.599   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8699.0288698.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.3598698.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8700.3628697.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8687.0248697.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8701.6958698.060   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8685.6858698.060   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8703.2368698.060   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8704.5698697.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8705.9038698.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8707.2388697.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8708.5718698.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8709.9058697.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8711.2438698.060   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    5                                                            
CONECT    9    6   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(Z)-Hexadec-9-enoyl ethanolamide	ChEBI
N-(2-Hydroxyethyl)palmitoleylamide	ChEBI
N-(9Z-Hexadecenoyl) ethanolamine	ChEBI
N-(9Z-Hexadecenoyl)-ethanolamine	ChEBI
Palmitoleoyl-ea	ChEBI
POEA	ChEBI
N-(9Z-Hexadecenoyl)-ethanolamide	HMDB
Palmitoleoyl-ethanolamide	HMDB
Palmitoleoyl-ethanolamine	HMDB
Polyoxyethyleneamine	HMDB
(9Z)-N-(2-Hydroxyethyl)-9-hexadecenamide	HMDB
Palmitoleoyl ethanolamide	HMDB

Chemical Formula

C₁₈H₃₅NO₂

Average Mass

297.4760 Da

Monoisotopic Mass

297.26678 Da

IUPAC Name

(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide

Traditional Name

palmitoleoyl-EA

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-

InChI Key

WFRLANWAASSSFV-FPLPWBNLSA-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-(monounsaturated fatty acyl)ethanolamine (CHEBI:71465 )
N-(long-chain-acyl)ethanolamine (CHEBI:71465 )
endocannabinoid (CHEBI:71465 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040043 )

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	6.07	ALOGPS
logP	4.62	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.47	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	15	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	38.49 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

HMDB0013648

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029618

KNApSAcK ID

Not Available

Chemspider ID

8011589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9835868

PDB ID

Not Available

ChEBI ID

71465

Good Scents ID

Not Available

References

General References

Showing NP-Card for Palmitoleoyl ethanolamide (NP0339381)

MOL for NP0339381 (Palmitoleoyl ethanolamide)

3D MOL for NP0339381 (Palmitoleoyl ethanolamide)

3D SDF for NP0339381 (Palmitoleoyl ethanolamide)

3D-SDF for NP0339381 (Palmitoleoyl ethanolamide)

PDB for NP0339381 (Palmitoleoyl ethanolamide)

3D PDB for NP0339381 (Palmitoleoyl ethanolamide)

SMILES for NP0339381 (Palmitoleoyl ethanolamide)

INCHI for NP0339381 (Palmitoleoyl ethanolamide)

Structure for NP0339381 (Palmitoleoyl ethanolamide)

3D Structure for NP0339381 (Palmitoleoyl ethanolamide)