NP-MRD: Showing NP-Card for (9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid (NP0141505)

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Record Information

Version

2.0

Created at

2022-09-01 19:50:45 UTC

Updated at

2022-09-01 19:50:46 UTC

NP-MRD ID

NP0141505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid

Description

N-Oleoylethanolamine, also known as OEA or oleoyl monoethanolamide, 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, N-oleoylethanolamine is considered to be a fatty amide lipid molecule. (9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid is found in Apis cerana. (9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid was first documented in 2002 (PMID: 12056855). N-Oleoylethanolamine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12560208) (PMID: 12692337) (PMID: 11997249) (PMID: 17449181) (PMID: 18704536) (PMID: 19521349).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 62 61  0  0  0  0  0  0  0  0999 V2000
   -9.1943    1.4564    1.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9375    2.2658    1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1445    1.5856    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8163    0.1978    0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0655   -0.5270   -0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    0.1725   -0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995   -0.5787   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039    0.1840   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957   -0.4896   -2.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871   -0.9318   -2.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -0.8191   -1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -0.0059   -1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    0.0294   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626    0.7931   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297    0.1997   -0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -1.2019   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0845   -1.4764    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323   -0.7659    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8936   -0.0460    0.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9783   -0.8398    2.3210 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1936   -0.1574    2.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3380   -0.5757    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4810    0.1527    2.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9590    0.5858    2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9495    2.0564    2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6552    1.1464    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3642    2.2633    2.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2312    3.2670    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887    2.1691    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7284    1.6609   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698   -0.3488    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1961    0.1656    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7057   -0.6316   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227   -1.5846   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355    0.3093    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253    1.1963   -1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153   -1.5962   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679   -0.6059   -2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023    0.4954   -1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0512    1.1534   -2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3089   -0.6314   -4.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951   -1.4361   -3.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377   -1.8643   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5573   -0.3735   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866    0.9829   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384   -0.5794   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9751   -1.0216    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210    0.5511    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4538    0.9164    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    1.8232   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1130    0.8609   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8498    0.2718   -1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737   -1.8465   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439   -1.5930   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2703   -1.1881    1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2683   -2.5540    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5196   -1.4331    3.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4403   -0.3118    3.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0963    0.9578    2.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167   -0.4116    0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5789   -1.6525    1.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1150    0.2091    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
M  END


  Mrv1652311251922492D          

 23 22  0  0  0  0            999 V2000
10004.688010007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.403410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.118810007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.832010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.547410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.261710007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.976310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.801410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.516010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.230410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.945010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.659710007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.374310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.088710007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.805310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.520110007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.974810007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.259410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.546110007.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.830810007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.113410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.400110007.7791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.259410008.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  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
M  END
> <DATABASE_ID>
NP0141505

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

> <INCHI_KEY>
BOWVQLFMWHZBEF-KTKRTIGZSA-N

> <FORMULA>
C20H39NO2

> <MOLECULAR_WEIGHT>
325.5292

> <EXACT_MASS>
325.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.772357373818814

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.74

> <JCHEM_LOGP>
5.510429891

> <ALOGPS_LOGS>
-6.13

> <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>
-1.3086129187290512

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
100.41339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleoylethanolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-NOV-19         0                                  
HETATM    1  C   UNK     0    8675.4188681.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8676.7538680.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8678.0888681.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8679.4208680.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8680.7558681.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8682.0888680.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8683.4228681.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8684.9638681.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8686.2968680.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8687.6308681.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.9648680.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8690.2988681.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.6328680.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8692.9668681.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8694.3038680.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8695.6378681.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8674.0868680.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.7518681.188   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8671.4198680.418   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8670.0848681.188   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.7458680.418   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8667.4148681.188   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8672.7518682.726   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
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                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
N-(2-Hydroxyethyl)-9-octadecenamide	ChEBI
N-(2-Hydroxyethyl)oleamide	ChEBI
N-(9Z-Octadecenoyl) ethanolamine	ChEBI
N-(9Z-Octadecenoyl)-ethanolamine	ChEBI
N-(cis-9-Octadecenoyl) ethanolamine	ChEBI
N-(Hydroxyethyl)oleamide	ChEBI
N-Oleoyl ethanolamine	ChEBI
OEA	ChEBI
Oleamide mea	ChEBI
Oleoyl 1-ethanolamide	ChEBI
Oleoyl monoethanolamide	ChEBI
Oleoylethanolamide	ChEBI
N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide	HMDB
N-Oleoyl-2-aminoethanol	HMDB
NOE	HMDB
Oleic acid ethanolamide	HMDB
Oleic acid monoethanolamide	HMDB
N-OEA	HMDB
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamide	HMDB
N-(2-Hydroxyethyl)-9-Z-octadecenamide	HMDB
N-Oleoylethanolamide	HMDB
Oleoyl ethanolamide	HMDB
Oleoylethanolamine	HMDB
N-Oleoylethanolamine	ChEBI

Chemical Formula

C₂₀H₃₉NO₂

Average Mass

325.5292 Da

Monoisotopic Mass

325.29808 Da

IUPAC Name

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

Traditional Name

oleoylethanolamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

InChI Key

BOWVQLFMWHZBEF-KTKRTIGZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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:71466 )
N-(long-chain-acyl)ethanolamine (CHEBI:71466 )
endocannabinoid (CHEBI:71466 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040015 )

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	6.74	ALOGPS
logP	5.51	ChemAxon
logS	-6.1	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	17	ChemAxon
Refractivity	100.41 m³·mol⁻¹	ChemAxon
Polarizability	42.77 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

HMDB0002088

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022839

KNApSAcK ID

Not Available

Chemspider ID

4446574

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleoylethanolamide

METLIN ID

Not Available

PubChem Compound

5283454

PDB ID

Not Available

ChEBI ID

71466

Good Scents ID

Not Available

References

General References

Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. doi: 10.1152/ajpheart.00888.2002. Epub 2003 Jan 30. [PubMed:12560208 ]
Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. doi: 10.1104/pp.102.014936. [PubMed:12692337 ]
Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. doi: 10.1006/jmcc.2002.1533. [PubMed:12056855 ]
Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. doi: 10.1152/ajpcell.00471.2001. [PubMed:11997249 ]
Suardiaz M, Estivill-Torrus G, Goicoechea C, Bilbao A, Rodriguez de Fonseca F: Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. Pain. 2007 Dec 15;133(1-3):99-110. doi: 10.1016/j.pain.2007.03.008. Epub 2007 Apr 20. [PubMed:17449181 ]
Thabuis C, Tissot-Favre D, Bezelgues JB, Martin JC, Cruz-Hernandez C, Dionisi F, Destaillats F: Biological functions and metabolism of oleoylethanolamide. Lipids. 2008 Oct;43(10):887-94. doi: 10.1007/s11745-008-3217-y. Epub 2008 Aug 13. [PubMed:18704536 ]
Izzo AA, Piscitelli F, Capasso R, Marini P, Cristino L, Petrosino S, Di Marzo V: Basal and fasting/refeeding-regulated tissue levels of endogenous PPAR-alpha ligands in Zucker rats. Obesity (Silver Spring). 2010 Jan;18(1):55-62. doi: 10.1038/oby.2009.186. Epub 2009 Jun 11. [PubMed:19521349 ]
Ueda N, Tsuboi K, Uyama T: N-acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA). Prog Lipid Res. 2010 Oct;49(4):299-315. doi: 10.1016/j.plipres.2010.02.003. Epub 2010 Feb 10. [PubMed:20152858 ]
Fonseca BM, Correia-da-Silva G, Taylor AH, Lam PM, Marczylo TH, Konje JC, Bell SC, Teixeira NA: N-acylethanolamine levels and expression of their metabolizing enzymes during pregnancy. Endocrinology. 2010 Aug;151(8):3965-74. doi: 10.1210/en.2009-1424. Epub 2010 Jun 9. [PubMed:20534733 ]
LOTUS database [Link]

Showing NP-Card for (9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid (NP0141505)

MOL for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

3D MOL for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

3D SDF for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

3D-SDF for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

PDB for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

3D PDB for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

SMILES for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

INCHI for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

Structure for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)

3D Structure for NP0141505 ((9z)-n-(2-hydroxyethyl)octadec-9-enimidic acid)