NP-MRD: Showing NP-Card for 20-HETE ethanolamide (NP0339372)

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Record Information

Version

2.0

Created at

2024-09-11 21:30:36 UTC

Updated at

2024-09-11 21:30:36 UTC

NP-MRD ID

NP0339372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-HETE ethanolamide

Description

20-HETE ethanolamide, also known as 20-hete-ea or 20-hete-ethanolamine, 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, 20-hete ethanolamide is considered to be a fatty amide lipid molecule. 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). N-Oleoylethanolamine is an inhibitor of the sphingolipid signalling pathway via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). 20-HETE ethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 20-HETE ethanolamide was first documented in 2007 (PMID: 17272674). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration (PMID: 21289075) (PMID: 27000802).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303291817582D          

 26 25  0  0  0  0            999 V2000
 9995.4803 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1949 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9094 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7347 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4493 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1638 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9891 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7035 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4208 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2456 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9610 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6743 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4990 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2144 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.9298 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.6431 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.3585 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.0739 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.7872 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7657 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0512 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3364 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6218 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9072 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1927 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.051210000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv1652303291817582D          

 26 25  0  0  0  0            999 V2000
 9995.4803 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1949 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9094 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7347 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4493 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1638 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9891 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7035 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4208 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2456 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9610 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6743 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4990 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2144 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.9298 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.6431 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.3585 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.0739 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.7872 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7657 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0512 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3364 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6218 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9072 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1927 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.051210000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-

> <INCHI_KEY>
QRMZDMUHHZLRMH-DTLRTWKJSA-N

> <FORMULA>
C22H37NO3

> <MOLECULAR_WEIGHT>
363.5341

> <EXACT_MASS>
363.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.18547319965994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
3.877123634333334

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.375825066096787

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.435299736387627

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2323639576211178

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
114.89389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-hete-EA

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAR-18         0                                  
HETATM    1  C   UNK     0    8658.2308666.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.5648665.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.8988666.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.4388666.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.7728665.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.1068666.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.6468666.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.9808665.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.3198666.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.8588666.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.1948665.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.5258666.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8675.0658666.291   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.4008665.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.7368666.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8679.0678665.522   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8680.4038666.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8681.7388665.522   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8683.0698666.291   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8656.8968665.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8655.5628666.291   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8654.2288665.522   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0    8652.8948666.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8651.5608665.522   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8650.2268666.291   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8655.5628667.830   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
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                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
20-HETE-ea	ChEBI
20-HETE-ethanolamine	ChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoic acid ethanolamide	ChEBI
20-Hydroxy-5,8,11,14-icosatetraenoic acid ethanolamide	ChEBI
20-Hydroxyanandamide	ChEBI
20-Hydroxyarachidonic acid ethanolamide	ChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine	ChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-icosatetraenoyl)ethanolamine	ChEBI
N-[5Z,8Z,11Z,14Z-20-Hydroxyicosatetraenoyl]ethanolamine	ChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoate ethanolamide	Generator
20-Hydroxy-5,8,11,14-icosatetraenoate ethanolamide	Generator
20-Hydroxyarachidonate ethanolamide	Generator
20-HETE ea	HMDB
20-Hydroxy aea	HMDB
20-Hydroxy arachidonoyl ethanolamide	HMDB
20-Hydroxyepoxyeicosatrienoate	HMDB
20-Hydroxyepoxyeicosatrienoic acid	HMDB
20-Hydroxyepoxyeicosatrienoic acid ethanolamide	HMDB

Chemical Formula

C₂₂H₃₇NO₃

Average Mass

363.5341 Da

Monoisotopic Mass

363.27734 Da

IUPAC Name

(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

Traditional Name

20-hete-EA

CAS Registry Number

Not Available

SMILES

OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-

InChI Key

QRMZDMUHHZLRMH-DTLRTWKJSA-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) (LMFA08040039 )

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	4.88	ALOGPS
logP	3.88	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	15.44	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	114.89 m³·mol⁻¹	ChemAxon
Polarizability	44.19 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

HMDB0013630

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029607

KNApSAcK ID

Not Available

Chemspider ID

21467685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

35027640

PDB ID

Not Available

ChEBI ID

136992

Good Scents ID

Not Available

References

General References

Snider NT, Kornilov AM, Kent UM, Hollenberg PF: Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther. 2007 May;321(2):590-7. doi: 10.1124/jpet.107.119321. Epub 2007 Feb 1. [PubMed:17272674 ]
Sridar C, Snider NT, Hollenberg PF: Anandamide oxidation by wild-type and polymorphically expressed CYP2B6 and CYP2D6. Drug Metab Dispos. 2011 May;39(5):782-8. doi: 10.1124/dmd.110.036707. Epub 2011 Feb 2. [PubMed:21289075 ]
Walker VJ, Griffin AP, Hammar DK, Hollenberg PF: Metabolism of Anandamide by Human Cytochrome P450 2J2 in the Reconstituted System and Human Intestinal Microsomes. J Pharmacol Exp Ther. 2016 Jun;357(3):537-44. doi: 10.1124/jpet.116.232553. Epub 2016 Mar 21. [PubMed:27000802 ]

Showing NP-Card for 20-HETE ethanolamide (NP0339372)

MOL for NP0339372 (20-HETE ethanolamide)

3D MOL for NP0339372 (20-HETE ethanolamide)

3D SDF for NP0339372 (20-HETE ethanolamide)

3D-SDF for NP0339372 (20-HETE ethanolamide)

PDB for NP0339372 (20-HETE ethanolamide)

3D PDB for NP0339372 (20-HETE ethanolamide)

SMILES for NP0339372 (20-HETE ethanolamide)

INCHI for NP0339372 (20-HETE ethanolamide)

Structure for NP0339372 (20-HETE ethanolamide)

3D Structure for NP0339372 (20-HETE ethanolamide)