NP-MRD: Showing NP-Card for (5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid (NP0271747)

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Record Information

Version

2.0

Created at

2022-09-08 18:08:24 UTC

Updated at

2022-09-08 18:08:24 UTC

NP-MRD ID

NP0271747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid

Description

Anandamide, also known as AEA, 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, anandamide is considered to be a fatty amide lipid molecule. Anandamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid is found in Homo sapiens. (5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid was first documented in 1996 (PMID: 8814296). An N-(polyunsaturated fatty acyl)ethanolamine resulting from the formal condensation of carboxy group of arachidonic acid with amino group of ethanolamine (PMID: 15047233) (PMID: 15797258) (PMID: 15997233).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303262018252D          

 25 24  0  0  0  0            999 V2000
 9995.8523 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5668 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1377 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2816 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4231 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1067 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7084 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.423110000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8213 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9938 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5381 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2792 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3636 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5646 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0769 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7923 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6170 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3324 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0477 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8724 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5857 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.3011 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.0165 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.7299 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.4453 9999.3866    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  2  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  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  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>
NP0271747

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
LGEQQWMQCRIYKG-DOFZRALJSA-N

> <FORMULA>
C22H37NO2

> <MOLECULAR_WEIGHT>
347.5347

> <EXACT_MASS>
347.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.92950925412751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.98

> <JCHEM_LOGP>
5.313802251

> <ALOGPS_LOGS>
-5.87

> <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>
-1.3152897074754692

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
112.96520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anandamide

> <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    8658.9248666.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.2588665.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8657.5908665.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.5928666.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8656.2568666.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.1338666.291   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8654.9228665.522   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8656.2568667.830   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8664.4668665.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8653.5888666.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.8048666.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8652.2558665.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3458666.291   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8650.9218666.291   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8668.6778665.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.0128666.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.5528666.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.8878665.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8674.2228666.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.7628666.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8677.0938665.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8678.4298666.291   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8679.7648665.522   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8681.0968666.291   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8682.4318665.522   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   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChEBI
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChEBI
AEA	ChEBI
Anandamide (20.4, N-6)	ChEBI
Anandamide(20:4, N-6)	ChEBI
Arachidonic acid N-(hydroxyethyl)amide	ChEBI
Arachidonoyl ethanolamide	ChEBI
Arachidonylethanolamide	ChEBI
N-(2-Hydroxyethyl)anachidonamide	ChEBI
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine	ChEBI
N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamide	ChEBI
N-Arachidonoyl ethanolamine	ChEBI
N-Arachidonoyl-2-hydroxyethylamide	ChEBI
N-Arachidonoylethanolamine	ChEBI
Arachidonate N-(hydroxyethyl)amide	Generator
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl) ethanolamine	HMDB
5,8,11,14-Eicosatetraenoylethanolamide	HMDB
N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)	HMDB
N-(2-Hydroxyethyl)arachidonamide	HMDB
Anandamide (20.4,N-6)	HMDB
Arachidonoylethanolamide	HMDB
N-Arachidonoylethanolamide	HMDB
Anandamide	MeSH
N-(2-Hydroxyethyl)arachidonylamide	HMDB
N-Arachidonylethanolamide	HMDB
N-Arachidonylethanolamine	HMDB

Chemical Formula

C₂₂H₃₇NO₂

Average Mass

347.5347 Da

Monoisotopic Mass

347.28243 Da

IUPAC Name

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

Traditional Name

anandamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

InChI Key

LGEQQWMQCRIYKG-DOFZRALJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	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

fatty amide (CHEBI:2700 )
N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:2700 )
N-(long-chain-acyl)ethanolamine (CHEBI:2700 )
endocannabinoid (CHEBI:2700 )
N-acyl ethanolamides (endocannabinoids) (C11695 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040001 )

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	5.98	ALOGPS
logP	5.31	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	15.44	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	16	ChemAxon
Refractivity	112.97 m³·mol⁻¹	ChemAxon
Polarizability	43.93 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

HMDB0004080

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023303

KNApSAcK ID

Not Available

Chemspider ID

4445241

KEGG Compound ID

C11695

BioCyc ID

CPD-7598

BiGG ID

Not Available

Wikipedia Link

Anandamide

METLIN ID

Not Available

PubChem Compound

5281969

PDB ID

Not Available

ChEBI ID

2700

Good Scents ID

Not Available

References

General References

Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM, Becker GW: Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 1996 Sep 16;393(2-3):231-5. doi: 10.1016/0014-5793(96)00891-5. [PubMed:8814296 ]
Contassot E, Tenan M, Schnuriger V, Pelte MF, Dietrich PY: Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Gynecol Oncol. 2004 Apr;93(1):182-8. doi: 10.1016/j.ygyno.2003.12.040. [PubMed:15047233 ]
Chen P, Hu S, Yao J, Moore SA, Spector AA, Fang X: Induction of cyclooxygenase-2 by anandamide in cerebral microvascular endothelium. Microvasc Res. 2005 Jan;69(1-2):28-35. doi: 10.1016/j.mvr.2005.02.001. [PubMed:15797258 ]
Movahed P, Evilevitch V, Andersson TL, Jonsson BA, Wollmer P, Zygmunt PM, Hogestatt ED: Vascular effects of anandamide and N-acylvanillylamines in the human forearm and skin microcirculation. Br J Pharmacol. 2005 Sep;146(2):171-9. doi: 10.1038/sj.bjp.0706313. [PubMed:15997233 ]
LOTUS database [Link]

Showing NP-Card for (5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid (NP0271747)

MOL for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

3D MOL for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

3D SDF for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

3D-SDF for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

PDB for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

3D PDB for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

SMILES for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

INCHI for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

Structure for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)

3D Structure for NP0271747 ((5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid)