General Information of the Compound
Compound ID
CP0037555
Compound Name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
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Synonyms
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
5,8,11,14-Eicosatetraenoylethanolamide
94421-68-8
AEA
Anandamide
Anandamide (20.4, n-6)
Anandamide (20:4, n-6)
Anandamide(20:4, n-6)
Arachidonic acid N-(hydroxyethyl)amide
Arachidonoyl ethanolamide
Arachidonoyl-EA
Arachidonylethanolamide
N-(2-Hydroxyethyl)anachidonamide
N-Arachidonoyl-2-hydroxyethylamide
N-Arachidonoylethanolamine
N-arachidonoyl ethanolamine
UNII-UR5G69TJKH
arachidonoylethanolamide
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Structure
Formula
C22H37NO2
Molecular Weight
347.543
Canonical SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
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InChI
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-
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InChIKey
LGEQQWMQCRIYKG-DOFZRALJSA-N
CAS
94421-68-8
Physicochemical Property
logP
5.2406
Rotatable Bonds
16
Heavy Atom Count
25
Polar Areas
49.33
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Complexity
25

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 5281969
SID: 12014921
ChEMBL ID
CHEMBL15848
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT02190, Cannabinoid receptor 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
EC50 = 69 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 72 nM
2 Ki = 78 nM
Protein ID: PT01298, Cannabinoid receptor 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  3
1
Ki = 11 nM
   TI
   LI
   LO
   TS
2
Ki = 70 nM
   TI
   LI
   LO
   TS
3
Ki = 72 nM
   TI
   LI
   LO
   TS
CL000880 COS Chlorocebus aethiops (Green monkey)  2
1
Ki = 70 nM
   TI
   LI
   LO
   TS
2
Ki = 72 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 0.290035 nM
2 Ki = 39.2 nM
3 Ki = 50 nM
4 Ki = 72 nM
5 Ki = 89 nM
Protein ID: PT00834, Cannabinoid receptor 2
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
Ki = 160 nM
   TI
   LI
   LO
   TS
2
Ki = 168 nM
   TI
   LI
   LO
   TS
CL000880 COS Chlorocebus aethiops (Green monkey)  1
1
Ki = 180 nM
   TI
   LI
   LO
   TS
CL000065 HEK293-EBNA Homo sapiens (Human)  1
1
Ki > 1000 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 0.409933 nM
2 Ki = 180 nM
3 Ki = 371 nM
Protein ID: PT01998, Cannabinoid receptor 2
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki > 1000 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 1926 nM
Protein ID: PT01099, Fatty-acid amide hydrolase 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000100 U-937 Homo sapiens (Human)  1
1
Ki > 10000 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 3400 nM
2 IC50 = 4100 nM
Protein ID: PT02183, Transient receptor potential cation channel subfamily V member 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
EC50 = 200 nM
   TI
   LI
   LO
   TS
2
EC50 = 490 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 15.8 nM
Protein ID: PT06137, Transient receptor potential cation channel subfamily V member 2
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
IC50 = 960 nM
   TI
   LI
   LO
   TS
2
IC50 = 8600 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Anandamide )
Drug Name Anandamide
Target(s)
Cannabinoid receptor 1 (CB1)
Agonist