General Information of the Compound
Compound ID
CP0035557
Compound Name
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
    Show/Hide
Synonyms
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
111-58-0
1HI5J9N8E6
CHEBI:71466
CHEMBL280065
EINECS 203-884-8
MLS002153155
Monoethanolamine oleic acid amide
N-(2-Hydroxyethyl)-9-octadecenamide
N-(2-Hydroxyethyl)oleamide
N-(9Z-octadecenoyl)-ethanolamine
N-(Hydroxyethyl)oleamide
N-oleoyl ethanolamine
N-oleoylethanolamide
N-oleoylethanolamine
NOE
OEA
OLEOYLETHANOLAMIDE
Oleamide MEA
Oleic acid ethanolamide
Oleoyl Ethanolamide
Oleoyl monoethanolamide
Oleylethanolamide
UNII-1HI5J9N8E6
n-Oleoylethanolamine
n-oleoylethanolamine
oleoylethanolamide
oleylethanolamide
    Show/Hide
Structure
Formula
C20H39NO2
Molecular Weight
325.537
Canonical SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
    Show/Hide
InChI
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-
    Show/Hide
InChIKey
BOWVQLFMWHZBEF-KTKRTIGZSA-N
CAS
111-58-0
Physicochemical Property
logP
5.1324
Rotatable Bonds
17
Heavy Atom Count
23
Polar Areas
49.33
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Complexity
23

"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).

    Show/Hide
Click to Show/Hide the External Link(s) of This Compound
PubChem ID
CID: 5283454
SID: 14801663
ChEMBL ID
CHEMBL280065
DrugBank ID
DB16495
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: PT01298, Cannabinoid receptor 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 1100 nM
   TI
   LI
   LO
   TS
CL000880 COS Chlorocebus aethiops (Green monkey)  1
1
Ki = 1100 nM
   TI
   LI
   LO
   TS
Protein ID: PT00834, Cannabinoid receptor 2
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki > 10000 nM
   TI
   LI
   LO
   TS
CL000880 COS Chlorocebus aethiops (Green monkey)  1
1
Ki > 10000 nM
   TI
   LI
   LO
   TS
Protein ID: PT06109, Geminin
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000015 SW480 Homo sapiens (Human)  1
1
Potency ~ 35481.3 nM
   TI
   LI
   LO
   TS
Protein ID: PT02455, Glucose-dependent insulinotropic receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
EC50 = 2200 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 930 nM
2 EC50 = 3200 nM
Protein ID: PT00910, Peroxisome proliferator-activated receptor alpha
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000017 HeLa Homo sapiens (Human)  1
1
EC50 = 120 nM
   TI
   LI
   LO
   TS
CL000083 MCF-7 Homo sapiens (Human)  2
1
EC50 = 152 nM
   TI
   LI
   LO
   TS
2
EC50 = 185 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 110 nM
Protein ID: PT00909, Peroxisome proliferator-activated receptor delta
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000017 HeLa Homo sapiens (Human)  1
1
EC50 = 1100 nM
   TI
   LI
   LO
   TS
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 = 890 nM
   TI
   LI
   LO
   TS
2
EC50 = 3650 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 40 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 = 1800 nM
   TI
   LI
   LO
   TS
2
IC50 = 5400 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( N-oleoylethanolamide )
Drug Name N-oleoylethanolamide
Target(s)
Peroxisome proliferator-activated receptor alpha (PPARA)
Agonist
G-protein coupled receptor 55 (GPR55)
Agonist
Cannabinoid receptor 1 (CB1)
Inhibitor
Glucose-dependent insulinotropic receptor (GPR119)
Agonist