General Information of the Compound
Compound ID
CP0055947
Compound Name
(15S)-prostaglandin E2
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Synonyms
(15S)-Prostaglandin E2
(5Z,11-alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
(5Z,11.alpha.,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
(5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
(5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
(E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid
(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-(8CI)
7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
Alpha, PGE2
Alpha, Prostaglandin E2
BML1-F07
BMS-279654 & PGE2
Cervidil
Cervidil (TN)
Dinoproston
Dinoprostona
Dinoprostona [INN-Spanish]
Dinoprostone
Dinoprostone (JAN/USP/INN)
Dinoprostone Prostaglandin E2
Dinoprostone [USAN:INN:BAN:JAN]
Dinoprostone beta-Cyclodextrin Clathrate
Dinoprostonum
Dinoprostonum [INN-Latin]
E2 alpha, Prostaglandin
E2, Prostaglandin
E2alpha, Prostaglandin
Gel, Prepidil
L-7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
L-PGE2
L-Prostaglandin E2
Minprositin E2
Minprostin E2
PGE2
PGE2 alpha
PGE2alpha
Prepidil
Prepidil (TN)
Prepidil Gel
Propess
Propess (TN)
Prostaglandin E2
Prostaglandin E2 alpha
Prostaglandin E2alpha
Prostarmon E2
Prostarmon E;Prostin E
Prostenon
Prostin
Prostin E2
Prostin E2 (TN)
U 12062
U-12062
[3H]PGE2
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Structure
Formula
C20H32O5
Molecular Weight
352.471
Canonical SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
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InChI
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
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InChIKey
XEYBRNLFEZDVAW-ARSRFYASSA-N
CAS
363-24-6
Physicochemical Property
logP
3.2511
Rotatable Bonds
12
Heavy Atom Count
25
Polar Areas
94.83
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
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: 5280360
SID: 99431525
ChEMBL ID
CHEMBL548
DrugBank ID
DB00917
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: PT02279, Prostacyclin receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 347 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 260 nM
2 Ki > 10000 nM
Protein ID: PT01205, Prostaglandin E2 receptor EP1 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 3.7 nM
   TI
   LI
   LO
   TS
CL000064 Chem-1 Rattus norvegicus (Rat)  1
1
IC50 < 30 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 9.1 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 1.1 nM
2 Ki = 9.1 nM
3 Ki = 18 nM
Protein ID: PT02988, Prostaglandin E2 receptor EP1 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 6 nM
   TI
   LI
   LO
   TS
Protein ID: PT05828, Prostaglandin E2 receptor EP2 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
EC50 = 0.2 nM
   TI
   LI
   LO
   TS
2
IC50 = 5.2 nM
   TI
   LI
   LO
   TS
Protein ID: PT00948, Prostaglandin E2 receptor EP2 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 1.9 nM
   TI
   LI
   LO
   TS
CL000314 HEK293T/17 Homo sapiens (Human)  2
1
EC50 = 9.3 nM
   TI
   LI
   LO
   TS
2
EC50 = 331 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  5
1
EC50 = 346 nM
   TI
   LI
   LO
   TS
2
IC50 = 2.6 nM
   TI
   LI
   LO
   TS
3
IC50 = 4 nM
   TI
   LI
   LO
   TS
4
Ki = 1.03 nM
   TI
   LI
   LO
   TS
5
Ki = 4.9 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 2.1 nM
2 IC50 = 2.2 nM
3 IC50 = 3.3 nM
4 IC50 = 37.7 nM
5 Ki = 1.7 nM
6 Ki = 4.9 nM
7 Ki = 38 nM
Protein ID: PT02989, Prostaglandin E2 receptor EP2 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 22 nM
   TI
   LI
   LO
   TS
Protein ID: PT01367, Prostaglandin E2 receptor EP3 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 2.5 nM
   TI
   LI
   LO
   TS
CL000064 Chem-1 Rattus norvegicus (Rat)  1
1
IC50 < 3 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  2
1
Ki = 0.33 nM
   TI
   LI
   LO
   TS
2
Ki = 2.17 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 0.94 nM
2 Ki = 0.33 nM
3 Ki = 5 nM
Protein ID: PT02345, Prostaglandin E2 receptor EP3 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 5 nM
   TI
   LI
   LO
   TS
Protein ID: PT01534, Prostaglandin E2 receptor EP4 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000314 HEK293T/17 Homo sapiens (Human)  2
1
EC50 = 0.02 nM
   TI
   LI
   LO
   TS
2
EC50 = 0.583 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  4
1
EC50 = 3 nM
   TI
   LI
   LO
   TS
2
IC50 = 0.55 nM
   TI
   LI
   LO
   TS
3
Ki = 0.11 nM
   TI
   LI
   LO
   TS
4
Ki = 0.79 nM
   TI
   LI
   LO
   TS
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 7.5 nM
   TI
   LI
   LO
   TS
CL000065 HEK293-EBNA Homo sapiens (Human)  1
1
IC50 = 0.7 nM
   TI
   LI
   LO
   TS
CL000064 Chem-1 Rattus norvegicus (Rat)  3
1
IC50 = 1.1 nM
   TI
   LI
   LO
   TS
2
IC50 = 5 nM
   TI
   LI
   LO
   TS
3
Ki = 0.45 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 0.45 nM
2 IC50 = 3.8 nM
3 IC50 = 9.9 nM
4 Ki = 0.17 nM
5 Ki = 0.79 nM
6 Ki = 1.9 nM
7 Ki = 3.1 nM
Protein ID: PT04548, Prostaglandin E2 receptor EP4 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
EC50 = 0.7 nM
   TI
   LI
   LO
   TS
2
IC50 = 2.1 nM
   TI
   LI
   LO
   TS
Protein ID: PT02346, Prostaglandin E2 receptor EP4 subtype
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 3.1 nM
   TI
   LI
   LO
   TS
Protein ID: PT01823, Prostaglandin F2-alpha receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000064 Chem-1 Rattus norvegicus (Rat)  1
1
EC50 = 250 nM
   TI
   LI
   LO
   TS
Protein ID: PT06206, Solute carrier family 22 member 7
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000009 LLC-PK1 Sus scrofa (Pig)  1
1
Km = 38500 nM
   TI
   LI
   LO
   TS
Protein ID: PT06205, Solute carrier organic anion transporter family member 2A1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000017 HeLa Homo sapiens (Human)  1
1
Km = 94 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Dinoprostone )
Drug Name Dinoprostone
Company Pfizer Pharmaceuticals
Indication
Medical abortion
Approved
Target(s)
Prostaglandin F2-alpha receptor (PTGFR)
Antagonist
Prostaglandin E2 receptor EP2 (PTGER2)
Antagonist