prostaglandin E(2) (CHEBI:15551)

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CHEBI:15551 - prostaglandin E₂

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ChEBI Name	prostaglandin E₂

ChEBI ID	CHEBI:15551

ChEBI ASCII Name	prostaglandin E2

Definition	Prostaglandin F_2α in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E₂ is the most common and most biologically potent of mammalian prostaglandins.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:26323, CHEBI:10910, CHEBI:10911, CHEBI:4625, CHEBI:114125, CHEBI:8512

Supplier Information	eMolecules:1935398, eMolecules:26753648, ZINC000008215926

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

P2E - Ideal conformer

Mrv1927 06092115523D

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Time for openFile(P2E - Ideal conformer

Mrv1927 06092115523D

57 57 0 0 0 0 999 V2000

3.9310 3.0420 0.0320 C 0 0 1 0 0 0 0 0 0 0 0 0

4.4680 1.6530 -0.3230 C 0 0 1 0 0 0 0 0 0 0 0 0

3.3120 0.7620 -0.7820 C 0 0 1 0 0 0 0 0 0 0 0 0

3.8410 -0.6060 -1.1310 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2990 -1.6730 -0.5990 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0440 -1.5490 0.2270 C 0 0 1 0 0 0 0 0 0 0 0 0

0.9780 -2.5000 -0.3200 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4100 -3.9370 -0.1110 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3970 -4.4610 -0.5690 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.3430 -2.3130 0.4550 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.9090 -3.7520 0.5700 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.7830 -3.8650 1.6950 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3720 -4.5960 0.7800 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.2900 -1.4320 -0.3170 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7130 -0.3080 0.2060 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6600 0.5740 -0.5660 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.0370 -0.0800 -1.7790 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.9080 0.8440 0.2770 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.8120 1.8380 -0.4540 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.0600 2.1090 0.3890 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.9640 3.1030 -0.3420 C 0 0 1 0 0 0 0 0 0 0 0 0

-8.2120 3.3730 0.5010 C 0 0 0 0 0 0 0 0 0 0 0 0

6.1940 3.4800 0.5190 O 0 0 0 0 0 0 0 0 0 0 0 0

5.0690 3.9190 0.4840 C 0 0 0 0 0 0 0 0 0 0 0 0

4.8340 5.1900 0.8480 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4580 3.4830 -0.8450 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1990 2.9540 0.8340 H 0 0 0 0 0 0 0 0 0 0 0 0

5.2000 1.7410 -1.1250 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9410 1.2120 0.5540 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5800 0.6740 0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8390 1.2030 -1.6590 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6660 -0.7060 -1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7510 -2.6420 -0.7520 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2640 -1.8060 1.2630 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6760 -0.5240 0.1770 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8180 -2.3100 -1.3810 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1510 -1.8970 1.4440 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4220 -4.0410 -0.3470 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1630 -4.7470 1.8100 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2040 -5.6270 0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6870 -4.5580 1.8230 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6200 -1.7260 -1.3030 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3830 -0.0130 1.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1680 1.5180 -0.8000 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4810 -0.9280 -1.6470 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.4480 -0.0890 0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6120 1.2620 1.2400 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2720 2.7720 -0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.1070 1.4210 -1.4170 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.6000 1.1750 0.5480 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7640 2.5260 1.3520 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.4240 4.0360 -0.5010 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.2590 2.6850 -1.3050 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.7520 2.4390 0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.9170 3.7900 1.4640 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.8560 4.0810 -0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0

5.5950 5.7140 1.1310 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 24 1 0 0 0 0

2 3 1 0 0 0 0

3 4 1 0 0 0 0

4 5 2 0 0 0 0

5 6 1 0 0 0 0

6 7 1 0 0 0 0

7 8 1 0 0 0 0

7 10 1 0 0 0 0

8 9 2 0 0 0 0

8 13 1 0 0 0 0

10 11 1 0 0 0 0

10 14 1 0 0 0 0

11 12 1 0 0 0 0

11 13 1 0 0 0 0

14 15 2 0 0 0 0

15 16 1 0 0 0 0

16 17 1 0 0 0 0

16 18 1 0 0 0 0

18 19 1 0 0 0 0

19 20 1 0 0 0 0

20 21 1 0 0 0 0

21 22 1 0 0 0 0

23 24 2 0 0 0 0

24 25 1 0 0 0 0

1 26 1 0 0 0 0

1 27 1 0 0 0 0

2 28 1 0 0 0 0

2 29 1 0 0 0 0

3 30 1 0 0 0 0

3 31 1 0 0 0 0

4 32 1 0 0 0 0

5 33 1 0 0 0 0

6 34 1 0 0 0 0

6 35 1 0 0 0 0

7 36 1 6 0 0 0

10 37 1 1 0 0 0

11 38 1 6 0 0 0

12 39 1 0 0 0 0

13 40 1 0 0 0 0

13 41 1 0 0 0 0

14 42 1 0 0 0 0

15 43 1 0 0 0 0

16 44 1 6 0 0 0

17 45 1 0 0 0 0

18 46 1 0 0 0 0

18 47 1 0 0 0 0

19 48 1 0 0 0 0

19 49 1 0 0 0 0

20 50 1 0 0 0 0

20 51 1 0 0 0 0

21 52 1 0 0 0 0

21 53 1 0 0 0 0

22 54 1 0 0 0 0

22 55 1 0 0 0 0

22 56 1 0 0 0 0

25 57 1 0 0 0 0

M END): 18 ms

reading 57 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

57 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin with various medical uses. Alprostadil and misoprostol are synthetic forms of prostaglandin E1 used as medications. Lubiprostone, a derivative of prostaglandin E1, is also used as a medication. Prostaglandin E1 is a vasodilator. It has various effects in the body that include opening blood vessels, relaxing smooth muscle, inhibiting clotting, and causing uterine contractions. In infants with certain congenital heart defects, alprostadil is delivered by slow injection into a vein to maintain a patent ductus arteriosus until surgery can be carried out. By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction. Common side effects when given to babies include decreased breathing, fever, and low blood pressure. When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism). Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981. Misoprostol has various obstetric uses. It is used to induce abortion, to completely empty the uterus after a miscarriage, to induce labor, and to prevent and treat postpartum hemorrhage. The medication is available through many routes. It can be swallowed, dissolved in the mouth, placed in the vagina, or placed in the rectum. Misoprostol can also be used to manage duodenal ulcers and peptic ulcer disease when other medications are not effective. It is on the World Health Organization's List of Essential Medicines for its obstetric uses. Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally. Common side effects include diarrhea, vomiting, and abdominal pain.
Read full article at Wikipedia

Formula

C20H32O5

Net Charge

Average Mass

352.471

Monoisotopic Mass

352.22497

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

InChIKey

XEYBRNLFEZDVAW-ARSRFYASSA-N

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	See: MetaboLights Study
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

Application(s):	oxytocic A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	prostaglandin E₂ (CHEBI:15551) has role human metabolite (CHEBI:77746) prostaglandin E₂ (CHEBI:15551) has role mouse metabolite (CHEBI:75771) prostaglandin E₂ (CHEBI:15551) has role oxytocic (CHEBI:36063) prostaglandin E₂ (CHEBI:15551) is a prostaglandins E (CHEBI:26338) prostaglandin E₂ (CHEBI:15551) is conjugate acid of prostaglandin E₂(1−) (CHEBI:606564)

Incoming	13,14-dihydro-15-oxo-prostaglandin E₂ (CHEBI:15550) has functional parent prostaglandin E₂ (CHEBI:15551) 15-dehydro-prostaglandin E₂ (CHEBI:15547) has functional parent prostaglandin E₂ (CHEBI:15551) 2-[(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl]-sn-glycero-3-phosphocholine (CHEBI:137585) has functional parent prostaglandin E₂ (CHEBI:15551) 2-[(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl]-sn-glycero-3-phosphoethanolamine (CHEBI:138361) has functional parent prostaglandin E₂ (CHEBI:15551) 20-hydroxyprostaglandin E₂ (CHEBI:137370) has functional parent prostaglandin E₂ (CHEBI:15551) 8-epi-prostaglandin E₂ (CHEBI:131888) has functional parent prostaglandin E₂ (CHEBI:15551) nitroproston (CHEBI:142127) has functional parent prostaglandin E₂ (CHEBI:15551) prostaglandin E₂ 1-glyceryl ester (CHEBI:90230) has functional parent prostaglandin E₂ (CHEBI:15551) prostaglandin E₂ 2-glyceryl ester (CHEBI:137172) has functional parent prostaglandin E₂ (CHEBI:15551) prostaglandin E₂(1−) (CHEBI:606564) is conjugate base of prostaglandin E₂ (CHEBI:15551)

IUPAC Name

(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid

INNs	Sources
dinoprostona	WHO MedNet
dinoprostone	WHO MedNet
dinoprostone	WHO MedNet
dinoprostonum	WHO MedNet

Synonyms	Sources
(15S)-prostaglandin E₂	ChemIDplus
(5Z,11α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid	ChemIDplus
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	KEGG COMPOUND
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate	KEGG COMPOUND
(E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid	ChemIDplus
(Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid	ChEMBL
Dinoproston	ChemIDplus
PGE₂	ChemIDplus
PGE2	KEGG COMPOUND
Prostaglandin E2	KEGG COMPOUND
U 12062	ChemIDplus
U-12,062	ChemIDplus
U-12062	ChemIDplus

Brand Names	Sources
Cervidil	KEGG DRUG
Cerviprime	ChemIDplus
Cerviprost	ChemIDplus
Enzaprost E	ChemIDplus
Glandin-E2	ChEBI
Minprositin E2	ChemIDplus
Minprostin E2	ChemIDplus
Prepidil	KEGG DRUG
Propess	DrugBank
Prostarmon E	ChemIDplus
Prostenone	ChemIDplus
Prostin	ChemIDplus
Prostin E2	KEGG DRUG

Manual Xrefs	Databases
913	DrugCentral
C00584	KEGG COMPOUND
D00079	KEGG DRUG
DB00917	DrugBank
DE2011969	Patent
FDB022498	FooDB
GB851827	Patent
HMDB0001220	HMDB
LMFA03010003	LIPID MAPS
LSM-42919	LINCS
NL6505799	Patent
P2E	PDBeChem
Prostaglandin_E2	Wikipedia
US3598858	Patent
View more database links

Registry Numbers	Types	Sources
2224724	Beilstein Registry Number	Beilstein
2224724	Reaxys Registry Number	Reaxys
363-24-6	CAS Registry Number	KEGG COMPOUND
363-24-6	CAS Registry Number	ChemIDplus

Citations	Types	Sources
11279302	PubMed citation	Europe PMC
12746806	PubMed citation	Europe PMC
12859290	PubMed citation	Europe PMC
14499495	PubMed citation	Europe PMC
14535055	PubMed citation	Europe PMC
14703707	PubMed citation	Europe PMC
15542928	PubMed citation	Europe PMC
15661432	PubMed citation	Europe PMC
16405508	PubMed citation	Europe PMC
16787416	PubMed citation	Europe PMC
16978535	PubMed citation	Europe PMC
20671299	PubMed citation	Europe PMC
2403792	PubMed citation	Europe PMC
24501112	PubMed citation	Europe PMC
32898608	PubMed citation	Europe PMC
33271839	PubMed citation	Europe PMC
33559528	PubMed citation	Europe PMC
33685091	PubMed citation	Europe PMC
33715333	PubMed citation	Europe PMC
33782420	PubMed citation	Europe PMC
33811074	PubMed citation	Europe PMC
33958485	PubMed citation	Europe PMC
34065827	PubMed citation	Europe PMC
34071686	PubMed citation	Europe PMC
34102274	PubMed citation	Europe PMC
6317292	PubMed citation	Europe PMC
7224729	PubMed citation	Europe PMC
74611	PubMed citation	Europe PMC
7836930	PubMed citation	Europe PMC
9276764	PubMed citation	Europe PMC

Last Modified

09 June 2021

CHEBI:15551 - prostaglandin E2

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CHEBI:15551 - prostaglandin E₂