Ketcher 06092115522D 1   1.00000     0.00000     0

 25 25  0     0  0            999 V2000
    0.0000   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171    0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262    1.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320   -2.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -1.7600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -1.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302    3.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    5.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1962   -1.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0622   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1     0  0
  9  2  1  0     0  0
  2  3  1  0     0  0
  7  3  1  0     0  0
  3  4  1  6     0  0
  1  5  2  0     0  0
  5 10  1  0     0  0
  4 22  1  0     0  0
  7  6  1  0     0  0
  6  9  1  0     0  0
  7  8  2  0     0  0
  9 12  1  6     0  0
 10 13  1  0     0  0
 10 11  1  6     0  0
 13 14  1  0     0  0
 14 23  1  0     0  0
 16 17  1  0     0  0
 17 18  1  0     0  0
 18 20  1  0     0  0
 20 19  1  0     0  0
 20 21  2  0     0  0
 15 16  1  0     0  0
 22 15  2  0     0  0
 23 24  1  0     0  0
 24 25  1  0     0  0
M  END
> <ID>
CHEBI:15551

> <NAME>
prostaglandin E2

> <DEFINITION>
Prostaglandin F2α 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.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:26323; CHEBI:10910; CHEBI:10911; CHEBI:4625; CHEBI:114125; CHEBI:8512

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

> <IUPAC_NAME>
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid

> <INN>
dinoprostonum; dinoprostone; dinoprostone; dinoprostona

> <BRAND_NAME>
Prostin E2; Prostin; Prostenone; Prostarmon E; Propess; Prepidil; Minprostin E2; Minprositin E2; Glandin-E2; Enzaprost E; Cerviprost; Cerviprime; Cervidil

> <FORMULA>
C20H32O5

> <MASS>
352.471

> <MONOISOTOPIC_MASS>
352.22497

> <CHARGE>
0

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

> <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

> <BEILSTEIN_REGISTRY_NUMBER>
2224724

> <CAS_REGISTRY_NUMBER>
363-24-6

> <REAXYS_REGISTRY_NUMBER>
2224724

> <CHEMIDPLUS>
363-24-6

> <DRUGBANK_ACCESSION>
DB00917

> <KEGG_COMPOUND_ACCESSION>
C00584

> <KEGG_DRUG_ACCESSION>
D00079

> <LINCS_ACCESSION>
LSM-42919

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMFA03010003

> <PDBECHEM_ACCESSION>
P2E

> <WIKIPEDIA_ACCESSION>
Prostaglandin_E2

> <PUBMED_CITATION>
11279302; 12746806; 12859290; 14499495; 14535055; 14703707; 15542928; 15661432; 16405508; 16787416; 16978535; 20671299; 2403792; 24501112; 32898608; 33271839; 33559528; 33685091; 33715333; 33782420; 33811074; 33958485; 34065827; 34071686; 34102274; 6317292; 7224729; 74611; 7836930; 9276764

$$$$