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Also known as: Pge3, 802-31-3, Zed6sbl53s, 9-oxo-11r,15s-dihydroxy-5z,13e,17z-prostatrienoic acid, Chebi:28031, (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3s,5z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acid

Molecular Formula

C₂₀H₃₀O₅

Molecular Weight

350.4 g/mol

InChI Key

CBOMORHDRONZRN-QLOYDKTKSA-N

FDA UNII

ZED6SBL53S

Prostaglandin E3 is an eicosanoid that is generated by the action of cyclooxygenases on the omega-3 fatty acid eicosapentaenoic acid (EPA). Prostaglandin E3 regulates ocular pressure, exerts anti-inflammatory activities and may inhibit tumor cell proliferation. Prostaglandin E3 may be used as a biomarker for EPA to evaluate the association between EPA and its antineoplastic activity.

1 2D Structure

Prostaglandin E3

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acid

2.1.2 InChI

InChI=1S/C20H30O5/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/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1

2.1.3 InChI Key

CBOMORHDRONZRN-QLOYDKTKSA-N

2.1.4 Canonical SMILES

CCC=CCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

ZED6SBL53S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Delta(17)-pge1

2. Delta(17)-prostaglandin E1

3. Pge1, Delta(17)-

4. Pge3

2.3.2 Depositor-Supplied Synonyms

1. Pge3

2. 802-31-3

3. Zed6sbl53s

4. 9-oxo-11r,15s-dihydroxy-5z,13e,17z-prostatrienoic Acid

5. Chebi:28031

6. (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3s,5z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic Acid

7. Prosta-5,13,17-trien-1-oicacid, 11,15-dihydroxy-9-oxo-, (5z,11a,13e,15s,17z)-

8. Delta(17)-pge1

9. Pge1, Delta(17)-

10. Prosta-5,13,17-trien-1-oic Acid, 11,15-dihydroxy-9-oxo-, (5z,11.alpha.,13e,15s,17z)-

11. Delta(17)-prostaglandin E1

12. (-)-prostaglandin E3

13. Unii-zed6sbl53s

14. Schembl3366416

15. Chembl2074717

16. Dtxsid301045731

17. Zinc4097122

18. Lmfa03010135

19. C06439

20. Sr-01000946848

21. Sr-01000946848-1

22. Q15708280

23. 9-oxo-11alpha,15s-dihydroxy-prosta-5z,13e,17z-trien-1-oic Acid

24. 7-[3-hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoate

25. (5z,11alpha,13e,15s,17z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic Acid

26. (5z,13e,15s,17z)-11alpha,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic Acid

27. 7-[3-hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic Acid

28. 7-[3-hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic Acid Stereoisomer

29. Prosta-5,13,17-trien-1-oic Acid, 11,15-dihydroxy-9-oxo-, (5z,11alpha,13e,15s,17z)-

30. (5z,11.alpha.,13e,15s,17z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₀O₅
Molecular Weight	350.4 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	11
Exact Mass	350.20932405 g/mol
Monoisotopic Mass	350.20932405 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	506
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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