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15 (R) -Prostaglandin E2

CAT: 0931-T84587-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-T84587-01Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
38873-82-4
Target
Others, Prostaglandin Receptor
Related Pathways
GPCR/G Protein, Immunology/Inflammation, Others
Bioactivity
15 (R) -Prostaglandin E2, the C-15 epimer of the more physiologically abundant 15 (S) -PGE2 (sc-201225) isomer, is produced mainly from arachidonic acid (sc-200770) via the action of COX and PGES enzymes. Present in nearly all cell types, PGE2 interacts with four distinct receptors, EP1 to EP4, leading to a wide range of biological effects. However, 15 (R) -Prostaglandin E2 exhibits significantly lower efficacy in most biological assays compared to its 15 (S) counterpart. Notably, acid catalyzed epimerization can transform 15 (R) -Prostaglandin E2 into the more active 15 (S) -Prostaglandin E2 form.
Smiles
CCCCC[C@@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
Molecular Formula
C20H32O5
Molecular Weight
352.471
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

15-epi-Prostaglandin E2
CAS Number38873-82-4
PubChem CID5283086
IUPAC Name(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Molecular FormulaC20H32O5
Molecular Weight352.5
XLogP2.8
Topological Polar Surface Area94.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count12
Heavy Atom Count25
Formal Charge0
Complexity469
SMILES
CCCCC[C@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)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-/m1/s1
InChIKey
XEYBRNLFEZDVAW-GKEZHNTDSA-N
Chemical Structure
2D Structure
2D structure of 15-epi-Prostaglandin E2
CAS: 38873-82-4
CID: 5283086
Formula: C20H32O5
MW: 352.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight352.5
XLogP32.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count12
Exact Mass352.22497412
Monoisotopic Mass352.22497412
Topological Polar Surface Area94.8 Ų
Heavy Atom Count25
Formal Charge0
Complexity469
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
T78582-0115-keto-Prostaglandin E2
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Alternative Products

CatalogName
TBI4534-5MGProstaglandin B1, Endogenous prostaglandin
TBI4461-5MGProstaglandin A1, Endogenous prostaglandin
TBI4455-10MGProstaglandin E1, Endogenous prostaglandin
AG184Prostaglandin
TBI1358-1MGProstaglandin E2, Prostaglandin E (EP) agonist
B7005-10Prostaglandin E2
HY-113481-01Prostaglandin E3
HY-B0131-01Prostaglandin E1
HY-120656-01Prostaglandin K2
HY-126819Prostaglandin H1

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