PGE1   Click here for help

GtoPdb Ligand ID: 1882

Synonyms: Alprostadil® | MR-256 | prostaglandin E1
Approved drug PDB Ligand
PGE1 is an approved drug (FDA (1981))
Compound class: Metabolite or derivative
Comment: PGE1 is an endogenous prostaglandin. Synthetic PGE1 is known as alprostadil. PGE1 activates prostanoid family GPCRs.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 94.83
Molecular weight 354.24
XLogP 3.31
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCCC(C=CC1C(O)CC(=O)C1CCCCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)O
InChI InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N
References
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Cloning, functional expression, and characterization of the human prostaglandin E2 receptor EP2 subtype.
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2. Boie Y, Stocco R, Sawyer N, Slipetz DM, Ungrin MD, Neuschäfer-Rube F, Püschel GP, Metters KM, Abramovitz M. (1997)
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
Eur J Pharmacol, 340 (2-3): 227-41. [PMID:9537820]
3. Borst P, de Wolf C, van de Wetering K. (2007)
Multidrug resistance-associated proteins 3, 4, and 5.
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4. Davis TL, Sharif NA. (2000)
Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.
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5. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S. (1997)
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
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6. Leduc M, Breton B, Galés C, Le Gouill C, Bouvier M, Chemtob S, Heveker N. (2009)
Functional selectivity of natural and synthetic prostaglandin EP4 receptor ligands.
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7. Lishko PV, Botchkina IL, Kirichok Y. (2011)
Progesterone activates the principal Ca2+ channel of human sperm.
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8. Maruyama T, Asada M, Shiraishi T, Ishida A, Egashira H, Yoshida H, Maruyama T, Ohuchida S, Nakai H, Kondo K et al.. (2001)
Design and synthesis of a highly selective EP4-receptor agonist. Part 1: 3,7-dithiaPG derivatives with high selectivity.
Bioorg Med Chem Lett, 11 (15): 2029-31. [PMID:11454473]
9. Pourmal S, Green E, Bajaj R, Chemmama IE, Knudsen GM, Gupta M, Sali A, Cheng Y, Craik CS, Kroetz DL et al.. (2024)
Structural basis of prostaglandin efflux by MRP4.
Nat Struct Mol Biol, [Epub ahead of print]. [PMID:38216659]
10. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P. (2003)
The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs.
Proc Natl Acad Sci USA, 100 (16): 9244-9. [PMID:12835412]
11. Sharif NA, Davis TL. (2002)
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
J Pharm Pharmacol, 54 (4): 539-47. [PMID:11999132]
12. Stitham J, Arehart E, Gleim SR, Li N, Douville K, Hwa J. (2007)
New insights into human prostacyclin receptor structure and function through natural and synthetic mutations of transmembrane charged residues.
Br J Pharmacol, 152 (4): 513-22. [PMID:17704830]
13. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW. (1998)
Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist.
Br J Pharmacol, 123 (7): 1317-24. [PMID:9579725]