PGF2α   Click here for help

GtoPdb Ligand ID: 1884

Synonyms: prostaglandin F2α
PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite or derivative
Comment: PGF2α is a naturally-occurring prostanoid which functions as a potent vasoconstrictor. The synthetically produced drug, dinoprost, is chemically identical to the endogenous prostaglandin [3].
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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
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 4
Rotatable bonds 12
Topological polar surface area 97.99
Molecular weight 354.24
XLogP 3.2
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(C1CC=CCCCC(=O)O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI Key PXGPLTODNUVGFL-YNNPMVKQSA-N
Classification Click here for help
Compound class Metabolite or derivative
IUPAC Name Click here for help
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
International Nonproprietary Names Click here for help
INN number INN
3074 dinoprost
Synonyms Click here for help
prostaglandin F2α
Database Links Click here for help
Specialist databases
GPCRdb Ligand PGF2alpha
Other databases
CAS Registry No. 551-11-1 (source: Scifinder)
ChEBI CHEBI:15553
ChEMBL Ligand CHEMBL815
DrugCentral Ligand 912
GtoPdb PubChem SID 135651540
PubChem CID 5280363
RCSB PDB Ligand UGU
Search Google for chemical match using the InChIKey PXGPLTODNUVGFL-YNNPMVKQSA-N
Search Google for chemicals with the same backbone PXGPLTODNUVGFL
Search PubMed clinical trials dinoprost
Search PubMed titles dinoprost
Search PubMed titles/abstracts dinoprost
UniChem Compound Search for chemical match using the InChIKey PXGPLTODNUVGFL-YNNPMVKQSA-N
UniChem Connectivity Search for chemical match using the InChIKey PXGPLTODNUVGFL-YNNPMVKQSA-N
Wikipedia Prostaglandin_F2alpha