DESOGESTREL

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Search structure


Synonyms	Aizea Cerazette Cerelle Desogestrel Desomono Feanolla Mircette Nacrez ORG 2969 ORG-2969 Zelleta
Status
Molecule Category	Free-form
ATC	G03AC09
UNII	81K9V7M3A3
EPA CompTox	DTXSID6022898


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RPLCPCMSCLEKRS-BPIQYHPVSA-N
Smiles	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3C(=C)C[C@@]21CC
InChI	InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H30O
Molecular Weight	310.48
AlogP	4.87
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	1.0
Polar Surface Area	20.23
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Progesterone receptor agonist	AGONIST	ISBN


Protein: Progesterone receptor Description: Progesterone receptor Organism : Homo sapiens P06401 ENSG00000082175

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor	-	-	-	-	79
Secreted protein	-	-	251	-	-

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin	Homo sapiens	251.19 nM
Antagonist activity at human recombinant dopamine D2 long receptor expressed in CHOK1 cells coexpressing mitochondrial apoaequorin assessed as inhibition of agonist-induced effect at 50 uM after 15 mins by luminometric analysis relative to haloperidol	Homo sapiens	88.0 %
Antagonist activity at human recombinant dopamine D1 receptor expressed in CHOK1 cells assessed as inhibition of agonist-induced cAMP accumulation at 100 uM preincubated for 10 mins prior to agonist addition measured after 30 mins by HTRF assay relative to SCH23390	Homo sapiens	79.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-8.93 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	26.28 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	17.1 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.35 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.35 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %

Related Entries

Cross References

Resources	Reference
ChEBI	4453
ChEMBL	CHEMBL1533
DrugBank	DB00304
DrugCentral	818
FDA SRS	81K9V7M3A3
Human Metabolome Database	HMDB0014449
Guide to Pharmacology	7065
KEGG	C07629
PharmGKB	PA449238
PubChem	40973
SureChEMBL	SCHEMBL41341
ZINC	ZINC000004097416

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).