NORETHINDRONE

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII T18F433X4S
EPA CompTox DTXSID9023380

Structure

InChI Key VIKNJXKGJWUCNN-XGXHKTLJSA-N
Smiles C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
InChI
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H26O2
Molecular Weight 298.43
AlogP 3.49
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 22.0

Pharmacology

Mechanism of Action Action Reference
Progesterone receptor agonist AGONIST PubMed PubMed PubMed PubMed
Protein: Progesterone receptor
Description: Progesterone receptor
Organism : Homo sapiens
P06401 ENSG00000082175
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Secreted protein
- - 11 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- - 1 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 2
- - 1 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
2 3 0 2 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 120 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 110
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 18460-45000 - - -
Assay Description Organism Bioactivity Reference
Equilibrium dissociation constant for rat uterine estrogen receptor binding [3H]estradiol Rattus norvegicus 0.63 nM
Agonistic activity was measured for modulation of hPR-B (human progesterone receptor) in co-transfected CV-1 cells. Homo sapiens 2.2 nM
Binding affinity against Progesterone receptor in human TE85 osteosarcoma cells was determined using (Z)-[125I]-17-alpha-(2-iodovinyl)-19-nor-testosterone as radioligand None 3.2 nM
The binding affinity measured using baculovirus-expressed hPR-A in sf21 cells. Homo sapiens 1.87 nM
Dissociation constant for progesterone receptor None 0.4 nM
Inhibitory concentration against recombinant rat androgen receptor expressed in Escherichia coli using [3H]methyltrienolone (R 1881) Rattus norvegicus 120.23 nM
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 10.72 nM
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 9.342 nM DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 1.218 nM
DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 22.0 nM DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 15.0 nM
DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 808.0 nM DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 231.0 nM
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 433.0 nM DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 197.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 91.27 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 109.84 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -0.74 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.04 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 6.67 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.59 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 8.92 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.82 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.28 %
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 1.01 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.796 %
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 0.23 % 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 0.23 %

Related Entries

Cross References

Resources Reference
ChEBI 7627
ChEMBL CHEMBL1162
DrugBank DB00717
DrugCentral 1962
FDA SRS T18F433X4S
Human Metabolome Database HMDB0014855
Guide to Pharmacology 2880
KEGG C05028
PDB NDR
PharmGKB PA450651
PubChem 6230
SureChEMBL SCHEMBL23390
ZINC ZINC000085205451
CONTENTS