ISOTRETINOIN

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC D10AD04 D10BA01
UNII EH28UP18IF
EPA CompTox DTXSID4023177

Structure

InChI Key SHGAZHPCJJPHSC-XFYACQKRSA-N
Smiles CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)CCC1
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H28O2
Molecular Weight 300.44
AlogP 5.6
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Retinoic acid receptor agonist AGONIST PubMed
Protein: Retinoic acid receptor
Description: Retinoic acid receptor alpha
Organism : Homo sapiens
P10276 ENSG00000131759
Protein: Retinoic acid receptor
Description: Retinoic acid receptor beta
Organism : Homo sapiens
P10826 ENSG00000077092
Protein: Retinoic acid receptor
Description: Retinoic acid receptor gamma
Organism : Homo sapiens
P13631 ENSG00000172819
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 1
Enzyme Lyase
- - - - 72-96
Other cytosolic protein
- 900-900 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 32
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 37100-37100 - - -
Assay Description Organism Bioactivity Reference
Inhibition of binding to chick skin Cytoplasmic retinoic acid binding protein Gallus gallus 900.0 nM
Tested for its ability to inhibit the binding of (all-E-)-RA to cytoplasmic retinoic acid-binding protein (CRABP) from chick skin Gallus gallus 900.0 nM
Binding affinity for mouse Cytoplasmic retinoic acid binding protein type 1 Mus musculus 200.0 nM
Binding affinity for mouse Cytoplasmic retinoic acid binding protein type 2 Mus musculus 200.0 nM
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J43 at a concentration of 10E-6 M. Homo sapiens 109.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J43 at a concentration of 10E-7 M. Homo sapiens 100.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J83 at a concentration of 10E-6 M. Homo sapiens 94.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J83 at a concentration of 10E-7 M. Homo sapiens 86.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J84 at a concentration of 10E-6 M. Homo sapiens 87.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J84 at a concentration of 10E-7 M. Homo sapiens 52.0 %
The compound was tested for the normalized percent inhibition of CFU-GM colony growth of JMML cells of patient J84 at a concentration of 10e-8 M. Homo sapiens 5.0 %
Tested for its concentration necessary to achieve a 50% reduction in absolute cell number compared to vehicle-treated controls using human sebaceous cell assay Homo sapiens 100.0 nM
Percent inhibition of TPA-induced ornithine decarboxylase activity Mus musculus 96.0 %
Percent inhibition was determined by mouse skin ornithine decarboxylase (ODC) assay using [14C]-ornithine None 72.0 %
DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 462.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 848.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 540.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 11.5 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 0.91 %
Cytotoxicity against human MRC5 cells assessed as reduction of cell viability at 1 uM after 96 hrs by alamar blue assay Homo sapiens 10.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 32.24 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 51.47 %
Inhibition of purified recombinant FASN TE activity (unknown origin) using 4-MUH as substrate preincubated for 30 mins before substrate addition measured after 1 hr by fluorescence assay Homo sapiens 40.0 %
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 49.4 nM
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 5.02 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -1.2 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 9.94 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 3.08 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 13.74 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.42 %
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 -2.4 %
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 6.5 %
Antagonist activity at PSGR/OR51E2 (unknown origin) expressed in human Hana3A cells co-transfected with CRE-Luc by luciferase reporter gene assay Homo sapiens 160.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.34 %
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 -0.14 % 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 -0.14 %

Related Entries

Cross References

Resources Reference
ChEBI 6067
ChEMBL CHEMBL547
DrugBank DB00982
DrugCentral 1508
FDA SRS EH28UP18IF
Human Metabolome Database HMDB0006219
Guide to Pharmacology 7600
KEGG C07058
PDB REA
PubChem 5282379
SureChEMBL SCHEMBL38299
ZINC ZINC000003792789
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