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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL547
CHEMBL547
Compound Name ISOTRETINOIN
ChEMBL Synonyms AMNESTEEM | ISOTRETINOIN | ACCUTANE | CLARAVIS | ABSORICA | ZENATANE | ISOTREX | ROACCUTANE | MYORISAN | 13 Cis-Retinoic Acid | SOTRET | RO 4-3780
Max Phase 4 (Approved)
Trade Names AMNESTEEM | ABSORICA | ISOTREX | ZENATANE | MYORISAN | ROACCUTANE | SOTRET | CLARAVIS | ACCUTANE
Molecular Formula C20H28O2

Additional synonyms for CHEMBL547 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C\C(=C\C(=O)O)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Standard InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3 ...
Download InChI
Standard InChI Key SHGAZHPCJJPHSC-XFYACQKRSA-N

Sources

  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL547

Molecule Features

CHEMBL547 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:Y Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoic acid receptor agonist Retinoic acid receptor PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
GliosarcomaD018316EFO:1001465gliosarcoma1ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia1ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia1ClinicalTrials
Acne VulgarisD000152EFO:0003894acne4ATC
ATC
ATC
ClinicalTrials
Epidermolysis BullosaD004820EFO:1000690epidermolysis bullosa1ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma1ClinicalTrials
OligodendrogliomaD009837EFO:0002501anaplastic oligodendroglioma1ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma1ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection2ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia2ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia1ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
InfectionD007239EFO:0000544infection1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma1ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor1ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
Glomerulosclerosis, Focal SegmentalD005923EFO:0004236focal segmental glomerulosclerosis2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer3ClinicalTrials
Keratosis, ActinicD055623EFO:0002496actinic keratosis2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
RosaceaD012393EFO:1000760rosacea3ClinicalTrials

Clinical Data

ClinicalTrials.gov ISOTRETINOIN
The Cochrane Collaboration ISOTRETINOIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL547. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.998
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.954
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.922
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.843
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.739
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.445
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 0.286
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.273



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.999
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.995
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.995
CHEMBL1075315 C-X-C chemokine receptor type 5 Homo sapiens 0.883
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.881
CHEMBL3091268 Nuclear receptor ROR-beta Homo sapiens 0.874
CHEMBL4804 Dual specificity phosphatase Cdc25B Homo sapiens 0.678
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.637

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
300.4 300.2089 5.6 5 37.3 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 1 2 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.76 - 6.26 3.66 0 22 0.53

Structural Alerts

There are 9 structural alerts for CHEMBL547. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD54 - isotretinoin, combinations

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD04 - isotretinoin

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10B - ANTI-ACNE PREPARATIONS FOR SYSTEMIC USE
D10BA - Retinoids for treatment of acne
D10BA01 - isotretinoin

ChemSpider ChemSpider:SHGAZHPCJJPHSC-XFYACQKRSA-N
DailyMed isotretinoin
PubChem SID: 144207291 SID: 26747659 SID: 26753641 SID: 26753642 SID: 26753643 SID: 26753644 SID: 47193696 SID: 50106981 SID: 90341473
Wikipedia Isotretinoin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL547



ACToR 97950-17-9
Atlas 13-cis retinoic acid
BindingDB 50031459
Brenda 10467 71524
CarotenoidDB CA01204
ChEBI 6067
DrugBank DB00982
DrugCentral 1508
eMolecules 1934465
EPA CompTox Dashboard DTXSID4023177
FDA SRS EH28UP18IF
Guide to Pharmacology 7600
Human Metabolome Database HMDB0006219
IBM Patent System 88C31C9E1A6E7C3702CD5897A78D59B6
LINCS LSM-42855
LipidMaps LMPR01090021
Metabolights MTBLC6067
MolPort MolPort-003-666-394
NIH Clinical Collection SAM002548955
Nikkaji J8.772F J1.313.475H
PubChem 5282379
PubChem: Drugs of the Future 12013352
PubChem: Thomson Pharma 14751738
SureChEMBL SCHEMBL38299
ZINC ZINC000003792789

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/SHGAZHPCJJPHSC-XFYACQKRSA-N spacer
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