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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL53463
CHEMBL53463
Compound Name DOXORUBICIN
ChEMBL Synonyms Rubex | Doxorubicin Trifluoroacetate | Adriamycin rdf | DOXIL | CAELYX | Hydroxydaunorubicin | Doxil | DOXORUBICIN | Adriamycin | ADRIAMYCIN | DOXIL (LIPOSOMAL) | DOXORUBICIN HYDROCHLORIDE (LIPOSOMAL) | MYOCET | ADRIBLASTINA | ADRIAMYCIN PFS | RUBEX | Doxorubicin Hydrochloride
Max Phase 4 (Approved)
Trade Names MYOCET | DOXORUBICIN HYDROCHLORIDE (LIPOSOMAL) | ADRIBLASTINA | ADRIAMYCIN | DOXIL (LIPOSOMAL) | Adriamycin rdf | CAELYX | DOXIL | DOXORUBICIN HYDROCHLORIDE | RUBEX | ADRIAMYCIN PFS
Molecular Formula C27H29NO11

Additional synonyms for CHEMBL53463 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H]( ...
Download SMILES
Standard InChI InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27( ...
Download InChI
Standard InChI Key AOJJSUZBOXZQNB-TZSSRYMLSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • FDA Approval Packages
  • Gene Expression Atlas Compounds
  • Harvard Malaria Screening
  • HeCaToS Compounds
  • Open TG-GATEs
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL53463

Molecule Features

CHEMBL53463 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA FDA
DNA topoisomerase II alpha inhibitor DNA topoisomerase II alpha FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AmyloidosisD000686Orphanet:314701Primary systemic amyloidosis1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Rhabdomyosarcoma, EmbryonalD018233EFO:0000437embryonal rhabdomyosarcoma2ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma2ClinicalTrials
Choroid Plexus NeoplasmsD016545EFO:0007206choroid plexus cancer3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia3ClinicalTrials
ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma1ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma3ClinicalTrials
ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
ClinicalTrials
NeutropeniaD0095032ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
ClinicalTrials
Sarcoma, KaposiD012514EFO:0000558Kaposi's sarcoma3ClinicalTrials
ClinicalTrials
Triple Negative Breast NeoplasmsD064726EFO:0005537triple-negative breast cancer3ClinicalTrials
ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma1ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma3ClinicalTrials
ClinicalTrials
LeiomyosarcomaD007890EFO:0000564leiomyosarcoma3ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma2ClinicalTrials
ClinicalTrials
MesotheliomaD008654EFO:0000770malignant pleural mesothelioma2ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm3ClinicalTrials
ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
RhabdomyosarcomaD012208EFO:0002918rhabdomyosarcoma2ClinicalTrials
ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
ClinicalTrials
Fallopian Tube NeoplasmsD005185EFO:1000251Fallopian Tube Carcinoma2ClinicalTrials
HepatoblastomaD018197EFO:1000292Hepatoblastoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma2ClinicalTrials
ClinicalTrials
Carcinoma, Adenoid CysticD003528EFO:0000231adenoid cystic carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma3ClinicalTrials
ClinicalTrials
RetinoblastomaD012175Orphanet:790Retinoblastoma3ClinicalTrials
ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma3ClinicalTrials
ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm3ClinicalTrials
ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma3ClinicalTrials
Carcinoma, DuctalD044584EFO:0000430ductal adenocarcinoma2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma3ClinicalTrials
ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ClinicalTrials
ATC
ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
ClinicalTrials
Purpura, Thrombocytopenic, IdiopathicD016553EFO:0007160autoimmune thrombocytopenic purpura2ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm3ClinicalTrials
Lymphohistiocytosis, HemophagocyticD051359Orphanet:158038Primary hemophagocytic lymphohistiocytosis3ClinicalTrials
ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma3ClinicalTrials
ClinicalTrials
Salivary Gland NeoplasmsD012468EFO:0003826salivary gland neoplasm2ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor3ClinicalTrials
Ureteral NeoplasmsD014516EFO:0003844ureteral neoplasm2ClinicalTrials
Hereditary Breast and Ovarian Cancer SyndromeD061325Orphanet:145Hereditary breast and ovarian cancer syndrome2ClinicalTrials
Immunoblastic LymphadenopathyD007119EFO:0000255angioimmunoblastic T-cell lymphoma3ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia3ClinicalTrials
ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
ClinicalTrials
Adrenocortical CarcinomaD018268EFO:0003093adrenocortical carcinoma3ClinicalTrials
Rhabdomyosarcoma, AlveolarD018232EFO:0000248alveolar rhabdomyosarcoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm3ClinicalTrials
ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma3ClinicalTrials
ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000094B-cell acute lymphoblastic leukemia3ClinicalTrials
ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia2ClinicalTrials
Lymphoproliferative DisordersD0082322ClinicalTrials
OligodendrogliomaD009837EFO:0000632oligodendroglioma1ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary3ClinicalTrials
ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma2ClinicalTrials
ClinicalTrials
HistiocytomaD051642EFO:0005561histiocytoma3ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials

Clinical Data

ClinicalTrials.gov DOXORUBICIN
The Cochrane Collaboration DOXORUBICIN

Metabolites for CHEMBL53463

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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 CHEMBL53463. 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
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000
CHEMBL4372 Anthrax lethal factor Bacillus anthracis 0.878
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.835
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.551

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 1.000
CHEMBL5401 Signal transducer and activator of transcription 6 Homo sapiens 1.000
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 1.000
CHEMBL1806 DNA topoisomerase II alpha Homo sapiens 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 1.000
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 0.999
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 0.997
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.958

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
543.5 543.1741 0 5 206.07 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
12 6 3 12 7 3


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
7.35 8.68 .24 -1.47 2 39 0.24

Structural Alerts

There are 10 structural alerts for CHEMBL53463. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01D - CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
L01DB - Anthracyclines and related substances
L01DB01 - doxorubicin

ChemSpider ChemSpider:AOJJSUZBOXZQNB-TZSSRYMLSA-N
DailyMed doxorubicin hydrochloride
PubChem SID: 124886887 SID: 124886893 SID: 164339434
Wikipedia Doxorubicin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL53463



ACToR 111266-55-8 23214-92-8
Atlas doxorubicin
BindingDB 22984 32022
Brenda 832 32211 49017 2134
ChEBI 28748
DrugBank DB00997
DrugCentral 960
eMolecules 36788175
EPA CompTox Dashboard DTXSID8021480
FDA SRS 80168379AG
Guide to Pharmacology 7069
Human Metabolome Database HMDB0015132
IBM Patent System 1AD177E95FA84C1084894A6E5A38C6E7
KEGG Ligand C01661
LINCS LSM-4062
LipidMaps LMPK13050001
Mcule MCULE-4188577717
Metabolights MTBLC28748
MolPort MolPort-006-124-025
Nikkaji J3.792C
PDBe DM2
PharmGKB PA449412
PubChem 31703
PubChem: Thomson Pharma 14910387 14910388
SureChEMBL SCHEMBL3243
ZINC ZINC000003918087

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