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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL178
CHEMBL178
Compound Name DAUNORUBICIN
ChEMBL Synonyms Cerubidine | RP 13057 [AS THE BASE) | DAUNOXOME | RP-13057 | DAUNORUBICIN CITRATE | NDC 0082-4155 | DAUNORUBICIN | FI-6339 | FI 6339 [AS THE BASE] | DAUNORUBICIN HYDROCHLORIDE | CERUBIDINE
Max Phase 4 (Approved)
Trade Names DAUNOXOME | CERUBIDINE | DAUNORUBICIN HYDROCHLORIDE
Molecular Formula C27H29NO10

Additional synonyms for CHEMBL178 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/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27( ...
Download InChI
Standard InChI Key STQGQHZAVUOBTE-VGBVRHCVSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • FDA Approval Packages
  • Harvard Malaria Screening
  • HeCaToS Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • 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


CHEMBL178

Molecule Features

CHEMBL178 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 DailyMed DailyMed
DNA topoisomerase II alpha inhibitor DNA topoisomerase II alpha DailyMed DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Hepatitis B, ChronicD019694EFO:0004197hepatitis B infection3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
ClinicalTrials
Leukemia, Basophilic, AcuteD015471EFO:0003029acute basophilic leukemia3ClinicalTrials
Leukemia, Myelomonocytic, AcuteD015479EFO:0000223acute myelomonocytic leukemia3ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma1ClinicalTrials
Anemia, RefractoryD000753EFO:0003802refractory anemia2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
ClinicalTrials
ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
Leukemia, Myeloid, AcuteD015470EFO:0003027acute myeloblastic leukemia without maturation3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
ClinicalTrials
Sarcoma, MyeloidD023981EFO:1001052myeloid sarcoma3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Leukemia, Megakaryoblastic, AcuteD007947EFO:0003025acute megakaryoblastic leukaemia3ClinicalTrials
Leukemia, Monocytic, AcuteD007948EFO:0000221acute monocytic leukemia3ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia4ClinicalTrials
ClinicalTrials
FDA

Clinical Data

ClinicalTrials.gov DAUNORUBICIN
The Cochrane Collaboration DAUNORUBICIN

Metabolites for CHEMBL178

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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 CHEMBL178. 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
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.261
CHEMBL4372 Anthrax lethal factor Bacillus anthracis 0.217

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 1.000
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 1.000
CHEMBL5401 Signal transducer and activator of transcription 6 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
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 0.995
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 0.977
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.971
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.249

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
527.5 527.1791 1.03 4 185.84 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
11 5 2 11 6 3


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
7.38 8.68 .54 -1.15 2 38 0.31

Structural Alerts

There are 9 structural alerts for CHEMBL178. 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
L01DB02 - daunorubicin

ChemSpider ChemSpider:STQGQHZAVUOBTE-VGBVRHCVSA-N
DailyMed daunorubicin citrate daunorubicin hydrochloride
PubChem SID: 11114094 SID: 144204447 SID: 170465048 SID: 29215022
Wikipedia Daunorubicin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL178



ACToR 1407-15-4 11006-54-5 20830-81-3
BindingDB 32017 50368352
Brenda 48969 48970 10631 1532 96463 21578 48971
ChEBI 41977
DrugBank DB00694
DrugCentral 786
eMolecules 30152546
EPA CompTox Dashboard DTXSID7022883
FDA SRS ZS7284E0ZP
Guide to Pharmacology 7063
Human Metabolome Database HMDB0014832
IBM Patent System 73E2B53B7BE47ED0E8C6D86BE4962DB4
KEGG Ligand C01907
LINCS LSM-2962
LipidMaps LMPK13050002
Metabolights MTBLC41977
MolPort MolPort-002-533-961
Nikkaji J3.149F
PDBe DM1
PharmGKB PA449212
PubChem 30323
PubChem: Drugs of the Future 125299287
PubChem: Thomson Pharma 14763056 15481415
SureChEMBL SCHEMBL3041
ZINC ZINC000003917708

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