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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL713
CHEMBL713
Compound Name ENTECAVIR
ChEMBL Synonyms BARACLUDE | ENTECAVIR | SQ34676 | BMS-200475-01
Max Phase 4 (Approved)
Trade Names ENTECAVIR | BARACLUDE
Molecular Formula C12H15N5O3

Additional synonyms for CHEMBL713 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=Nc2c(ncn2[C@H]3C[C@H](O)[C@@H](CO)C3=C)C(=O)N1
Standard InChI InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)1 ...
Download InChI
Standard InChI Key QDGZDCVAUDNJFG-FXQIFTODSA-N

Sources

  • British National Formulary
  • 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


CHEMBL713

Molecule Features

CHEMBL713 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA polymerase/reverse transcriptase inhibitor DNA polymerase/reverse transcriptase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm2ClinicalTrials
Hepatitis B, ChronicD019694EFO:0004239chronic hepatitis B infection3ClinicalTrials
Hepatitis B, ChronicD019694EFO:0004197hepatitis B infection3ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm2ClinicalTrials
Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection2ClinicalTrials
Liver FailureD0170932ClinicalTrials
Hepatitis DD003699EFO:0007304hepatitis D2ClinicalTrials

Clinical Data

ClinicalTrials.gov ENTECAVIR
The Cochrane Collaboration ENTECAVIR

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 CHEMBL713. 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
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 1.000
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 1.000
CHEMBL2360 Hypoxanthine-guanine phosphoribosyltransferase Homo sapiens 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.999
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 0.999
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.999
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.999
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.998
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 0.998
CHEMBL5328 Thymidylate synthase Lactobacillus casei 0.865
CHEMBL2966 Adenosine deaminase Bos taurus 0.774
CHEMBL5720 P2Y purinoceptor 1 Meleagris gallopavo 0.718
CHEMBL3415 Thymidine kinase Human herpesvirus 2 0.698
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 0.584
CHEMBL308 Cyclin-dependent kinase 1 Homo sapiens 0.556
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 0.441
CHEMBL3712907 Transmembrane domain-containing protein TMIGD3 Homo sapiens 0.250



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2360 Hypoxanthine-guanine phosphoribosyltransferase Homo sapiens 1.000
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 1.000
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 1.000
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL2883 Thymidine kinase, cytosolic Homo sapiens 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 1.000
CHEMBL2605 Adenosine A2a receptor Cavia porcellus 1.000
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 0.998
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 0.996
CHEMBL2966 Adenosine deaminase Bos taurus 0.995
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 0.988
CHEMBL3415 Thymidine kinase Human herpesvirus 2 0.987
CHEMBL5328 Thymidylate synthase Lactobacillus casei 0.983
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 0.972
CHEMBL255 Adenosine A2b receptor Homo sapiens 0.953

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
277.3 277.1175 -0.83 2 130.05 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 4 0 8 5 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.64 2.64 -1.97 -1.98 2 20 0.53

Structural Alerts

There are 2 structural alerts for CHEMBL713. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J05 - ANTIVIRALS FOR SYSTEMIC USE
J05A - DIRECT ACTING ANTIVIRALS
J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors
J05AF10 - entecavir

ChemSpider ChemSpider:QDGZDCVAUDNJFG-FXQIFTODSA-N
DailyMed entecavir
PubChem SID: 144205745
Wikipedia Entecavir

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL713



ACToR 142217-69-4
ChEBI 473990
DrugBank DB00442
DrugCentral 1019
eMolecules 10412516
EPA CompTox Dashboard DTXSID4046446
FDA SRS NNU2O4609D
Human Metabolome Database HMDB0014585
IBM Patent System E3D5A7F874438240954E2EAF13652462
LINCS LSM-5258
MolPort MolPort-005-942-963 MolPort-006-167-546
Nikkaji J846.317D
PharmGKB PA164784025
PubChem 153941
PubChem: Drugs of the Future 12014687
PubChem: Thomson Pharma 14848612 14824340
SureChEMBL SCHEMBL28648
ZINC ZINC000003802690

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