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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1201129
CHEMBL1201129
Compound Name DECITABINE
ChEMBL Synonyms DAC | DACOGEN | DECITABINE
Max Phase 4 (Approved)
Trade Names DACOGEN | DECITABINE
Molecular Formula C8H12N4O4

Additional synonyms for CHEMBL1201129 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2
Standard InChI InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16 ...
Download InChI
Standard InChI Key XAUDJQYHKZQPEU-KVQBGUIXSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • 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


CHEMBL1201129

Molecule Features

CHEMBL1201129 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed
DNA (cytosine-5)-methyltransferase 1 inhibitor DNA (cytosine-5)-methyltransferase 1 DailyMed
DNA (cytosine-5)-methyltransferase 3A inhibitor DNA (cytosine-5)-methyltransferase 3A DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
ThrombocytopeniaD013921HP:0001873thrombocytopenia3ClinicalTrials
Adenocarcinoma, FollicularD018263EFO:0000501follicular thyroid carcinoma2ClinicalTrials
Anemia, Refractory, with Excess of BlastsD000754EFO:0003811refractory anemia with excess blasts4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma1ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Thyroid NeoplasmsD013964EFO:0000641papillary thyroid carcinoma2ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma1ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-LymphomaD054218EFO:1001830precursor T-cell lymphoblastic leukemia-lymphoma1ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma1ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma0ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder1ClinicalTrials
Purpura, Thrombocytopenic, IdiopathicD016553EFO:0007160autoimmune thrombocytopenic purpura3ClinicalTrials
Leukemia, Myelomonocytic, ChronicD015477EFO:1001779chronic myelomonocytic leukemia4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma1ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma1ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia1ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia1ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells0ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
ThalassemiaD013789EFO:1001996Thalassemia2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia1ClinicalTrials

Clinical Data

ClinicalTrials.gov DECITABINE
The Cochrane Collaboration DECITABINE

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 CHEMBL1201129. 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
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL2966 Adenosine deaminase Bos taurus 1.000
CHEMBL5720 P2Y purinoceptor 1 Meleagris gallopavo 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.996
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 0.993
CHEMBL3415 Thymidine kinase Human herpesvirus 2 0.993
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.989
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 0.987
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.973
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 0.951
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 0.794
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.704
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.254
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.216
CHEMBL1781 DNA topoisomerase I Homo sapiens 0.202



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL2966 Adenosine deaminase Bos taurus 1.000
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL2883 Thymidine kinase, cytosolic Homo sapiens 1.000
CHEMBL2361 Thymidylate kinase Mycobacterium tuberculosis 1.000
CHEMBL5720 P2Y purinoceptor 1 Meleagris gallopavo 1.000
CHEMBL3415 Thymidine kinase Human herpesvirus 2 1.000
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 1.000
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.999
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 0.996
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 0.992
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 0.987
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 0.983
CHEMBL2284 Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens 0.963
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.936
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.935
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.870
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.865

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
228.2 228.0859 -2.14 2 123.49 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 3 0 8 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 3.49 -1.87 -1.87 1 16 0.53

Structural Alerts

There are no structural alerts for CHEMBL1201129

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC08 - decitabine

ChemSpider ChemSpider:XAUDJQYHKZQPEU-KVQBGUIXSA-N
DailyMed decitabine
PubChem SID: 144205864 SID: 170465126 SID: 47211573 SID: 56324652 SID: 57260149
Wikipedia Decitabine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1201129



ACToR 2353-33-5
Atlas 5-aza-2'-deoxycytidine 5-aza-2-deoxycytidine 2'-deoxy-5-azacytidine decitabine
BindingDB 96274
Brenda 139448 8386 72349 32104 155255 144134
ChEBI 50131
ChemicalBook CB6284800
DrugBank DB01262
DrugCentral 790
eMolecules 478929
EPA CompTox Dashboard DTXSID7030432
FDA SRS 776B62CQ27
Guide to Pharmacology 6805
Human Metabolome Database HMDB0015391
IBM Patent System DABA2B28DC9BF8B5C0AF930D174BCE19
LINCS LSM-5855
MolPort MolPort-003-925-958
Nikkaji J91.053H
PharmGKB PA164749631
PubChem 451668
PubChem: Drugs of the Future 12013916
PubChem: Thomson Pharma 14798099 14749266
Selleck Decitabine
SureChEMBL SCHEMBL4006
ZINC ZINC000016929327

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