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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL803
CHEMBL803
Compound Name CYTARABINE
ChEMBL Synonyms CYTOSINE ARABINOSIDE HYDROCHLORIDE | ALEXAN | ARABINOSYL CYTOSINE | U-19,920 | CYTARABINE HYDROCHLORIDE | ARA-CYTIDINE | CYTOSAR | Tarabine PFS | U-19920A | DEPOCYT | CYTARABINE | CYTOSAR-U | ALEXAN 100 | DEPOCYTE
Max Phase 4 (Approved)
Trade Names ALEXAN 100 | CYTARABINE | CYTOSAR-U | DEPOCYTE | DEPOCYT | CYTOSAR | Tarabine PFS | ALEXAN
Molecular Formula C9H13N3O5

Additional synonyms for CHEMBL803 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O
Standard InChI InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13 ...
Download InChI
Standard InChI Key UHDGCWIWMRVCDJ-CCXZUQQUSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • 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


CHEMBL803

Molecule Features

CHEMBL803 compound icon
Drug Type:Natural Product-derived Rule of Five:Y 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
DNA polymerase (alpha/delta/epsilon) inhibitor DNA polymerase (alpha/delta/epsilon) DailyMed
RNA inhibitor RNA DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Histiocytosis, Langerhans-CellD006646EFO:1000318Langerhans Cell Histiocytosis3ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Urinary Bladder, OveractiveD053201EFO:1000781overactive bladder1ClinicalTrials
Autoimmune DiseasesD001327EFO:0005140autoimmune disease2ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis0ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
Leukemia, Basophilic, AcuteD015471EFO:0003029acute basophilic leukemia3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia2ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus2ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma3ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma2ClinicalTrials
MalariaD008288EFO:0001068malaria3ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis2ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Anemia, RefractoryD000753EFO:0003802refractory anemia2ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000094B-cell acute lymphoblastic leukemia2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0003027acute myeloblastic leukemia without maturation4ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
NeutropeniaD0095032ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
DiseaseD004194EFO:0000408disease2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia4ClinicalTrials
ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
AlopeciaD000505EFO:0004191androgenetic alopecia1ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
Leukemia, Erythroblastic, AcuteD004915EFO:1001257acute erythroblastic leukemia1ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia3ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia3ClinicalTrials
Lymphoproliferative DisordersD0082322ClinicalTrials
MelanomaD008545EFO:0000756melanoma3ClinicalTrials
Sarcoma, MyeloidD023981EFO:1000286Granulocytic Sarcoma3ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Megakaryoblastic, AcuteD007947EFO:0003025acute megakaryoblastic leukaemia3ClinicalTrials
Leukemia, Monocytic, AcuteD007948EFO:0000221acute monocytic leukemia3ClinicalTrials
Leukemia, Myelomonocytic, AcuteD015479EFO:0000223acute myelomonocytic leukemia3ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia2ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
Sarcoma, MyeloidD023981EFO:1001052myeloid sarcoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov CYTARABINE
The Cochrane Collaboration CYTARABINE

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 CHEMBL803. 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
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL3589 Adenosine kinase Homo sapiens 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 1.000
CHEMBL3884 Sodium/glucose cotransporter 2 Homo sapiens 1.000
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 1.000
CHEMBL1795117 Histone-lysine N-methyltransferase, H3 lysine-79 specific Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 1.000
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 1.000
CHEMBL4837 Adhesin protein fimH Escherichia coli K-12 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 0.997
CHEMBL255 Adenosine A2b receptor Homo sapiens 0.996
CHEMBL1781 DNA topoisomerase I Homo sapiens 0.996
CHEMBL4975 Adenosine A1 receptor Bos taurus 0.950



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL3589 Adenosine kinase Homo sapiens 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 1.000
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 1.000
CHEMBL2982 Adenosine kinase Toxoplasma gondii 1.000
CHEMBL3884 Sodium/glucose cotransporter 2 Homo sapiens 1.000
CHEMBL4518 Purinergic receptor P2Y14 Homo sapiens 1.000
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 1.000
CHEMBL1795117 Histone-lysine N-methyltransferase, H3 lysine-79 specific Homo sapiens 1.000
CHEMBL255 Adenosine A2b receptor Homo sapiens 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 1.000
CHEMBL2966 Adenosine deaminase Bos taurus 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
243.2 243.0855 -2.56 2 130.83 NEUTRAL


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.48 4.26 -1.81 -1.81 1 17 0.45

Structural Alerts

There are no structural alerts for CHEMBL803

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC01 - cytarabine

ChemSpider ChemSpider:UHDGCWIWMRVCDJ-CCXZUQQUSA-N
DailyMed cytarabine
PubChem SID: 131404637 SID: 144204754 SID: 144212288 SID: 26719755 SID: 29215144 SID: 47193873 SID: 90341066
Wikipedia Cytarabine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL803



ACToR 147-94-4
Atlas Ara-C cytarabine
BindingDB 50087289
Brenda 2016 153431 151038 32999 18270 2681 206941 92471 22093 35304 148756 92473 154421
ChEBI 28680
DrugBank DB00987
DrugCentral 770
eMolecules 1012736
EPA CompTox Dashboard DTXSID3022877
FDA SRS 04079A1RDZ
Guide to Pharmacology 4827
Human Metabolome Database HMDB0015122 HMDB0000089
IBM Patent System 876328D8D0EB57775D3A184BA566EE9A
KEGG Ligand C02961
LINCS LSM-5470
Mcule MCULE-3945147956
MolPort MolPort-001-792-509
NIH Clinical Collection SAM001247012
Nikkaji J2.958K
PDBe AR3
PharmGKB PA449177
PubChem 6253
PubChem: Thomson Pharma 14774115 15196510
Selleck Cytarabine(Cytosar-U)
SureChEMBL SCHEMBL3140
ZINC ZINC000003795098

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