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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL413
CHEMBL413
Compound Name SIROLIMUS
ChEMBL Synonyms WY-090217 | RAPAMUNE | SIROLIMUS | RAPAMYCIN | AY-22989
Max Phase 4 (Approved)
Trade Names RAPAMUNE | SIROLIMUS
Molecular Formula C51H79NO13

Additional synonyms for CHEMBL413 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(/C)\[C@@ ...
Download SMILES
Standard InChI InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38- ...
Download InChI
Standard InChI Key QFJCIRLUMZQUOT-HPLJOQBZSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • 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


CHEMBL413

Molecule Features

CHEMBL413 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
FK506-binding protein 1A inhibitor FK506-binding protein 1A DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
CarcinomaD002277EFO:0000313carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
Glomerulonephritis, IGAD005922EFO:0004194IGA glomerulonephritis2ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma2ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome2ClinicalTrials
PemphigusD010392EFO:0004719pemphigus vulgaris0ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Vascular MalformationsD054079EFO:0006888vascular malformation2ClinicalTrials
Coronary RestenosisD023903EFO:0004224Coronary Restenosis2ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
HypertensionD006973EFO:0000537hypertension2ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease3ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma1ClinicalTrials
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma2ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma2ClinicalTrials
Severe Combined ImmunodeficiencyD016511Orphanet:183660Severe combined immunodeficiency2ClinicalTrials
Sturge-Weber SyndromeD013341Orphanet:3205Sturge-Weber syndrome2ClinicalTrials
UveitisD014605EFO:1001231uveitis3ClinicalTrials
Uveitis, PosteriorD015866EFO:1001119posterior uveitis2ClinicalTrials
Anemia, AplasticD000741EFO:0006927severe aplastic anemia2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression2ClinicalTrials
FibromaD005350EFO:0002424fibroma3ClinicalTrials
LymphangioleiomyomatosisD018192Orphanet:538Lymphangioleiomyomatosis3ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma2ClinicalTrials
Polycystic Kidney, Autosomal DominantD016891EFO:1001496Autosomal dominant polycystic kidney disease3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
ScleritisD0154231ClinicalTrials
Diabetic RetinopathyD003930EFO:0003770diabetic retinopathy2ClinicalTrials
DyspneaD0044173ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease4ATC
Intracranial Arteriovenous MalformationsD002538Orphanet:46724Cerebral arteriovenous malformation2ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm2ClinicalTrials
Neurofibromatosis 1D009456Orphanet:636Neurofibromatosis type 12ClinicalTrials
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease3ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
Adenomatous Polyposis ColiD011125Orphanet:733Familial adenomatous polyposis2ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis2ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Birt-Hogg-Dube SyndromeD058249EFO:1001273Birt-Hogg-Dube Syndrome3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma1ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease3ClinicalTrials
Hematologic DiseasesD006402HP:0001871abnormality of blood and blood-forming tissues2ClinicalTrials
HypercholesterolemiaD006937HP:0003124hypercholesterolemia1ClinicalTrials
Macular DegenerationD008268EFO:0001365age-related macular degeneration2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma1ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma1ClinicalTrials
Cardiovascular AbnormalitiesD018376HP:0001626Abnormality of the cardiovascular system3ClinicalTrials
Coronary StenosisD023921EFO:1000882coronary stenosis3ClinicalTrials
Glycogen Storage Disease Type IID006009Orphanet:365Glycogen storage disease due to acid maltase deficiency1ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection1ClinicalTrials
Lichen PlanusD008010EFO:1000726lichen planus3ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
Pachyonychia CongenitaD053549Orphanet:2309Pachyonychia congenita1ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer1ClinicalTrials
SarcopeniaD055948EFO:1000653sarcopenia1ClinicalTrials
Uveitis, AnteriorD014606EFO:1000811anterior uveitis1ClinicalTrials
Uveitis, IntermediateD015867EFO:1000986intermediate uveitis2ClinicalTrials
AgingD000375GO:0007568aging2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Dry Eye SyndromesD015352EFO:1000906dry eye syndrome2ClinicalTrials
Fanconi AnemiaD005199Orphanet:84Fanconi anemia2ClinicalTrials
Glomerulosclerosis, Focal SegmentalD005923EFO:0004236focal segmental glomerulosclerosis2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Myositis, Inclusion BodyD018979EFO:0007323inclusion body myositis2ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia2ClinicalTrials
Anemia, AplasticD000741HP:0001915aplastic anemia2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Liver DiseasesD008107EFO:0001421liver disease2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis1ClinicalTrials
PinealomaD010871EFO:1000475Pineoblastoma2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia2ClinicalTrials
Skin NeoplasmsD012878EFO:0004198skin neoplasm3ClinicalTrials

Clinical Data

ClinicalTrials.gov SIROLIMUS
The Cochrane Collaboration SIROLIMUS

Metabolites for CHEMBL413

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
914.2 913.5551 6.18 6 195.43 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
13 3 3 14 3 3


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
10.4 - 4.26 4.26 0 65 0.16

Structural Alerts

There are 5 structural alerts for CHEMBL413. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01X - OTHER OPHTHALMOLOGICALS
S01XA - Other ophthalmologicals
S01XA23 - sirolimus

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AA - Selective immunosuppressants
L04AA10 - sirolimus

ChemSpider ChemSpider:QFJCIRLUMZQUOT-HPLJOQBZSA-N
DailyMed sirolimus
PubChem SID: 124886754 SID: 144204421 SID: 144206303 SID: 50103901
Wikipedia Sirolimus

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL413



ACToR 53123-88-9
Atlas rapamycin sirolimus
BindingDB 36609 50064359
Brenda 196831 133748
ChEBI 9168
DrugBank DB00877
DrugCentral 2446
eMolecules 30264609 31590036 594011 36500353
EPA CompTox Dashboard DTXSID5023582
FDA SRS W36ZG6FT64
Guide to Pharmacology 6031
IBM Patent System DD96757EAD306DCB93478381A36D37DA
KEGG Ligand C07909
LINCS LSM-42782
Metabolights MTBLC9168
MolPort MolPort-003-959-433
PDBe RAP
PubChem 5284616
PubChem: Drugs of the Future 12014635
PubChem: Thomson Pharma 14816426 14816423
Selleck Rapamycin
SureChEMBL SCHEMBL3463
ZINC ZINC000169289388

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