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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 SIROLIMUS | RAPAMUNE | WY-090217 | RAPAMYCIN | AY-22989
Max Phase 4 (Approved)
Trade Names RAPAMUNE
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
  • 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
FIBROMAD005350EFO:0002424FIBROMA1ClinicalTrials
GLIOMAD005910EFO:0000326CENTRAL NERVOUS SYSTEM CANCER1ClinicalTrials
GRAFT VS HOST DISEASED006086EFO:0004599ACUTE GRAFT VS. HOST DISEASE2ClinicalTrials
HIV INFECTIONSD015658EFO:0000180HIV-1 INFECTION1ClinicalTrials
MULTIPLE MYELOMAD009101EFO:0001378MULTIPLE MYELOMA1ClinicalTrials
RENAL INSUFFICIENCY, CHRONICD051436EFO:0003884CHRONIC KIDNEY DISEASE2ClinicalTrials
SCLERITISD015423HP:0100532SCLERITIS1ClinicalTrials
UVEITISD014605EFO:1001231UVEITIS3ClinicalTrials
CARDIOVASCULAR ABNORMALITIESD018376HP:0001626ABNORMALITY OF THE CARDIOVASCULAR SYSTEM3ClinicalTrials
LYMPHOMA, T-CELL, CUTANEOUSD016410EFO:0002913CUTANEOUS T-CELL LYMPHOMA2ClinicalTrials
PACHYONYCHIA CONGENITAD053549Orphanet:2309PACHYONYCHIA CONGENITA1ClinicalTrials
CARCINOMAD002277EFO:0000313CARCINOMA2ClinicalTrials
HYPERTENSIOND006973EFO:0000537HYPERTENSION2ClinicalTrials
CARCINOMA, HEPATOCELLULARD006528EFO:0000182HEPATOCELLULAR CARCINOMA3ClinicalTrials
DRY EYE SYNDROMESD015352EFO:1000906DRY EYE SYNDROME2ClinicalTrials
LICHEN PLANUSD008010EFO:1000726LICHEN PLANUS3ClinicalTrials
LUPUS ERYTHEMATOSUS, SYSTEMICD008180EFO:0002690SYSTEMIC LUPUS ERYTHEMATOSUS2ClinicalTrials
NEOPLASMSD009369EFO:0000616NEOPLASM1ClinicalTrials
SCLERODERMA, SYSTEMICD012595EFO:0000717SYSTEMIC SCLERODERMA1ClinicalTrials
HYPERURICEMIAD033461Orphanet:79191DISORDER OF PURINE METABOLISM2ClinicalTrials
IMMUNE SYSTEM DISEASESD007154EFO:0000540IMMUNE SYSTEM DISEASE4ATC
MULTIPLE SCLEROSIS, RELAPSING-REMITTINGD020529EFO:0003929RELAPSING-REMITTING MULTIPLE SCLEROSIS1ClinicalTrials
SARCOMAD012509EFO:0000691SARCOMA1ClinicalTrials
CROHN DISEASED003424EFO:0000384CROHN'S DISEASE2ClinicalTrials
DIABETES MELLITUS, TYPE 1D003922EFO:0001359TYPE I DIABETES MELLITUS3ClinicalTrials
NEOPLASMSD009369EFO:0000311CANCER1ClinicalTrials
PANCREATIC NEOPLASMSD010190EFO:0002618PANCREATIC CARCINOMA2ClinicalTrials
PRECURSOR CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMAD054198EFO:0000220ACUTE LYMPHOBLASTIC LEUKEMIA2ClinicalTrials
PROSTATIC NEOPLASMSD011471EFO:0001663PROSTATE CARCINOMA2ClinicalTrials
AGINGD000375GO:0007568AGING2ClinicalTrials
BREAST NEOPLASMSD001943EFO:0000305BREAST CARCINOMA2ClinicalTrials
KIDNEY DISEASESD007674EFO:0003086KIDNEY DISEASE2ClinicalTrials
MACULAR DEGENERATIOND008268EFO:0001365AGE-RELATED MACULAR DEGENERATION2ClinicalTrials
RECTAL NEOPLASMSD012004EFO:1000657RECTUM CANCER1ClinicalTrials
SKIN NEOPLASMSD012878EFO:0004198SKIN NEOPLASM3ClinicalTrials
DIABETIC RETINOPATHYD003930EFO:0003770DIABETIC RETINOPATHY2ClinicalTrials
LYMPHANGIOLEIOMYOMATOSISD018192Orphanet:538LYMPHANGIOLEIOMYOMATOSIS3ClinicalTrials
PEMPHIGUSD010392EFO:0004719PEMPHIGUS VULGARIS0ClinicalTrials
URINARY BLADDER NEOPLASMSD001749EFO:0000292BLADDER CARCINOMA0ClinicalTrials

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 6.3 6 195.42 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
13 3 3 14 3 2


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 0.15

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
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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