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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL269732
CHEMBL269732
Compound Name TACROLIMUS
ChEMBL Synonyms FK-506 | Prograf | Tacrolimus Hydrate | Tacrolimus | FR-900506 | Protopic
Max Phase 4 (Approved)
Trade Names Prograf | Protopic | Tacrolimus
Molecular Formula C44H69NO12

Additional synonyms for CHEMBL269732 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)\[C@H]2OC(=O)[C@@H]3CCCCN ...
Download SMILES
Standard InChI InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)4 ...
Download InChI
Standard InChI Key QJJXYPPXXYFBGM-LFZNUXCKSA-N

Mechanism of Action

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

Indications for CHEMBL269732

MESH Heading MESH ID EFO ID EFO Term Max phase for indication
COLITIS, ULCERATIVED003093EFO:0000729ULCERATIVE COLITIS4
CROHN DISEASED003424EFO:0000384CROHN'S DISEASE2
DERMATITIS, ATOPICD003876EFO:0000274ATOPIC ECZEMA4
DERMATITIS, SEBORRHEICD012628HP:0001051SEBORRHEIC DERMATITIS4
DIABETES MELLITUSD003920EFO:0000400DIABETES MELLITUS4
ECZEMAD004485HP:0000964ECZEMA4
EYE DISEASESD005128EFO:0003966EYE DISEASE2
GLOMERULONEPHRITIS, IGAD005922EFO:0004194IGA GLOMERULONEPHRITIS2
GRAFT VS HOST DISEASED006086EFO:0004599ACUTE GRAFT VS. HOST DISEASE4
HEPATITIS CD006526EFO:0003047HEPATITIS C INFECTION4
HYPERTENSION, PULMONARYD006976EFO:0001361PULMONARY HYPERTENSION2
KIDNEY DISEASESD007674EFO:0003086KIDNEY DISEASE3
LIVER DISEASESD008107EFO:0001421LIVER DISEASE2
LUPUS ERYTHEMATOSUS, SYSTEMICD008180EFO:0002690SYSTEMIC LUPUS ERYTHEMATOSUS4
MYASTHENIA GRAVISD009157EFO:0004991MYASTHENIA GRAVIS3
NEPHROTIC SYNDROMED009404EFO:0004255NEPHROTIC SYNDROME4

Molecule Features

CHEMBL269732 compound icon
Drug Type:Natural Product Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

There are 7 structural alerts for CHEMBL269732. To view alerts please click here.

Alternate Forms of Compound in ChEMBL


CHEMBL269732

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
804 803.482 4.83 7 178.36 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
12 3 2 13 3 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.97 - 4.79 4.78 0 57 0.18

Compound Cross References

ATC D - DERMATOLOGICALS
D11 - OTHER DERMATOLOGICAL PREPARATIONS
D11A - OTHER DERMATOLOGICAL PREPARATIONS
D11AH - Agents for dermatitis, excluding corticosteroids
D11AH01 - tacrolimus

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AD - Calcineurin inhibitors
L04AD02 - tacrolimus

ChemSpider ChemSpider:QJJXYPPXXYFBGM-LFZNUXCKSA-N
DailyMed tacrolimus
PubChem SID: 144205609 SID: 50111459

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL269732



ACToR 104987-11-3
Atlas tacrolimus
BindingDB 50030448
ChEBI 61049
DrugBank DB00864
eMolecules 26941752
FDA SRS Y5L2157C4J
Guide to Pharmacology 6784
Human Metabolome Database HMDB15002
KEGG Ligand C01375
LINCS LSM-43009
MolPort MolPort-003-666-518 MolPort-027-950-906
Nikkaji J313.679E
PDBe FK5
PubChem 445643
PubChem: Drugs of the Future 12013904
PubChem: Thomson Pharma 14889261 14815954
Selleck FK-506-(Tacrolimus)
SureChEMBL SCHEMBL3088

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