sirolimus   

GtoPdb Ligand ID: 6031

Synonyms: AY-22989 | Rapamune® | rapamycin | WY-090217
sirolimus is an approved drug (FDA (1999), EMA (2001))
Compound class: Synthetic organic
Comment: Sirolimus is a macrolide produced by the bacteria Streptomyces hygroscopicus. It has potent immunosuppressive and antiproliferative properties.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 195.43
Molecular weight 913.56
XLogP 4.32
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COC1CC(CCC1O)CC(C1OC(=O)C2CCCCN2C(=O)C(=O)C2(O)OC(CCC2C)CC(OC)C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)C1)C)C)O)OC)C)C)C)C
Isomeric SMILES CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@H]([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H](CC[C@H]2C)C[C@H](OC)/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C1)C)/C)O)OC)C)C)/C)C
InChI InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
InChI Key QFJCIRLUMZQUOT-HPLJOQBZSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1999), EMA (2001))
International Nonproprietary Names
INN number INN
7104 sirolimus
Synonyms
AY-22989 | Rapamune® | rapamycin | WY-090217
Database Links
CAS Registry No. 53123-88-9
ChEBI CHEBI:9168
ChEMBL Ligand CHEMBL413
DrugBank Ligand DB00877
DrugCentral Ligand 2446
GtoPdb PubChem SID 178102653
Immunopaedia Search sirolimus
PubChem CID 5284616
RCSB PDB Ligand RAP
Search Google for chemical match using the InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
Search Google for chemicals with the same backbone QFJCIRLUMZQUOT
Search PubMed clinical trials sirolimus
Search PubMed titles sirolimus
Search PubMed titles/abstracts sirolimus
Search UniChem for chemical match using the InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
Search UniChem for chemicals with the same backbone QFJCIRLUMZQUOT
SynPHARM 80549 (in complex with FK506 binding protein 1A)
Wikipedia Sirolimus

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Tocris
Rapamycin
Cat. No. 1292