temsirolimus   Click here for help

GtoPdb Ligand ID: 5892

Synonyms: CCI-779 | Torisel®
Approved drug
temsirolimus is an approved drug (FDA & EMA (2007))
Compound class: Synthetic organic
Comment: Temsirolimus is a Type-3 kinase inhibitor and was first approved by the FDA in 2007. There is some ambiguity in the literature surrounding the exact stereochemistry of temsirolimus. Other common representations are CID 23724530, CID 24847874 and CID 9876533. Our representation and the PubChem and ChEMBL links in the table above show a structure identical to that contained in the INN record for this drug.
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View more information in the IUPHAR Pharmacology Education Project: temsirolimus

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 17
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 241.96
Molecular weight 1029.6
XLogP 3.54
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC1CC(CCC1OC(=O)C(CO)(CO)C)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]1OC(=O)C(CO)(CO)C)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/C56H87NO16/c1-33-17-13-12-14-18-34(2)45(68-9)29-41-22-20-39(7)56(67,73-41)51(63)52(64)57-24-16-15-19-42(57)53(65)71-46(30-43(60)35(3)26-38(6)49(62)50(70-11)48(61)37(5)25-33)36(4)27-40-21-23-44(47(28-40)69-10)72-54(66)55(8,31-58)32-59/h12-14,17-18,26,33,35-37,39-42,44-47,49-50,58-59,62,67H,15-16,19-25,27-32H2,1-11H3/b14-12+,17-13+,34-18+,38-26+/t33-,35-,36-,37-,39-,40+,41+,42+,44-,45+,46+,47-,49-,50+,56-/m1/s1
InChI Key CBPNZQVSJQDFBE-FUXHJELOSA-N
References
1. Kong F, Zhu T, Yu K, Pagano TG, Desai P, Radebaugh G, Fawzi M. (2011)
Isolation and structure of homotemsirolimuses A, B, and C.
J Nat Prod, 74 (4): 547-53. [PMID:21438579]