resiniferatoxin   Click here for help

GtoPdb Ligand ID: 2491

Abbreviated name: RTX
PDB Ligand
Comment: Resiniferatoxin, an extract from resin spurge (Euphorbia resinifera), is a TRPV1 agonist.
There is some ambiguity online and in the literature as to the exact stereochemistry of resiniferatoxin. The representation shown here matches that in the PubChem and ChEMBL links above, while several tautomers and stereoisomers are also listed on PubChem, and ChEBI represents the compound with the entry CHEBI:8809.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 120.75
Molecular weight 628.27
XLogP 2.85
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(ccc1O)CC(=O)OCC1=CC2C3OC4(OC2(C2C(C1)(O)C(=O)C(=C2)C)C(CC3(O4)C(=C)C)C)Cc1ccccc1
Isomeric SMILES COc1cc(ccc1O)CC(=O)OCC1=C[C@H]2[C@H]3O[C@]4(O[C@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)[C@@H](C[C@@]3(O4)C(=C)C)C)Cc1ccccc1
InChI InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35-,36-,37-/m1/s1
InChI Key DSDNAKHZNJAGHN-MXTYGGKSSA-N
Classification Click here for help
Compound class Natural product or derivative
Database Links Click here for help
BindingDB Ligand 20285
CAS Registry No. 57444-62-9 (source: Scifinder)
ChEMBL Ligand CHEMBL17976
GtoPdb PubChem SID 53801085
PubChem CID 5702546
RCSB PDB Ligand 6EU
Search Google for chemical match using the InChIKey DSDNAKHZNJAGHN-MXTYGGKSSA-N
Search Google for chemicals with the same backbone DSDNAKHZNJAGHN
Search UniChem for chemical match using the InChIKey DSDNAKHZNJAGHN-MXTYGGKSSA-N
Search UniChem for chemicals with the same backbone DSDNAKHZNJAGHN
Wikipedia Resiniferatoxin