pristimerin   Click here for help

GtoPdb Ligand ID: 13530

Synonyms: celastrol methyl ester
Compound class: Synthetic organic
Comment: Pristimerin is a naturally ocurring terpenoid compound that has been isolated from the seeds of the plant Celastrus paniculatus. It has been attributed with multiple biological activities, and is the subject of medicinal chemistry efforts to produce bioactive synthetic derivatives with therapeutic potential [2]. Molecular targets and mechanism of action are yet to be fully determined.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 63.6
Molecular weight 464.64
XLogP 8.3
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CC1=C(C(=O)C=C2C1=CC=C3[C@@]2(C)CC[C@@]4(C)[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(=O)OC)O
Isomeric SMILES CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)OC)C)C)C)C)O
InChI InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1
InChI Key JFACETXYABVHFD-WXPPGMDDSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
methyl (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate
Synonyms Click here for help
celastrol methyl ester
Database Links Click here for help
BindingDB Ligand 50481947
ChEBI CHEBI:8416
ChEMBL Ligand CHEMBL54804
DrugBank Ligand DB17049
GtoPdb PubChem SID 500839940
PubChem CID 159516
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UniChem Compound Search for chemical match using the InChIKey JFACETXYABVHFD-WXPPGMDDSA-N
UniChem Connectivity Search for chemical match using the InChIKey JFACETXYABVHFD-WXPPGMDDSA-N