toddacoumalone   Click here for help

GtoPdb Ligand ID: 13467

Synonyms: compound 8 [PMID: 24597921]
Immunopharmacology Ligand
Compound class: Natural product
Comment: Toddacoumalone is one of a number of coumarin type compounds identified in extracts from the roots of the African Zanthoxylum (Toddalia) asiatica climbing plant. The plant is used medicinally by many African peoples. Experimental analysis demonstrates that toddacoumalone inhibits phosphodiesterase 4 (PDE4) enzymatic activity [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 74.3
Molecular weight 513.58
XLogP 4.15
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 CC(=C[C@@H]1C[C@](C)(/C=C/C2=C(C=C(C3=C2OC(=O)C=C3)OC)OC)OC4=C1C(=O)N(C)C5=C4C=CC=C5)C
Isomeric SMILES COC1=CC(OC)=C(/C=C/[C@@]2(C)C[C@@H](C=C(C)C)C3=C(O2)C4=CC=CC=C4N(C)C3=O)C5=C1C=CC(=O)O5
InChI InChI=1S/C31H31NO6/c1-18(2)15-19-17-31(3,38-29-20-9-7-8-10-23(20)32(4)30(34)27(19)29)14-13-22-25(36-6)16-24(35-5)21-11-12-26(33)37-28(21)22/h7-16,19H,17H2,1-6H3/b14-13+/t19-,31+/m1/s1
InChI Key IOVBMEHJQSKXAU-CSLHTZHMSA-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 Natural product
IUPAC Name Click here for help
(2R,4S)-2-[(E)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-2,6-dimethyl-4-(2-methylprop-1-enyl)-3,4-dihydropyrano[3,2-c]quinolin-5-one
Synonyms Click here for help
compound 8 [PMID: 24597921]
Database Links Click here for help
BindingDB Ligand 50603817
CAS Registry No. 139750-79-1 (source: PubChem)
ChEMBL Ligand CHEMBL5170835
GtoPdb PubChem SID 500839877
PubChem CID 86302487
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