garcinoic acid   Click here for help

GtoPdb Ligand ID: 10734

Synonyms: tocotrienoloic acid | trans-delta-tocotrienoloic acid
Compound class: Natural product
Comment: Garcinoic acid is a naturally occurring derivative of δ-tocotrienol, that is found in the seeds of Garcinia kola. It has been reported as a selective agonist of the pregnane X receptor [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 66.76
Molecular weight 426.28
XLogP 6.74
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES C/C(=C\CC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/CC/C=C(/C(=O)O)\C)\C
Isomeric SMILES C/C(=C\CC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/CC/C=C(/C(=O)O)\C)\C
InChI InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)/b19-9+,20-12+,21-13+/t27-/m1/s1
InChI Key QOFWRHWADNWKSU-LRXIOGKNSA-N
Bioactivity Comments
Accross a screening panel of human endocrine and metabolic nuclear receptors, including the retinoid X receptor (RXR), constitutive androstane receptor (CAR), farnesoid X receptor (FXR), vitamin D receptor (VDR), liver X receptor (LXR, α and β), and the PPARs α, δ, and γ, garcinoic acid showed a high degree of selectivity for PXR, with low off-target activity only detected at the LXRβ receptor [1].
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Pregnane X receptor Hs Agonist Agonist 6.5 pKd - 1
pKd 6.5 (Kd 3.3x10-7 M) [1]
Description: Binding affinity to hPXR ligand binding domain determined using an isothermic titration calorimetry (ITC) assay.
Pregnane X receptor Hs Agonist Agonist 5.9 pEC50 - 1
pEC50 5.9 (EC50 1.3x10-6 M) [1]
Description: Agonist activity determined using a proprietary AlphaScreen method.