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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H50O2
Molecular Weight 454.7275
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIGMASTERYL ACETATE

SMILES

CC[C@H](\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O)C(C)C

InChI

InChIKey=IZEUIYYDWBKERE-ZRODXFKISA-N
InChI=1S/C31H50O2/c1-8-23(20(2)3)10-9-21(4)27-13-14-28-26-12-11-24-19-25(33-22(5)32)15-17-30(24,6)29(26)16-18-31(27,28)7/h9-11,20-21,23,25-29H,8,12-19H2,1-7H3/b10-9+/t21-,23-,25+,26+,27-,28+,29+,30+,31-/m1/s1

HIDE SMILES / InChI

Description

Stigmasterol acetate, a water-soluble stigmasterol derivative, possesses antagonistic properties to FXR (farnesoid X-receptor) and PXR (pregnane X receptor, NR1I2). Stigmasterol acetate has also been studied as an antibacterial agent.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Cells, transfected with retinoic X receptor (RXR), hRXR alpha , were treated with agonist or agonist plus 10 uM stigmasterol acetate (StigAc) and 24 h later harvested and processed, and luciferase activities normalized as before. The agonist ligandsused were FXR, CDCA(100 uM); pregnane X receptor (PXR), peroxisome proliferator-activated receptor gamma (PPAR gamma), rosiglitazone(1 uM). Increasing concentrations of StigAc (0–10 uM) suppress CDCA-activated FXR with an IC50 of 5–10 uM, which is well below the physiologic range of Stig levels found in the serum of patients with serological evidence of PNAC. In addition to suppressing CDCA-activated FXR-LBD activity, StigAc also suppresses ligand-activated PXR-LBD activity. Except for a slight increase in RXR alpha LBD activity, StigAc has no discernible effect on any other NRLBD tested.