Structure Database (LMSD)
Common Name
3,5-cholestadien-7-one
Systematic Name
cholesta-3,5-dien-7-one
Synonyms
- 7-keto-3,5-cholestadiene
3D model of 3,5-cholestadien-7-one
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Cholesta-3,5-dien-7-one is an oxysterol and a negative allosteric modulator of GABAA receptors.1,2 It reduces GABA-induced currents in HEK cells expressing α1β1γ2 or α4β3γ2 subunit-containing GABAA receptors (IC50s = 1.5 and 1 µM, respectively).2 Cholesta-3,5-dien-7-one (500 nM) reduces GABA-induced depolarization of peptidergic and non-peptidergic nociceptors, C-LTMRs, and cold thermosensors in isolated mouse dorsal root ganglion (DRG) neurons. In vivo, cholesta-3,5-dien-7-one (2, 10, and 50 mg/kg) increases latency to nocifensive behaviors in the hot plate test in mice.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
TTXJJFWWNDJDNR-CZRUWHASSA-N
InChi (Click to copy)
InChI=1S/C27H42O/c1-18(2)9-8-10-19(3)21-12-13-22-25-23(14-16-27(21,22)5)26(4)15-7-6-11-20(26)17-24(25)28/h6,11,17-19,21-23,25H,7-10,12-16H2,1-5H3/t19-,21-,22+,23+,25+,26+,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])[C@]3([H])C(=O)C=C2C=CC1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
427.09
Topological Polar Surface Area
17.07
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
1
logP
7.37
Molar Refractivity
117.96
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Created at
-
Updated at
16th Jan 2024