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20 (S) -Hydroxycholesterol

CAT: 0013-GTR19244415-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19244415-01Size:500 mg
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Description
20 (S) -Hydroxycholesterol (Standard) is the analytical standard of 20 (S) -Hydroxycholesterol. This product is intended for research and analytical applications. 20 (S) -hydroxyCholesterol (20α-Hydroxycholesterol) is an allosteric activator of the oncoprotein smoothened (Smo) that activates the hedgehog (Hh) signaling pathway with an EC50 of 3 μM in a gene transcription reporter assay using NIH3T3 cells.
CAS Number
516-72-3
Purity
>98% (HPLC)
Smiles
C[C@@]12[C@] ([C@]3 ([C@@] ([C@]4 (C) C (=CC3) C[C@@H] (O) CC4) (CC1) [H]) [H]) (CC[C@@]2 ([C@@] (CCCC (C) C) (C) O) [H]) [H]
Molecular Formula
C27H46O2
Molecular Weight
402.65
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

20alpha-Hydroxycholesterol

20-hydroxycholesterol is an oxysterol that is cholesterol substituted by a hydroxy group at position 20. It has a role as a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-hydroxy steroid and an oxysterol.

CAS Number516-72-3
PubChem CID121935
IUPAC Name(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Molecular FormulaC27H46O2
Molecular Weight402.7
XLogP6.9
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity638
SMILES
CC(C)CCC[C@@](C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O
InChI
InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChIKey
MCKLJFJEQRYRQT-APGJSSKUSA-N
Chemical Structure
2D Structure
2D structure of 20alpha-Hydroxycholesterol
CAS: 516-72-3
CID: 121935
Formula: C27H46O2
MW: 402.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.7
XLogP36.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass402.349780706
Monoisotopic Mass402.349780706
Topological Polar Surface Area40.5 Ų
Heavy Atom Count29
Formal Charge0
Complexity638
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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