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25-Hydroxycholesterol (Standard)

CAT: 0804-HY-113134R-02Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-113134R-02Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
25-Hydroxycholesterol (Standard) is the analytical standard of 25-Hydroxycholesterol. This product is intended for research and analytical applications. 25-Hydroxycholesterol (25-OHC) is a metabolite of cholesterol that is produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells.
CAS Number
2140-46-7
UNSPSC
12352100
Target
Endogenous Metabolite; Reference Standards
Related Pathways
Metabolic Enzyme/Protease; Others
Field of Research
Inflammation/Immunology
Smiles
CC(C)(O)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Molecular Formula
C27H46O2
Molecular Weight
402.65
References & Citations
[1]McDonald JG, et al. Editorial: 25-Hydroxycholesterol: a new life in immunology. J Leukoc Biol. 2010 Dec;88 (6) :1071-2.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

25-Hydroxycholesterol

25-hydroxycholesterol is a 25-hydroxy steroid and an oxysterol. It has a role as a human metabolite. It is functionally related to a cholesterol.

CAS Number2140-46-7
PubChem CID65094
IUPAC Name(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-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
XLogP6.8
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity636
SMILES
C[C@H](CCCC(C)(C)O)[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
InChI
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChIKey
INBGSXNNRGWLJU-ZHHJOTBYSA-N
Chemical Structure
2D Structure
2D structure of 25-Hydroxycholesterol
CAS: 2140-46-7
CID: 65094
Formula: C27H46O2
MW: 402.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.7
XLogP36.8
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
Complexity636
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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