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25-Hydroxycholesterol

CAT: 0931-T4717-04Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0931-T4717-04Size:50 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
2140-46-7
Target
HMG-CoA Reductase, Endogenous Metabolite
Related Pathways
Metabolism
Purity
0.9989
Bioactivity
25-Hydroxycholesterol is a steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs) . It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells.
Smiles
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Molecular Formula
C27H46O2
Molecular Weight
402.65
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

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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Alternative Products

CatalogName
BUP06234-0125-Hydroxycholesterol
HY-113134R-0125-Hydroxycholesterol (Standard)
HY-N15915Ent-25-Hydroxycholesterol
HY-113134S25-Hydroxycholesterol-d6
GTR10399457Mouse 25-hydroxycholesterol
GTR10419253Rabbit 25-hydroxycholesterol
GTR10437159Canine 25-hydroxycholesterol
GTR10396720Goat 25-hydroxycholesterol

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