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7-keto-25-Hydroxycholesterol

CAT: 0804-HY-133974Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-133974Size:1 mg
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Description
7-keto-25-Hydroxycholesterol (7-keto-25-OHC), a oxysterol, is a Smoothened (Smo) activator. 7-keto-25-Hydroxycholesterol binds to the extracellular cysteine-rich domain (CRD) of Smo[1].
CAS Number
64907-23-9
Product Name Alternative
7-keto-25-OHC
UNSPSC
12352211
Target
Smo
Type
Reference compound
Related Pathways
Stem Cell/Wnt
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/7-keto-25-hydroxycholesterol.html
Smiles
CC(C)(O)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])C(C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
Molecular Formula
C27H44O3
Molecular Weight
416.64
References & Citations
[1]Benjamin R Myers, et al. Hedgehog pathway modulation by multiple lipid binding sites on the smoothened effector of signal response. Dev Cell. 2013 Aug 26;26 (4) :346-57.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

(3beta)-3,25-Dihydroxycholest-5-en-7-one

7-keto-25-hydroxycholesterol is a 3beta-hydroxy-Delta(5)-steroid, a 3beta-sterol, a 7-oxo steroid, a cholestanoid and an oxysterol.

CAS Number64907-23-9
PubChem CID10319758
IUPAC Name(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
Molecular FormulaC27H44O3
Molecular Weight416.6
XLogP5.7
Topological Polar Surface Area57.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Heavy Atom Count30
Formal Charge0
Complexity709
SMILES
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CC[C@@H](C4)O)C)C
InChI
InChI=1S/C27H44O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-22,24,28,30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,24+,26+,27-/m1/s1
InChIKey
NQBVGGWSAXBLBE-BYJKJZODSA-N
Chemical Structure
2D Structure
2D structure of (3beta)-3,25-Dihydroxycholest-5-en-7-one
CAS: 64907-23-9
CID: 10319758
Formula: C27H44O3
MW: 416.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight416.6
XLogP35.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass416.32904526
Monoisotopic Mass416.32904526
Topological Polar Surface Area57.5 Ų
Heavy Atom Count30
Formal Charge0
Complexity709
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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