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7α-Hydroxy-4-cholesten-3-one

CAT: 0804-HY-113259-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-113259-01Size:1 mg
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Description
7α-Hydroxy-4-cholesten-3-one is an intermediate in synthesis of bile acids from cholesterol. 7α-Hydroxy-4-cholesten-3-one is a pregnane X receptor (PXR) agonist. 7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. 7α-Hydroxy-cholest-4-en-3-one is the physiological substrate for CYP8B1[1][2].
CAS Number
3862-25-7
UNSPSC
12352211
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/7α-hydroxy-4-cholesten-3-one.html
Purity
99.60
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
Molecular Formula
C27H44O2
Molecular Weight
400.64
References & Citations
[1]Offei SD, et al. Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption. Steroids. 2019 Nov;151:108449.|[2] Gälman C, et al. Bile acid synthesis in humans has a rapid diurnal variation that is asynchronous with cholesterol synthesis. Gastroenterology. 2005 Nov;129 (5) :1445-53.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

7alpha-Hydroxy-4-cholesten-3-one

7alpha-hydroxycholest-4-en-3-one is a cholestanoid consisting of a cholesterol core having an oxo group at the 3-position, a C=C bond at the 4,5-position and an alpha-hydroxy group at the 7-position. It has a role as a mouse metabolite and a human metabolite. It is a 7alpha-hydroxy steroid, a 3-oxo-Delta(4) steroid and a cholestanoid.

CAS Number3862-25-7
PubChem CID123743
IUPAC Name(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Molecular FormulaC27H44O2
Molecular Weight400.6
XLogP7.3
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity663
SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](CC4=CC(=O)CC[C@]34C)O)C
InChI
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChIKey
IOIZWEJGGCZDOL-RQDYSCIWSA-N
Chemical Structure
2D Structure
2D structure of 7alpha-Hydroxy-4-cholesten-3-one
CAS: 3862-25-7
CID: 123743
Formula: C27H44O2
MW: 400.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight400.6
XLogP37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass400.334130642
Monoisotopic Mass400.334130642
Topological Polar Surface Area37.3 Ų
Heavy Atom Count29
Formal Charge0
Complexity663
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
T10196-017α-Hydroxy-4-cholesten-3-one
sc-2106567β-Hydroxy-4-cholesten-3-one
FH58232-017-Hydroxy-4-cholesten-3-one-D7
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sc-2174787β-Hydroxy-4-cholesten-3-one-d7
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BUP00441-017a-Hydroxy-4-cholesten-3-one
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