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4β-hydroxy Cholesterol

CAT: 0013-GTR19224570-04Size: 25 mgDry Ice: NoHazardous: No
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Description
4β-Hydroxycholesterol (CAS 17320-10-4) is a valuable oxysterol used in life science research. It serves as a biomarker for CYP3A4/5 enzyme activity and is employed in studies of cholesterol metabolism, neurodegenerative diseases, and drug interactions in both in vitro and in vivo models.
CAS Number
17320-10-4
Field of Research
Metabolism Research
Smiles
CC (C) CCC[C@@H] (C) [C@H]1CCC2C3CC=C4[C@@H] (O) [C@@H] (O) CC[C@]4 (C) C3CC[C@]12C
Molecular Weight
402.653
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

4beta-Hydroxycholesterol

4beta-hydroxycholesterol is a oxysterol that is cholesterol in which the hydrogen at the 4beta position has been replaced by a hydroxy group. A metabolite of cholesterol formed by the drug-metabolizing enzyme cytochrome P450 3A4, it is one of the major oxysterols in the human circulation. It has a role as a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a diol, a 3beta-sterol and an oxysterol. It is functionally related to a cholesterol.

CAS Number17320-10-4
PubChem CID3247060
IUPAC Name(3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
Molecular FormulaC27H46O2
Molecular Weight402.7
XLogP7.4
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity624
SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H]([C@@H]4O)O)C)C
InChI
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChIKey
CZDKQKOAHAICSF-JSAMMMMSSA-N
Chemical Structure
2D Structure
2D structure of 4beta-Hydroxycholesterol
CAS: 17320-10-4
CID: 3247060
Formula: C27H46O2
MW: 402.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.7
XLogP37.4
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
Complexity624
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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