Structure Database (LMSD)

Common Name
25-hydroxy-5,6alpha-epoxycholesterol
Systematic Name
5α,6α-epoxycholestan-3β,25-diol
Synonyms
  • 25-hydroxy-5alpha,6alph-epoxycholestan-3beta-ol
LM ID
LMST01010584
Formula
C27H46O3
Exact Mass
Calculate m/z
418.344695
Sum Composition
ST 27:1;O3
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

References

Comments
Submitted by Marc Poirot

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
27-hydroxylation of oncosterone by CYP27A1 switches its activity from pro-tumor to anti-tumor,
J Lipid Res, 2023
Pubmed ID: 37981011

String Representations

InChiKey (Click to copy)
CWPADSOWYAHELV-QXQVGDIMSA-N
InChi (Click to copy)
InChI=1S/C27H46O3/c1-17(7-6-12-24(2,3)29)20-8-9-21-19-15-23-27(30-23)16-18(28)10-14-26(27,5)22(19)11-13-25(20,21)4/h17-23,28-29H,6-16H2,1-5H3/t17-,18+,19+,20-,21+,22+,23+,25-,26-,27+/m1/s1
SMILES (Click to copy)
[C@]12(C[C@@H]3O[C@]43C[C@@H](O)CC[C@]4(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(O)(C)C)CC[C@@]21[H])[H]

Other Databases

PubChem CID
171117795

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 5
Aromatic Rings
Rotatable Bonds 5
Van der Waals Molecular Volume 440.23
Topological Polar Surface Area 52.99
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.86
Molar Refractivity 122.08

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Created at
31st Aug 2023
Updated at
31st Aug 2023