Structure Database (LMSD)

Common Name
27-hydroxy-5,6beta-epoxycholesterol
Systematic Name
5β,6β-epoxycholestan-3β,27-diol
Synonyms
  • 27-hydroxy-5beta,6beta-epoxycholestan-3beta-ol
LM ID
LMST01010586
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
Homo sapiens (#9606)
Mammalia (#40674)
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)
ISPPNARJZMPPNB-VQHYWWHISA-N
InChi (Click to copy)
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-20-14-24-27(30-24)15-19(29)10-13-26(27,4)23(20)11-12-25(21,22)3/h17-24,28-29H,5-16H2,1-4H3/t17?,18-,19+,20+,21-,22+,23+,24-,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(C)CO)CC[C@@]21[H])[H]

Other Databases

PubChem CID
171117797

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 5
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 440.23
Topological Polar Surface Area 52.99
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.72
Molar Refractivity 122.01

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