Structure Database (LMSD)

Common Name
25-Hydroxy-7-oxocholesterol
Systematic Name
3β,25-Dihydroxycholest-5-en-7-one
Synonyms
  • 25-hydroxy 7-keto cholesterol
LM ID
LMST01010449
Formula
C27H44O3
Exact Mass
Calculate m/z
416.329046
Sum Composition
ST 27:2;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

7-keto-25-hydroxy Cholesterol is an oxysterol and a proposed metabolite of 7-keto cholesterol and 7-dehydro cholesterol .1 It binds to and activates Smoothened (Smo) at the conserved extracellular cysteine-rich domain (CRD) in a reporter assay. It also increases EGF high affinity binding site numbers in normal rat kidney (NRK) cells.2

This information has been provided by Cayman Chemical

References

1. Myers, B.R., Sever, N., Chong, Y.C., et al. Hedgehog pathway modulation by multiple lipid binding sites on the smoothened effector of signal response. Dev. Cell. 26(4), 346-357 (2013).
2. Astruc, M.E., and Lahoua, Z. Potentiation by cholesterol and vitamin D3 oxygenated derivatives of arachidonic acid release and prostaglandin E2 synthesis induced by the epidermal growth factor in NRK 49F cells: The role of protein kinase C. Cell Signal. 6(7), 763-775 (1994).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Bile acid biosynthesis in Smith-Lemli-Opitz syndrome bypassing cholesterol: Potential importance of pathway intermediates.,
J Steroid Biochem Mol Biol, 2020
Pubmed ID: 33246156

String Representations

InChiKey (Click to copy)
NQBVGGWSAXBLBE-BYJKJZODSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@]12(C(=O)C=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(O)(C)C)CC[C@@]21[H])[H]

Other Databases

CHEBI ID
180497
PubChem CID
10319758
Cayman ID
25973

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 447.31
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.26
Molar Refractivity 121.93

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Created at
4th Jan 2021
Updated at
4th Jan 2021