Structure Database (LMSD)

Common Name
Dehydroergosterol
Systematic Name
Ergosta-5,7,9(11),22-tetraen-3β-ol
Synonyms
LM ID
LMST01031023
Formula
C28H42O
Exact Mass
Calculate m/z
394.323566
Sum Composition
ST 28:4;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Ergosterols and C24-methyl derivatives [ST0103]

Biological Context

Dehydroergosterol is a naturally occurring, fluorescent analog of cholesterol (ex/em = 324/375 nm) that mimics the properties of cholesterol in cell membranes.1 It is readily bound by cholesterol-binding proteins and has been used for real-time probing of the sterol environment and to elucidate intracellular sterol trafficking in living organisms.1

This information has been provided by Cayman Chemical

References

1. McIntosh, A.L., Atshaves, B.P., Huang, H., et al. Fluorescence techniques using dehydroergosterol to study cholesterol trafficking. Lipids 43(12), 1185-1208 (2008).

String Representations

InChiKey (Click to copy)
QSVJYFLQYMVBDR-CMNOFMQQSA-N
InChi (Click to copy)
InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1
SMILES (Click to copy)
C1[C@]2(C)C3=CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@H](C)C(C)C)CC[C@@]4([H])C3=CC=C2C[C@@H](O)C1

Other Databases

CHEBI ID
64762
PubChem CID
6436660
Cayman ID
19709

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 441.75
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 7.54
Molar Refractivity 123.97

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Updated at
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