LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Ergosterol

Systematic Name

ergosta-5,7,22E-trien-3β-ol

Synonyms

LM ID

LMST01030093

Formula

C₂₈H₄₄O

Exact Mass

Calculate m/z

396.339215

Sum Composition

ST 28:3;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View BMRB ID(NMR) spectrum

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Ergosterol is a sterol that is found predominantly in membranes of fungi. It is converted into vitamin D2 by ultraviolet light.¹ Ergosterol and its biosynthetic pathway are significant targets for some fungicides.^2,3,4

This information has been provided by Cayman Chemical

References

1. Bikle, D.D. Vitamin D metabolism, mechanism of action, and clinical applications. Chem. Biol. 21(3), 319-329 (2014).

2. Carillo-Muñoz, A.J., Giusiano, G., Ezkurra, P.A., et al. Antifungal agents: mode of action in yeast cells. Rev.Esp.Quimioter. 19(2), 130-139 (2006).

3. Fromtling, R.A. Overview of medically important antifungal azole derivatives. Clin. Microbiol. Rev. 1(2), 187-217 (1988).

4. Ogita, A., Fujita, K.i., and Tanaka, T. Enhancing effects on vacuole-targeting fungicidal activity of amphotericin B. Front. Microbiol. 3, 100 (2012).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

String Representations

InChiKey (Click to copy)

DNVPQKQSNYMLRS-APGDWVJJSA-N

InChi (Click to copy)

InChI=1S/C28H44O/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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])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