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Ergostane information


Ergostane
Names
IUPAC name
Ergostane
Systematic IUPAC name
(1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-1-[(2R,5S)-5,6-Dimethylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number
  • 25318-39-2
  • 511-20-6 (5α)-ergostane
3D model (JSmol)
  • Interactive image
  • (5α)-ergostane: Interactive image
ChemSpider
  • 144332 (5α)-ergostane
PubChem CID
  • 6857535
  • 164641 (5α)-ergostane
UNII
  • Y0XC723P4C (5α)-ergostane checkY
CompTox Dashboard (EPA)
  • DTXSID70948162 Edit this at Wikidata
InChI
  • InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22+,23-,24+,25-,26-,27-,28+/m0/s1
    Key: WAAWMJYYKITCGF-WTPIMUJOSA-N
  • InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22?,23-,24+,25-,26-,27-,28+/m0/s1
    Key: WAAWMJYYKITCGF-ADGVWNIHSA-N
SMILES
  • C[C@H](CC[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCCC4)C)C
  • (5α)-ergostane: C[C@H](CC[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCCC4)C)C
Properties
Chemical formula
C28H50
Molar mass 386.708 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses;[citation needed] however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides.[1][2] However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.[3]

  1. ^ Glotter, E. (1991). "Withanolides and related ergostane-type steroids". Natural Product Reports. 8 (4): 415–40. doi:10.1039/np9910800415. ISSN 0265-0568. PMID 1787922.
  2. ^ Kirson, Isaac; Glotter, Erwin (1981). "Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review". Journal of Natural Products. 44 (6): 633–647. doi:10.1021/np50018a001. ISSN 0163-3864.
  3. ^ Brocks, Jochen J.; Jarrett, Amber J. M.; Sirantoine, Eva; Hallmann, Christian; Hoshino, Yosuke; Liyanage, Tharika (2017). "The rise of algae in Cryogenian oceans and the emergence of animals". Nature. 548 (7669): 578–581. Bibcode:2017Natur.548..578B. doi:10.1038/nature23457. PMID 28813409. S2CID 205258987.

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Ergostane

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Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses;[citation needed] however various functionalized...

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Withaferin A

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family Solanaceae. It is the first member of the withanolide class of ergostane type product to be discovered. Withanolides are a group of naturally occurring...

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Withanolide

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are a group of at least 300 naturally occurring steroids built on an ergostane skeleton. They occur as secondary metabolites primarily in genera of the...

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Agaricus subrufescens

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upper side, and covered with cottony scales on the lower side. A type of ergostane-type compounds called blazeispirols have been isolated from A. subrufescens...

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This is a list of neurosteroids, or natural and synthetic steroids that are active on the mammalian nervous system through receptors other than steroid...

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Anicequol

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(developmental code names NGA0187, NGD-187) is a naturally occurring ergostane steroid produced by Acremonium sp. TF-0356 which has nerve growth factor-like...

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Stigmastane

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24R-ethylcholestane is a tetracyclic triterpene, along with cholestane and ergostane, this sterane is used as a biomarker for early eukaryotes. 5α-Stigmastane...

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Polyporus umbellatus

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1055/s-0030-1249926. PMID 20458671. Sun Y, Yasukawa K (2008). "New anti-inflammatory ergostane-type ecdysteroids from the sclerotium of Polyporus umbellatus". Bioorg...

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Poriferastane

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Stigmastane (24R-ethylcholestane) Campestane (24R-methylcholestane) Ergostane (24S-methylcholestane) International Union of Pure and Applied Chemistry...

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C28H50

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exact mass: 386.3913 u) may refer to: Campestane (24R-methylcholestane) Ergostane (24S-methylcholestane) This set index page lists chemical structure articles...

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Campestane

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isolated from the rapeseed (Brassica campestris), hence the name. Cholestane Ergostane (24S-methylcholestane) Campestanol (Campestan-3β-ol) International Union...

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Ramalina peruviana

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hopane-6α,22-diol, hopane-22-ol, hopane-6α,16β,22-triol, along with two ergostane-type sterols, 5α,8α-ergosterol peroxide, and brassicasterol. Three new...

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Astraeus hygrometricus

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mycelia grown in liquid culture. The compound has a polyhydroxylated ergostane-type nucleus. Ethanol extracts of the fruit body are high in antioxidant...

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Cholane

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steroids and bile acids (e.g. cholic acid). 5α-Cholane 5β-Cholane Cholestane Ergostane International Union of Pure and Applied Chemistry (2014). Nomenclature...

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Ergosterol peroxide

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PMID 2813575. Tchouankeu JC, Nyasse B, Tsamo E, Sondengam B, Morin C (1992). "An ergostane derivative from the bark of Entandrophragma utile". Phytochemistry. 31...

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Tapinella atrotomentosa

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February 2024 (link) Vokáč K, Buděšínský M, Harmatha J, Píš J (1998). "New ergostane type ecdysteroids from fungi. Ecdysteroid constituents of mushroom Paxillus...

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