γ-sitosterol (Q27262523)

(3S)-17-[(5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

inferred from SMILES

1 reference

inferred from SMILES

mass

414.386±0 dalton

1 reference

Clionasterol (English)

(3S,8S,9S,10R,13R,14R,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

14 October 2016

stereoisomer of

2 references

(3S,8R,9R,10R,13R,14R,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

2 references

(3R,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

2 references

(3S,8S,9S,10R,13R,14S,17S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8S,9S,10R,13R,14S,17R)-17-[(2S,5S)-5-Ethyl-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8R,9S,10S,13R,14S,17S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8R,9S,10R,13R,14R,17S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8S,9S,10R,13R,14S,17R)-17-[(2S,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8S,9S,10R,13R,14S,17S)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8R,9R,10R,13R,14R,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8R,9S,10R,13R,14R,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3R,8R,9R,10S,13R,14R,17S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

(3S,8S,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

1 reference

1 reference

1 reference

C₂₉H₅₀O

1 reference

Clionasterol (English)

14 October 2016

canonical SMILES

CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C

1 reference

Clionasterol (English)

14 October 2016

isomeric SMILES

CC[C@@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Clionasterol (English)

14 October 2016

1 reference

Ellisella paraplexauroides

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Eunicella labiata

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia ruberrima

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia viminalis

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia violetta

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Cinachyrella alloclada

1 reference

Sterol composition of three marine sponge species from the genus Cinachyrella

Cinachyrella schulzei

1 reference

Sterol composition of three marine sponge species from the genus Cinachyrella

Acorus calamus

1 reference

Identification of an EcoRI restriction site for a rapid and precise determination of beta-asarone-free Acorus calamus cytotypes

Petrosia durissima

1 reference

Two new acetylenic derivatives and a new meroditerpenoid from a Taiwanese marine sponge Strongylophora durissima

Achillea santolina

1 reference

Further constituents of Achillea ageratum

Boodleopsis pusilla

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Bryopsis plumosa

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Senna siamea

2 references

Cassiadinine, a chromone alkaloid and (+)-6-hydroxy-mellein, a dihydroisocoumarin from Cassia siamea

Cassiadinine, a chromone alkaloid and (+)-6-hydroxy-mellein, a dihydroisocoumarin from Cassia siamea

Caulerpa racemosa

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Caulerpa taxifolia

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Cladophora rupestris

1 reference

Occurrence of steryl glycosides and acylated steryl glycosides in some marine algae

Cladophora vagabunda

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Codium decorticatum

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Enteromorpha clathrata

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Euphorbia helioscopia

1 reference

Euphorbia helioscopia L.

Gracilaria edulis

2 references

Dihydroxysterols from the marine red alga, Gracilaria edulis

Minor C29-steroids from the marine red alga, Gracilaria edulis

Kigelia africana

1 reference

γ-Sitosterol, a cytotoxic sterol from Markhamia zanzibarica and Kigelia africana

Markhamia zanzibarica

1 reference

γ-Sitosterol, a cytotoxic sterol from Markhamia zanzibarica and Kigelia africana

Pavlova gyrans

1 reference

Free and combined sterols ofPavlova gyrans

Petrosia weinbergi

2 references

Sterols of the marine sponge Petrosia weinbergi: implications for the absolute configurations of the antiviral orthoesterols and weinbersterols

Sterols of the marine sponge Petrosia weinbergi: implications for the absolute configurations of the antiviral orthoesterols and weinbersterols

Peucedanum decumbens

1 reference

Chemical constituents of Peucedanum japonicum roots

Porphyridium

1 reference

Occurrence of steryl glycosides and acylated steryl glycosides in some marine algae

Spheciospongia inconstans

2 references

Studies on Marine Chemicals, Part IV. Isolation of Cholesterol Derivatives from the Marine Sponge Spirastrella inconstans

Studies on Marine Chemicals, Part VI. A New Clionasterol Derivative from the Marine Sponge Spirastrella inconstans

Lessertia frutescens

1 reference

In vitro culture studies of Sutherlandia frutescens on human tumor cell lines

mealworm beetle

1 reference

Migration of the C-25 hydrogen of clionasterol to the C-24 position during dealkylation by the insect, Tenebrio molitor

Thalia multiflora

1 reference

Antitubercular sterols from Thalia multiflora Horkel ex Koernicke

Trifolium repens

1 reference

A dihydroxycyclopentadienone and other constituents from the seeds of Trifolium repens

Udotea petiolata

1 reference

Udoteal B, A New Linear Diterpenoid from the Green AlgaUdotea petiolata

Ulva fasciata

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Sea lettuce

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Vernonia incana

1 reference

Glaucolides and related sesquiterpene lactones from Vernonia incana

Anaxagorea crassipetala

1 reference

Neolignans from Anaxagorea clavata

Aria edulis

1 reference

Minor C29-steroids from the marine red alga, Gracilaria edulis

Artocarpus kemando

1 reference

Artomandin, a new xanthone from Artocarpus kemando (Moraceae).

Aster ageratoides

1 reference

Two New Tetracyclic Triterpenoids and Other Constituents fromAster Ageratoides var. Oophyllus

Astragalus schahrudensis

1 reference

Triterpene glycosides of astragalus and their genins. XXVI. Cycloartanes and sterols of Astragalus schachirudensis

Axinella cannabina

1 reference

Minor and trace sterols in marine invertebrates. Part 35. Isolation and structure elucidation of seventy-four sterols from the sponge Axinella cannabina

Caulerpa prolifera

1 reference

Three squalene derivatives from Caulerpa prolifera

Cissus quadrangularis

1 reference

Two unsymmetric tetracyclic triterpenoids from cissus quadrangularis

Clerodendrum infortunatum

1 reference

The 24α- and 24β-epimers of 24-ethylcholesta-5,22-dien-3β-ol in two Clerodendrum species

Cliona celata

2 references

Sterols from the sponges Cliona celata grant and Hymeniacidon perleve montagu

CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. VIII. THE STEROL OF SPONGES: CLIONASTEROL AND PORIFERASTEROL

Coriaria intermedia

1 reference

20-Epibryonolic acid, phytosterols and ellagic acid from Coriaria intermedia

Coriaria japonica

1 reference

20-Epibryonolic acid, phytosterols and ellagic acid from Coriaria intermedia

Croton costatus

1 reference

Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae).

Croton skutchii

1 reference

Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae).

Dalbergia monetaria

1 reference

Inhaltsstoffe der Rinde vonDalbergia monetaria L. Drei neue Isoflavon-C-glucoside

Daucus carota

1 reference

Coumarins ofDaucus carota

Dumortiera hirsuta

1 reference

Sesquiterpene and other constituents of the liverwort Dumortiera hirsuta

Euphorbia nivulia

1 reference

Cycloart-25-en-2β-ol from Euphorbia nivulia

Eutreptia viridis

1 reference

Sterols of the cultured euglenid Eutreptia viridis: a novel delta 23-unsaturated sterol

Diplopterygium glaucum

1 reference

Triterpene Alcohols and Sterols from the Fern Gleichenia japonica SPR.

Gleichenia japonica

1 reference

Triterpene Alcohols and Sterols from the Fern Gleichenia japonica SPR.

Haplophyllum obtusifolium

1 reference

Obtusinin ? A new coumarin fromHaplophyllum obtusifolium

Humboldtia laurifolia

1 reference

3,5,7,3′,5′-Pentahydroxyflavan and 3α-methoxyfriedelan from Humboldtia laurifolia

Water net

1 reference

24-Methylene-25-methylcholesterol and both C-24 epimers of 24-ethyl-22-dehydrocholesterol in a freshwater green algaHydrodictyon reticulatum

Juniperus formosana

1 reference

Dehydroabietane diterpenes from Juniperus formosana hay. var. concolor hay

Kalanchoe marmorata

1 reference

Co-occurrence of C-24 epimeric 24-ethylsterols possessing and lacking a Δ25-bond inKalanchoe petitiana

Kalanchoe petitiana

1 reference

Co-occurrence of C-24 epimeric 24-ethylsterols possessing and lacking a Δ25-bond inKalanchoe petitiana

Khaya senegalensis

1 reference

Rearranged limonoids from Khaya senegalensis

Lamium amplexicaule

1 reference

Components and antimicrobial activity of Lamium amplexicaule from Algeria

Ligularia veitchiana

1 reference

Eremophilanolides from the roots of Ligularia veitchiana

common periwinkle

1 reference

Sterols of marine mollusks; the sterols of the periwinkle, Littorina littorea

Melilotus messanensis

1 reference

Bioactive Steroids and Triterpenes from Melilotus messanensis and Their Allelopathic Potential

Melilotus siculus

1 reference

Bioactive Steroids and Triterpenes from Melilotus messanensis and Their Allelopathic Potential

Neofibularia nolitangere

1 reference

Sterols from the Caribbean sponge Neofibularia nolitangere. Isolation of two novel polyhydroxysteroids

Alitta succinea

1 reference

Sex pheromones in marine polychaetes: steroids from ripe Nereis succinea

Neanthes succinea

1 reference

Sex pheromones in marine polychaetes: steroids from ripe Nereis succinea

Oxalis pes-caprae

1 reference

Cinnamic Ester Derivatives fromOxalis pes-caprae(Bermuda Buttercup)#

Paeonia × suffruticosa

1 reference

Two novel compounds from Paeonia suffructicosa

Axinella aruensis

1 reference

Minor and trace sterols in marine invertebrates. 61. Isolation and structure elucidation of new A-nor sterols from the marine sponge Phakellia aruensis

Phlomoides ostrowskiana

1 reference

Components ofPhlomis ostrowskiana

Phytolacca acinosa

1 reference

Phytolaccanol and epiacetylaleuritolic acid, two triterpenoids from Phytolacca acinosa

Piper umbellatum

1 reference

Bioactive aristolactams from Piper umbellatum

Millettia pinnata

2 references

Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra

Chemical Examination of Flowers ofPongamia glabra

Pongamia pinnata

2 references

Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra

Chemical Examination of Flowers ofPongamia glabra

Catunaregam spinosa

1 reference

Triterpenoids from Randia dumetorum

Saussurea medusa

1 reference

Bioactive constituents from Chinese natural medicines. XV. Inhibitory effect on aldose reductase and structures of Saussureosides A and B from Saussurea medusa

Calyptocarpus vialis

1 reference

Sesquiterpene lactones and other constituents of Stevia maimarensis and Synedrellopsis grisebachii

Synedrellopsis grisebachii

1 reference

Sesquiterpene lactones and other constituents of Stevia maimarensis and Synedrellopsis grisebachii

Tanacetum argenteum

1 reference

A guaianolide from Tanacetum argenteum subsp. flabellifolium

Tephrosia purpurea

1 reference

A coumestone from the roots of Tephrosia hamiltonii

Virola guggenheimii

1 reference

Eusiderins and 1,3-diarylpropanes from Virola species

Dalbergia ovalis

1 reference

Inhaltsstoffe der Rinde vonDalbergia monetaria L. Drei neue Isoflavon-C-glucoside

Scandosorbus intermedia

1 reference

20-Epibryonolic acid, phytosterols and ellagic acid from Coriaria intermedia

Monteverdia guyanensis

1 reference

A sesquiterpene evoninoate alkaloid from Maytenus guianensis

Vachellia nilotica

1 reference

γ-Sitosterol from Acacia nilotica L. induces G2/M cell cycle arrest and apoptosis through c-Myc suppression in MCF-7 and A549 cells.

Cynomorium songaricum

1 reference

GC-MS analysis of liposoluble constituents from the stems of Cynomorium songaricum

Flabellia petiolata

1 reference

Udoteal B, A New Linear Diterpenoid from the Green AlgaUdotea petiolata

Ulva popenguinensis

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Enteromorpha linza

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Azolla nilotica

1 reference

Chemical constituents of aquatic fern Azolla nilotica

Salvia palaestina

1 reference

Modified abietane diterpenoids and a methoxylupane derivative from Salvia palaestina

Salvia triloba

1 reference

Constituents from Salvia triloba

Salvia jaminiana

1 reference

Components and antibacterial activity of the roots of Salvia jaminiana

Teucrium leucocladum

1 reference

Chemical analysis and biological activities of the essential oil of Teucrium leucocladum Boiss. (Lamiaceae)

1 reference

1 reference

Clionosterol and ethyl cholestan-22-enol isolated from the rhizome of Polygala tenuifolia inhibit phosphatidylinositol 3-kinase/Akt pathway

Elaeis guineensis

1 reference

Involvement of metabolites in early defense mechanism of oil palm (Elaeis guineensis Jacq.) against Ganoderma disease

Ulva linza

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Hydropuntia edulis

2 references

Dihydroxysterols from the marine red alga, Gracilaria edulis

Minor C29-steroids from the marine red alga, Gracilaria edulis

Salvia fruticosa

1 reference

Constituents from Salvia triloba

Kalanchoe pinnata

1 reference

Sterols ofKalanchoe pinnata: First report of the isolation of both C-24 epimers of 24-alkyl-Δ25-sterols from a higher plant

Achillea tenuifolia

1 reference

Further constituents of Achillea ageratum

Achillea cretica

1 reference

Further constituents of Achillea ageratum

subject has role

hypolipidemic

1 reference

Medical Subject Headings

MeSH descriptor ID

C025473

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1

15 March 2018

Identifiers

InChI

1 reference

Clionasterol (English)

14 October 2016

2 references

Clionasterol (English)

14 October 2016

ChEBI release 2020-09-01

CAS Registry Number

83-47-6

2 references

Global Substance Registration System

γ-sitosterol (English)

14 October 2016

https://commonchemistry.cas.org/detail?cas_rn=83-47-6

10 April 2021

1 reference

clionasterol (English)

14 October 2016

2 references

Clionasterol (English)

14 October 2016

ChEBI ID

132823

mapping relation type

exact match

2 references

ChEBI release 2019-10-02

International Chemical Identifier

InChI

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1

SureChEMBL ID

SCHEMBL219424

2 references

1 reference

1 reference

EC number

201-481-1

1 reference

Global Substance Registration System

γ-sitosterol (English)

ECHA Substance Infocard ID

14 October 2016

100.001.347

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.001.347

27 December 2018

(3β,24S)-stigmast-5-en-3-ol (English)

quotation

CAS no.: 83-47-6 (English)

MeSH descriptor ID

C025473

1 reference

Medical Subject Headings

MeSH descriptor ID

C025473

Human Metabolome Database ID

14 March 2018

HMDB0000649

2 references

2 references

Global Substance Registration System

γ-sitosterol (English)

14 October 2016

http://www.lipidmaps.org/rest/compound/lm_id/LM/all/download

1 reference