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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:41 UTC
NP-MRD IDNP0001031
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-Sitosterol
DescriptionBeta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID: 13129445 , 11432711 ). Beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID: 10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID: 14652381 ). Beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID: 12579296 ).
Structure
Thumb
Synonyms
ValueSource
(-)-beta-SitosterolChEBI
(24R)-Ethylcholest-5-en-3beta-olChEBI
(24R)-Stigmast-5-en-3beta-olChEBI
(3beta)-Stigmast-5-en-3-olChEBI
22,23-DihydrostigmasterolChEBI
24alpha-EthylcholesterolChEBI
alpha-DihydrofucosterolChEBI
AzuprostatChEBI
beta-SitosterinChEBI
CupreolChEBI
NimbosterolChEBI
TriastonalChEBI
HarzolKegg
SitosterolKegg
(-)-b-SitosterolGenerator
(-)-Β-sitosterolGenerator
(24R)-Ethylcholest-5-en-3b-olGenerator
(24R)-Ethylcholest-5-en-3β-olGenerator
(24R)-Stigmast-5-en-3b-olGenerator
(24R)-Stigmast-5-en-3β-olGenerator
(3b)-Stigmast-5-en-3-olGenerator
(3Β)-stigmast-5-en-3-olGenerator
24a-EthylcholesterolGenerator
24Α-ethylcholesterolGenerator
a-DihydrofucosterolGenerator
Α-dihydrofucosterolGenerator
b-SitosterinGenerator
Β-sitosterinGenerator
b-SitosterolGenerator
Β-sitosterolGenerator
22,23-Dihydro-stigmasterolHMDB
a-PhytosterolHMDB
alpha-PhytosterolHMDB
AngelicinHMDB
beta-PhytosterolHMDB
CincholHMDB
D5-Stigmasten-3b-olHMDB
Delta5-Stigmasten-3b-olHMDB
PhytosterolHMDB
ProstasalHMDB
QuebracholHMDB
RhamnolHMDB
Sito-landeHMDB
SobatumHMDB
Stigmast-5-en-3-olHMDB
Stigmast-5-en-3b-olHMDB
3beta-SitosterolHMDB
24-Ethylcholest-5-en-3 beta-olHMDB
24-EthylcholesterolHMDB
ClionasterolHMDB
3beta-Stigmast-5-en-3-olHMDB
Sitosterol, (3beta)-isomerHMDB
Stigmast-5-en-3beta-olHMDB
Stigmast-5-en-3β-olHMDB
delta5-Stigmasten-3beta-olHMDB
Δ5-stigmasten-3β-olHMDB
Α-phytosterolHMDB
RhammolHMDB
Δ5-stigmasten-3beta-olHMDB
beta-SitosterolChEBI
Chemical FormulaC29H50O
Average Mass414.7180 Da
Monoisotopic Mass414.38617 Da
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number83-46-5
SMILES
[H][C@@](CC)(CC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)C
InChI Identifier
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
InChI KeyKZJWDPNRJALLNS-VJSFXXLFSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Achillea alexandri-regis Bornm.& RudskiKNApSAcK Database
Achyrocline tomentosaKNApSAcK Database
Adansonia digitataKNApSAcK Database
Adenosma caeruleumKNApSAcK Database
Adiantum caudatumKNApSAcK Database
Aesculus punduanaKNApSAcK Database
Agave mellifluaKNApSAcK Database
Agave palmarisKNApSAcK Database
Aglaia rubiginosaKNApSAcK Database
Ailanthus altissimaKNApSAcK Database
Ajania fruticulosaKNApSAcK Database
Ajuga taiwanensisKNApSAcK Database
Alchornea cordifoliaKNApSAcK Database
Aleurites fordii Hemsl.KNApSAcK Database
Alpinia pinnanensisKNApSAcK Database
Amentotaxus yunnanensisKNApSAcK Database
Amsonia angustifoliaKNApSAcK Database
Andrographis paniculataKNApSAcK Database
Angelica furcijuga KITAGAWAKNApSAcK Database
Anisomeles indicaKNApSAcK Database
Annona purpureaKNApSAcK Database
Annona reticulataKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Aristolochia elegansKNApSAcK Database
Aristolochia heterophylla HemslKNApSAcK Database
Aristolochia kaempferiKNApSAcK Database
Aristolochia manshuriensisKNApSAcK Database
Aristolochia pubescensKNApSAcK Database
Artabotrys uncinatusKNApSAcK Database
Artemisia annua L.KNApSAcK Database
Artemisia minorKNApSAcK Database
Artemisia sieversianaKNApSAcK Database
Artemisia vulgarisKNApSAcK Database
Asparagus racemosusKNApSAcK Database
Asparagus tenuifoliumKNApSAcK Database
Asphodeline globiferaKNApSAcK Database
Asplenium laciniatumKNApSAcK Database
Astragalus glycyphyllosKNApSAcK Database
Atta sexdens rubropilosaKNApSAcK Database
Averrhoa carambolaKNApSAcK Database
Azadirachta indicaKNApSAcK Database
Ballota limbataKNApSAcK Database
Bauhinia candicansKNApSAcK Database
Bauhinia vahlii L.KNApSAcK Database
Begonia nantoensisKNApSAcK Database
Beilschmiedia anacardiolidesKNApSAcK Database
Beilschmiedia zenkeriKNApSAcK Database
Berberis pseudanubalataKNApSAcK Database
Bergenia ligulataKNApSAcK Database
Bituminaria bituminosaKNApSAcK Database
Blepharis sindicaKNApSAcK Database
Blutaparon portulacoidesKNApSAcK Database
Boehmeria holosericeaKNApSAcK Database
Boehmeria tricuspisKNApSAcK Database
Borassus flabelliferKNApSAcK Database
Boswellia papyriferaKNApSAcK Database
Brosimum acutifoliumKNApSAcK Database
Buddleja madagascariensisKNApSAcK Database
Caesalpinia pulcherrimaKNApSAcK Database
Callicarpa arboreaKNApSAcK Database
Callicarpa integerrimaKNApSAcK Database
Callicarpa macrophyllaKNApSAcK Database
Callicarpa pilosissimaKNApSAcK Database
Calophyllum bracteatumKNApSAcK Database
Calophyllum trapezifoliumKNApSAcK Database
Cannabis inflorescencesKNApSAcK Database
Capparis aegyptiaKNApSAcK Database
Capparis desertiKNApSAcK Database
Capparis leucophyllaKNApSAcK Database
Caragana microphyllaKNApSAcK Database
Casearia ilicifoliaKNApSAcK Database
Cassia dentataKNApSAcK Database
Cassia javanicaKNApSAcK Database
Cassia macranthaKNApSAcK Database
Cassia multijugaKNApSAcK Database
Cassia siameaKNApSAcK Database
Cassia speciosaKNApSAcK Database
Casuarina equisetifolia L.KNApSAcK Database
Casuarina junghanianaKNApSAcK Database
Casuarina rigidaKNApSAcK Database
Ceiba pentandraKNApSAcK Database
Celtis laevigataKNApSAcK Database
Centaurea cineraria L.KNApSAcK Database
Centrosema pubescensKNApSAcK Database
Chaenomeles sinensis KOEHNEKNApSAcK Database
Chamaecyparis formosensisKNApSAcK Database
Chione venosa (sw.) Urban var.venosaKNApSAcK Database
Cichorium intybusKNApSAcK Database
Cinnamomum subaveniumKNApSAcK Database
Cinnamomum tenuifoliumKNApSAcK Database
Cinnamosma madagascariensisKNApSAcK Database
Cipadessa boivininaKNApSAcK Database
Cipadessa cinerascensKNApSAcK Database
Clarisia racemosa R.et P.KNApSAcK Database
Clausena pentaphylla (Roxb.)DC.KNApSAcK Database
Cleidion spiciflorum (Burm. f.) Merr.KNApSAcK Database
Cleistocalyx operculatusKNApSAcK Database
Clerodendron neutensKNApSAcK Database
Coccoloba excoriataKNApSAcK Database
Coffea canephoraKNApSAcK Database
Coffea charrierianaKNApSAcK Database
Coffea congensisKNApSAcK Database
Coffea eugenioidesKNApSAcK Database
Coffea hetero calyxKNApSAcK Database
Coffea humblotianaKNApSAcK Database
Coffea humilisKNApSAcK Database
Coffea kapakataKNApSAcK Database
Coffea liberica var.dewevreiKNApSAcK Database
Coffea liberica var.libericaKNApSAcK Database
Coffea pseudozanguebariaeKNApSAcK Database
Coffea racemosaKNApSAcK Database
Coffea salvatrixKNApSAcK Database
Coffea sessilifloraKNApSAcK Database
Coffea stenophyllaKNApSAcK Database
Combretum quadrangulareKNApSAcK Database
Commiphora confusaKNApSAcK Database
Cornus kousaKNApSAcK Database
Corylus avellanaKNApSAcK Database
Corylus maximaKNApSAcK Database
Costus speciosusKNApSAcK Database
Couepia polyandraKNApSAcK Database
Coussarea brevicaulisKNApSAcK Database
Cremanthodium ellisiiKNApSAcK Database
Crotalaria assamicaKNApSAcK Database
Crotalaria pallidaKNApSAcK Database
Crotalaria walkeriKNApSAcK Database
Croton arboreousKNApSAcK Database
Croton lechleri Mull.Arg.KNApSAcK Database
Croton urucuranaKNApSAcK Database
Croton urucurana Baill.KNApSAcK Database
Croton zambesicusKNApSAcK Database
Cryptocarya idenburgensisKNApSAcK Database
Cymbopogon flexuosusKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cynanchum taiwanianumKNApSAcK Database
Dalbergia odoriferaKNApSAcK Database
Dalbergia volubilisKNApSAcK Database
Dalea tuberculataKNApSAcK Database
Daphne odoraKNApSAcK Database
Dendrobium nobile Lindl.KNApSAcK Database
Derris obtusaKNApSAcK Database
Dichrostachys cinerea Maab.KNApSAcK Database
Dicliptera ripariaKNApSAcK Database
Dictamnus angustifoliusKNApSAcK Database
Dictamnus hispanicusKNApSAcK Database
Dictyoloma vandellianumKNApSAcK Database
Dioscorea colletiiKNApSAcK Database
Dioscorea cyphocarpaKNApSAcK Database
Dioscorea oppositaKNApSAcK Database
Diospyros acutaKNApSAcK Database
Diospyros buxifoliaKNApSAcK Database
Diospyros chaetocarpaKNApSAcK Database
Diospyros chloroxylonKNApSAcK Database
Diospyros cordifoliaKNApSAcK Database
Diospyros discolorKNApSAcK Database
Diospyros ebenasterKNApSAcK Database
Diospyros ebenumKNApSAcK Database
Diospyros erianthaKNApSAcK Database
Diospyros ferreaKNApSAcK Database
Diospyros hirsutaKNApSAcK Database
Diospyros indicaKNApSAcK Database
Diospyros kakiKNApSAcK Database
Diospyros kirkiiKNApSAcK Database
Diospyros lotusKNApSAcK Database
Diospyros malanonilauKNApSAcK Database
Diospyros melanoxylonKNApSAcK Database
Diospyros montanaKNApSAcK Database
Diospyros mooniiKNApSAcK Database
Diospyros morrisianaKNApSAcK Database
Diospyros oblongifoliaKNApSAcK Database
Diospyros oppositifoliaKNApSAcK Database
Diospyros peregrinaKNApSAcK Database
Diospyros quaesitaKNApSAcK Database
Diospyros rheophyticaKNApSAcK Database
Diospyros rhodocalyxKNApSAcK Database
Diospyros spinescensKNApSAcK Database
Diospyros texanaKNApSAcK Database
Diospyros thwaitesiiKNApSAcK Database
Diospyros tomentosaKNApSAcK Database
Diospyros walkeriKNApSAcK Database
Disporopsis asperaKNApSAcK Database
Dorstenia angusticornisKNApSAcK Database
Dorstenia barteri var. subtriangularisKNApSAcK Database
Dorstenia zenkeriKNApSAcK Database
Dracaena dracoKNApSAcK Database
Dryopteris crassirhizomaKNApSAcK Database
Drypetes inaequalisKNApSAcK Database
Drypetes tessmannianaKNApSAcK Database
Duranta plumieriKNApSAcK Database
Dysoxylum macranthumKNApSAcK Database
Eleutherococcus senticosus Rupr.and Maxim.KNApSAcK Database
Embelia ribes Burm.KNApSAcK Database
Enhalus acoroidesKNApSAcK Database
Enkianthus cernuusKNApSAcK Database
Entada scandensKNApSAcK Database
Ephedra campylopodaKNApSAcK Database
Ephedra sinicaKNApSAcK Database
Epigaea asiaticaKNApSAcK Database
Eriolaena hookerianaKNApSAcK Database
Erycibe expansaKNApSAcK Database
Erysimum carniolicumKNApSAcK Database
Erythrina arborescens Roxb.KNApSAcK Database
Eucalyptus camaldulensis var.obtusaKNApSAcK Database
Eucalyptus citriodoraKNApSAcK Database
Eucalyptus cladocalyxKNApSAcK Database
Euonymus alatusKNApSAcK Database
Eupatorium macrocephalum Lee.KNApSAcK Database
Euphorbia guyonianaKNApSAcK Database
Euphorbia indicaKNApSAcK Database
Euphorbia lathyrisKNApSAcK Database
Euphorbia micractinaKNApSAcK Database
Euphorbia paraliasKNApSAcK Database
Euphorbia pulcherrimaKNApSAcK Database
Euphorbia segetalisKNApSAcK Database
Euphorbia sessiliflora Roxb.KNApSAcK Database
Euphorbia tanquahueteKNApSAcK Database
Euphorbia tirucalliKNApSAcK Database
Eysenhardtia platycarpaKNApSAcK Database
Fagara heitziiKNApSAcK Database
Fagara tessmannii Engl.KNApSAcK Database
Falcatifolium taxoidesKNApSAcK Database
Ferula assa-foetidaKNApSAcK Database
Ferula diversivittataKNApSAcK Database
Ferula szowitsianaKNApSAcK Database
Ficus bengalensisKNApSAcK Database
Ficus caricaKNApSAcK Database
Ficus eriobotryoidesKNApSAcK Database
Ficus palmataKNApSAcK Database
Ficus septicaKNApSAcK Database
Flindersia laevicarpa C.T.White et Francis.KNApSAcK Database
Frullania brasiliensisKNApSAcK Database
Frullania monoceraKNApSAcK Database
Garcinia afzelii ENGL.KNApSAcK Database
Garcinia echinocarpaKNApSAcK Database
Garcinia mangostana L.KNApSAcK Database
Garcinia multifloraKNApSAcK Database
Garcinia polyanthaKNApSAcK Database
Garcinia terpnophyllaKNApSAcK Database
Gentiana lutea L.KNApSAcK Database
Geranium macrorrhizum L.KNApSAcK Database
Ginkgo biloba L.KNApSAcK Database
Gleditsia sinensis LAM.KNApSAcK Database
Glochidion puberumKNApSAcK Database
Glycine maxKNApSAcK Database
Gnaphalium pellitumKNApSAcK Database
Gomphrena celosioidesKNApSAcK Database
Guarea macrophyllaKNApSAcK Database
Guazuma tomentosaKNApSAcK Database
Halodule uninervisKNApSAcK Database
Halophila ovalisKNApSAcK Database
Halophila ovataKNApSAcK Database
Halophila spinulosaKNApSAcK Database
Haplophyllum acutifoliumKNApSAcK Database
Hedysarum multijugumKNApSAcK Database
Helicteres angustifoliaKNApSAcK Database
Heliotropium indicumKNApSAcK Database
Henriettella fascicularisKNApSAcK Database
Heracleum granatenseKNApSAcK Database
Heterothalamus spartioidesKNApSAcK Database
Hippophae rhamnoides L.KNApSAcK Database
Hordeum vulgare L.cv MammutKNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Hydrangea heteromallaKNApSAcK Database
Hypericum carinatumKNApSAcK Database
Hypericum japonicumKNApSAcK Database
Indigofera tetranthaKNApSAcK Database
Inula cappaKNApSAcK Database
Inula racemosaKNApSAcK Database
Inula viscosaKNApSAcK Database
Iris germanica L.KNApSAcK Database
Iris tenuifoliaKNApSAcK Database
Isatis indigoticaKNApSAcK Database
Isodon japonicaKNApSAcK Database
Jatropha weddellianaKNApSAcK Database
Juglans mandshuricaKNApSAcK Database
Juglans regiaKNApSAcK Database
Junellia tridensKNApSAcK Database
Juniperus brevifoliaKNApSAcK Database
Justicia heterocarpa T.ANDERSKNApSAcK Database
Kadsura heteroclitaKNApSAcK Database
Kalmia latifolia L.KNApSAcK Database
Khaya ivorensisKNApSAcK Database
Khaya senegalensis L.KNApSAcK Database
Laennecia sophiifolia (Kunth) G.L.NesomKNApSAcK Database
Larix kaempferi (Lamb.) CarrKNApSAcK Database
Lasianthus gardneriKNApSAcK Database
Launaea nudicaulisKNApSAcK Database
Leonurus persicusKNApSAcK Database
Lespedeza bicolorKNApSAcK Database
Leucothoe grayana Max.KNApSAcK Database
Ligularia odontomanesKNApSAcK Database
Litsea japonicaKNApSAcK Database
Lonicera quinquelocularisKNApSAcK Database
Loranthus falcatusKNApSAcK Database
Machilus zuihoensisKNApSAcK Database
Magnolia obovataKNApSAcK Database
Markhamia stipulataKNApSAcK Database
Maytenus guianensisKNApSAcK Database
Maytenus loevisKNApSAcK Database
Medicago sativaKNApSAcK Database
Melastoma intermediumKNApSAcK Database
Melianthus majorKNApSAcK Database
Melicope octandraKNApSAcK Database
Melicope semecarpifoliaKNApSAcK Database
Mentha longifoliaKNApSAcK Database
Microtropis fokienensisKNApSAcK Database
Microtropis japonicaKNApSAcK Database
Millettia brandisianaKNApSAcK Database
Millettia conrauiKNApSAcK Database
Mimosa rubicaulisKNApSAcK Database
Mirabilis jalpaKNApSAcK Database
Momordica charantiaKNApSAcK Database
Morinda citrifolia LKNApSAcK Database
Morus insignisKNApSAcK Database
Mussaenda macrophyllaKNApSAcK Database
Myrianthus arboreusKNApSAcK Database
Nauclea orientalisKNApSAcK Database
Neoboutonia glabrescens PrainKNApSAcK Database
Neoboutonia melleriKNApSAcK Database
Neochamaelea pulverulentaKNApSAcK Database
Neolitsea aciculataKNApSAcK Database
Neolitsea acuminatissimaKNApSAcK Database
Neolitsea konishiiKNApSAcK Database
Neolitsea parvigemmaKNApSAcK Database
Neolitsea sericeaKNApSAcK Database
Newbouldia laevisKNApSAcK Database
Nicotiana benthamianaKNApSAcK Database
Nothofagus pumilioKNApSAcK Database
Nymphaea caeruleaKNApSAcK Database
Ocimum spicatumKNApSAcK Database
Ophiorrhiza liukiuensisKNApSAcK Database
Oriciopsis glaberrima ENGL.KNApSAcK Database
Orthosiphon stamineusKNApSAcK Database
Paederia foetidaKNApSAcK Database
Parasitaxus ustaKNApSAcK Database
Pedilanthus tithymaloidesKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Pelargonium sidoidesKNApSAcK Database
Pellia epiphyllaKNApSAcK Database
Periploca aphyllaKNApSAcK Database
Pharbitis nilKNApSAcK Database
Phellodendron amurense var.wilsoniiKNApSAcK Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phyllanthus niruriKNApSAcK Database
Phyllanthus oligospermusKNApSAcK Database
Phyllanthus reticulatusKNApSAcK Database
Phyllostachys edulisKNApSAcK Database
Picramnia antidesmaKNApSAcK Database
Picramnia latifoliaKNApSAcK Database
Pieris japonica D.Don.KNApSAcK Database
Pileostegia viburnoides var. glabrescensKNApSAcK Database
Pimpinella thellungianaKNApSAcK Database
Pinellia pedatisectaKNApSAcK Database
Pinus koraiensisKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Pinus taedaKNApSAcK Database
Piper acutisleginumKNApSAcK Database
Piper aduncumKNApSAcK Database
Piper attenuatumKNApSAcK Database
Piper betleKNApSAcK Database
Piper brachystachyumKNApSAcK Database
Piper khasianaKNApSAcK Database
Piper nigrum L.KNApSAcK Database
Piper pedicellosumKNApSAcK Database
Piper peepuloidesKNApSAcK Database
Piper philippinumKNApSAcK Database
Piper retrofractum Vahl.KNApSAcK Database
Piper solmsianumKNApSAcK Database
Piper thomsoniKNApSAcK Database
Piper umbellatumKNApSAcK Database
Piptadenia macrocarpaKNApSAcK Database
Plectranthus rugosusKNApSAcK Database
Pleodendron costaricenseKNApSAcK Database
Pluchea sericeaKNApSAcK Database
Plumbago zeylanicaKNApSAcK Database
Poinsettia pulcherrimaKNApSAcK Database
Polyalthia longifolia var.pendulaKNApSAcK Database
Polygonum bistortaKNApSAcK Database
Polytrichum communeKNApSAcK Database
Poncirus trifoliataKNApSAcK Database
Populus pseudosimoniiKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Prosopis glandulosaKNApSAcK Database
Prosopis spicigeraKNApSAcK Database
Prumnopitys ferruginoidesKNApSAcK Database
Pseudotsuga wilsonianaKNApSAcK Database
Psychotria adenophyllaKNApSAcK Database
Pteridium aquilinumKNApSAcK Database
Pteris wallichianaKNApSAcK Database
Pterocarpus santalinusKNApSAcK Database
Pterodon apraricioiKNApSAcK Database
Punica granatumKNApSAcK Database
Quercus glauca Thunb.KNApSAcK Database
Quercus myrsenaefoliaKNApSAcK Database
Quercus stenophylla Makino.KNApSAcK Database
Raphanus sativusKNApSAcK Database
Rhus wallichiKNApSAcK Database
Robinsonecio gerberifoliusKNApSAcK Database
Rosa mutifloraKNApSAcK Database
Rourea santaloidesKNApSAcK Database
Rubia cordifolia L.KNApSAcK Database
Rubia wallichiana DECNEKNApSAcK Database
Rubia yunnanensisKNApSAcK Database
Rubus ellipticusKNApSAcK Database
Ruellia tuberosaKNApSAcK Database
Ruppia maritimaKNApSAcK Database
Sabal causiarumKNApSAcK Database
Salvia aegyptiacaKNApSAcK Database
Salvia aethiopisKNApSAcK Database
Salvia amplexicaulis Lam.KNApSAcK Database
Salvia canariensis L.KNApSAcK Database
Salvia kronenburgiiKNApSAcK Database
Salvia multicaulisKNApSAcK Database
Salvia nicolsonianaKNApSAcK Database
Salvia officinalisKNApSAcK Database
Salvia syriaca L.KNApSAcK Database
Sambucus canadensisKNApSAcK Database
Sambucus nigra.KNApSAcK Database
Sapium sebiferumKNApSAcK Database
Sargentodoxa cuneataKNApSAcK Database
Saussurea lanicepsKNApSAcK Database
Saussurea muliensisKNApSAcK Database
Scabiosa soongoricaKNApSAcK Database
Schleichera oleosaKNApSAcK Database
Schleichera trijugaKNApSAcK Database
Schnabelia tetradontaKNApSAcK Database
Scleropyrum wallichianumKNApSAcK Database
Scrophularia ningpoensisKNApSAcK Database
Senecio chionophilusKNApSAcK Database
Senecio viraviraKNApSAcK Database
Seseli tortuosum LBS.Eur.KNApSAcK Database
Severinia buxifoliaKNApSAcK Database
Sideritis argosphacelus var. spicataKNApSAcK Database
Sideritis candicans var.eriocephalaKNApSAcK Database
Sideritis discolorKNApSAcK Database
Sideritis kueglerianaKNApSAcK Database
Sideritis lotsyiKNApSAcK Database
Sideritis lotsyi var. mascaensisKNApSAcK Database
Sideritis solutaKNApSAcK Database
Sideritis tenoiKNApSAcK Database
Skimmia wallachiiKNApSAcK Database
Smilax chinaKNApSAcK Database
Solanum chacoense Bitt.KNApSAcK Database
Solanum tuberosum L.KNApSAcK Database
Sophora japonica L.KNApSAcK Database
Spiraea formosanaKNApSAcK Database
Stemodia foliosaKNApSAcK Database
Strychnos dolychothyrsaKNApSAcK Database
Strychnos potatorumKNApSAcK Database
Symphytum tuberosumKNApSAcK Database
Symplocos racemosaKNApSAcK Database
Tamus communis L.KNApSAcK Database
Tanacetum longifoliumKNApSAcK Database
Taraxacum formosanumKNApSAcK Database
Taxodium lanceolataKNApSAcK Database
Taxus baccataKNApSAcK Database
Taxus brevifoliaKNApSAcK Database
Taxus canadensisKNApSAcK Database
Taxus cuspidataKNApSAcK Database
Taxus floridanaKNApSAcK Database
Taxus maireiKNApSAcK Database
Taxus wallichianaKNApSAcK Database
Tephrosia purpureaKNApSAcK Database
Terminalia superbaKNApSAcK Database
Ternstroemia gymnantheraKNApSAcK Database
Tetracentron sinenseKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thevetia peruvianaKNApSAcK Database
Toona ciliataKNApSAcK Database
Toona sinensisKNApSAcK Database
Tovomita brasiliensisKNApSAcK Database
Tribulus terrestrisKNApSAcK Database
Trichilia estipulataKNApSAcK Database
Trichosanthes kirilowiiKNApSAcK Database
Trigonella foenum-graceumKNApSAcK Database
Tripterygium hypoglaucumKNApSAcK Database
Triticum aestivumKNApSAcK Database
Triticum spp.KNApSAcK Database
Tupistra chinensisKNApSAcK Database
Veratrum albumKNApSAcK Database
Verbena brasiliensis VELLKNApSAcK Database
Virola surinamensisKNApSAcK Database
Viscum coloratumKNApSAcK Database
Vitex trifoliaKNApSAcK Database
Withania somniferaKNApSAcK Database
Xanthium strumariumKNApSAcK Database
Xylopia aromaticaKNApSAcK Database
Xylopia brasiliensisKNApSAcK Database
Xylopia emarginataKNApSAcK Database
Zanthoxylum culantrilloKNApSAcK Database
Zanthoxylum integrifoliolumKNApSAcK Database
Zanthoxylum myriacanthumKNApSAcK Database
Zanthoxylum podocarpum Hemsl.KNApSAcK Database
Zanthoxylum simulansKNApSAcK Database
Zanthoxylum wutaienseKNApSAcK Database
Zea maysKNApSAcK Database
Zingiber aromaticumKNApSAcK Database
Zingiber officinaleKNApSAcK Database
Species Where Detected
Species NameSourceReference
Allomyces macrogynusKNApSAcK Database
Aspergillus oryzaeKNApSAcK Database
Aureoumbra lagunensisKNApSAcK Database
Candida sp.KNApSAcK Database
Candida utilisKNApSAcK Database
Coriolus versicolorKNApSAcK Database
Fusarium sporotrichioidesKNApSAcK Database
Glomus mosseaeKNApSAcK Database
Monascus pilosus BCRC38072KNApSAcK Database
Physarum polycephalumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling Point498.00 to 501.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10 mg/mLNot Available
LogP10.482 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
External Links
HMDB IDHMDB0000852
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012362
KNApSAcK IDC00023770
Chemspider ID192962
KEGG Compound IDC01753
BioCyc IDCPD-4143
BiGG IDNot Available
Wikipedia LinkBeta-Sitosterol
METLIN ID169
PubChem Compound222284
PDB IDNot Available
ChEBI ID27693
Good Scents IDrw1223271
References
General References
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  2. Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13. [PubMed:8253356 ]
  3. Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9. [PubMed:8028508 ]
  4. Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. Epub 2005 Apr 12. [PubMed:15824923 ]
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  6. Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63. [PubMed:15989725 ]
  7. Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. [PubMed:7596226 ]
  8. Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6. [PubMed:11240845 ]
  9. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. [PubMed:16477216 ]
  10. Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [PubMed:1499139 ]
  11. Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. [PubMed:15893885 ]
  12. Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9. [PubMed:8429265 ]
  13. Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8. [PubMed:15816807 ]
  14. Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20. [PubMed:15726313 ]
  15. Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9. [PubMed:10695663 ]
  16. Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. [PubMed:573140 ]
  17. Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4. [PubMed:10810360 ]
  18. Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801. [PubMed:15936608 ]
  19. Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73. [PubMed:14615068 ]
  20. Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. Epub 2005 Feb 12. [PubMed:15939057 ]
  21. Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. [PubMed:14652381 ]
  22. Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. [PubMed:11432711 ]
  23. Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. [PubMed:13129445 ]
  24. Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. [PubMed:10368239 ]
  25. Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. [PubMed:12579296 ]