CHEBI:27693 - sitosterol

Main ChEBI Ontology Automatic Xrefs
ChEBI Name sitosterol
ChEBI ID CHEBI:27693
Definition A phytosterols that is stigmast-5-ene substituted by a β-hydroxy group at position 3.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:26692, CHEBI:9170
Supplier Information
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Formula C29H50O
Net Charge 0
Average Mass 414.70670
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
InChIKey KZJWDPNRJALLNS-VJSFXXLFSA-N
SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C
Metabolite of Species Details
Garcia parviflora (IPNI:107401-2) Found in leaf (BTO:0000713). n-hexane extract of air-dried, powdered branch and leaves See: PubMed
Garcia parviflora (IPNI:107401-2) Found in branch (BTO:0000148). n-hexane extract of air-dried, powdered branch and leaves See: PubMed
Beilschmiedia tsangii (IPNI:462970-1) Found in root (BTO:0001188). Cold MeOH extract of dry roots See: PubMed
Neolitsea daibuensis (IPNI:466954-1) Found in root (BTO:0001188). Cold MeOH extract of dried roots See: PubMed
Rubia yunnanensis (IPNI:765385-1) Found in root (BTO:0001188). Methanolic extract of air dried powdered roots See: PubMed
Eupatorium cannabinum subsp. asiaticum (NCBI:102770) Found in aerial part (BTO:0001658). MeOH extract of shade-dried, pulverized aerial parts,mixture of beta-sitosterol and stigmasterol See: PubMed
Citrus hystrix (NCBI:170989) Found in exocarp (BTO:0000733). The hexane extract of dried and ground fruit peels See: PubMed
Breynia fruticosa (NCBI:296042) Found in root (BTO:0001188). 90% Methanolic extract of air-dried, crushed roots. See: PubMed
Ficus mucuso (NCBI:309328) Found in fruit (BTO:0000486). Methanolic extract of air-dried and powdered figs(fruits) See: PubMed
Pisonia aculeata (NCBI:363212) Found in root (BTO:0001188). Cold MeOH extract of dried stems and roots, isolated as mixture of beta-setosterol & stigmasterol See: PubMed
Pisonia aculeata (NCBI:363212) Found in stem (BTO:0001300). Cold MeOH extract of dried stems and roots, isolated as mixture of beta-setosterol & stigmasterol See: PubMed
Lepisorus contortus (NCBI:699669) Found in whole plant (BTO:0001461). 95% EtOH extract of air-dried, powdered whole plant See: PubMed
Melia toosendan (NCBI:71608) Found in fruit (BTO:0000486). 95% ethanolic extract of dried fruits See: PubMed
Cordyceps sinensis (NCBI:72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
sterol methyltransferase inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of sterol methyltransferase.
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sitosterol (CHEBI:27693) has parent hydride stigmastane (CHEBI:26773)
sitosterol (CHEBI:27693) has role anticholesteremic drug (CHEBI:35821)
sitosterol (CHEBI:27693) has role antioxidant (CHEBI:22586)
sitosterol (CHEBI:27693) has role plant metabolite (CHEBI:76924)
sitosterol (CHEBI:27693) has role sterol methyltransferase inhibitor (CHEBI:52303)
sitosterol (CHEBI:27693) is a 3β-sterol (CHEBI:35348)
sitosterol (CHEBI:27693) is a phytosterols (CHEBI:26125)
Incoming β-sitosterol 3-O-acetate (CHEBI:69433) has functional parent sitosterol (CHEBI:27693)
β-sitosterol glucoside-3'-O-hexacosanoicate (CHEBI:66511) has functional parent sitosterol (CHEBI:27693)
daucosterol (CHEBI:67554) has functional parent sitosterol (CHEBI:27693)
sitoindoside I (CHEBI:67595) has functional parent sitosterol (CHEBI:27693)
stigmast-5-ene-3β,7α-diol (CHEBI:67594) has functional parent sitosterol (CHEBI:27693)
IUPAC Name
stigmast-5-en-3β-ol
Synonyms Sources
(-)-β-Sitosterol ChemIDplus
(24R)-ethylcholest-5-en-3β-ol UniProt
(24R)-Ethylcholest-5-en-3beta-ol ChemIDplus
(24R)-Stigmast-5-en-3beta-ol ChemIDplus
(3β)-Stigmast-5-en-3-ol ChemIDplus
22,23-Dihydrostigmasterol ChemIDplus
24α-Ethylcholesterol ChemIDplus
α-Dihydrofucosterol ChemIDplus
Azuprostat ChemIDplus
β-Sitosterin ChemIDplus
beta-Sitosterol KEGG COMPOUND
Cupreol ChemIDplus
Nimbosterol ChemIDplus
Sitosterol KEGG COMPOUND
Triastonal ChemIDplus
Database Links Databases
C00003672 KNApSAcK
C00023770 KNApSAcK
C01753 KEGG COMPOUND
D08518 KEGG DRUG
LMST01040129 LIPID MAPS
View more database links
Registry Numbers Types Sources
1916156 Beilstein Registry Number Beilstein
83-46-5 CAS Registry Number ChemIDplus
83-46-5 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
20525330 PubMed citation CiteXplore
23199991 PubMed citation CiteXplore
23215694 PubMed citation CiteXplore
23250922 PubMed citation CiteXplore
23266618 PubMed citation CiteXplore
23516045 PubMed citation CiteXplore
23624268 PubMed citation CiteXplore
Last Modified
29 June 2015