CHEBI:28824 - stigmasterol

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ChEBI Name stigmasterol
ChEBI ID CHEBI:28824
Definition A 3β-sterol that consists of 3β-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8195, CHEBI:26774
Supplier Information ChemicalBook:CB4333449, eMolecules:512178, Selleckchem:Stigmasterol(Stigmasterin), ZINC000004096712
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Wikipedia License
Stigmasterol – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.
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Formula C29H48O
Net Charge 0
Average Mass 412.69082
Monoisotopic Mass 412.37052
InChI InChI=1S/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey HCXVJBMSMIARIN-PHZDYDNGSA-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)\C=C\[C@@H](CC)C(C)C
Metabolite of Species Details
Eupatorium cannabinum subsp. asiaticum (NCBI:txid102770) Found in aerial part (BTO:0001658). MeOH extract of shade-dried, pulverized aerial parts,mixture of beta-sitosterol and stigmasterol See: PubMed
Pisonia aculeata (NCBI:txid363212) Found in stem (BTO:0001300). Cold MeOH extract of dried stems and roots, isolated as mixture of beta-setosterol & stigmasterol See: PubMed
Pisonia aculeata (NCBI:txid363212) Found in root (BTO:0001188). Cold MeOH extract of dried stems and roots, isolated as mixture of beta-setosterol & stigmasterol See: PubMed
Stemona curtisii (NCBI:txid492018) Found in root (BTO:0001188). 95% EtOH extract of dry, ground roots See: PubMed
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia, mixture of beta-sitosterol and stigmasterol See: PubMed
Roles Classification
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.
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ChEBI Ontology
Outgoing stigmasterol (CHEBI:28824) has parent hydride stigmastane (CHEBI:26773)
stigmasterol (CHEBI:28824) has role plant metabolite (CHEBI:76924)
stigmasterol (CHEBI:28824) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
stigmasterol (CHEBI:28824) is a 3β-sterol (CHEBI:35348)
stigmasterol (CHEBI:28824) is a phytosterols (CHEBI:26125)
stigmasterol (CHEBI:28824) is a stigmastane sterol (CHEBI:131703)
Incoming stigmasterol 3-O-β-D-glucoside (CHEBI:68383) has functional parent stigmasterol (CHEBI:28824)
stigmasterol 3-O-acetate (CHEBI:69434) has functional parent stigmasterol (CHEBI:28824)
delta7-stigmasterol (CHEBI:166889) is a stigmasterol (CHEBI:28824)
IUPAC Name
(22E)-stigmasta-5,22-dien-3β-ol
Synonyms Sources
(3β,22E)-stigmasta-5,22-dien-3-ol HMDB
5,22-Cholestadien-24-ethyl-3β-ol NIST Chemistry WebBook
β-stigmasterol NIST Chemistry WebBook
phytosterol NIST Chemistry WebBook
poriferasterol HMDB
stigmasta-5,22-dien-3β-ol NIST Chemistry WebBook
Stigmasterol KEGG COMPOUND
stigmasterol UniProt
Manual Xrefs Databases
C00003674 KNApSAcK
C00023774 KNApSAcK
C05442 KEGG COMPOUND
HMDB0000937 HMDB
LMST01040123 LIPID MAPS
Stigmasterol Wikipedia
View more database links
Registry Numbers Types Sources
2568182 Reaxys Registry Number Reaxys
83-48-7 CAS Registry Number KEGG COMPOUND
83-48-7 CAS Registry Number ChemIDplus
83-48-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
04 August 2021