CHEBI:3168 - brassicasterol

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ChEBI Name brassicasterol
ChEBI ID CHEBI:3168
Definition An 3β-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3β. It is a phytosterol found in marine algae, fish, and rapeseed oil.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9336283, eMolecules:480445, ZINC000000967928
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2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.
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Formula C28H46O
Net Charge 0
Average Mass 398.675
Monoisotopic Mass 398.35487
InChI InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
InChIKey OILXMJHPFNGGTO-ZAUYPBDWSA-N
SMILES [C@@]12([C@]3([C@@]([C@@]4(C(C[C@@H](O)CC4)=CC3)C)(CC[C@@]1([C@@]([C@@H](/C=C/[C@@H](C(C)C)C)C)(CC2)[H])C)[H])[H])[H]
Metabolite of Species Details
Chloromorum sp. toxicum (NCBI:txid299907) See: PubMed
Schisandra chinensis (NCBI:txid50507) Found in fruit (BTO:0000486). See: PubMed
Salmo salar (NCBI:txid8030) See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: PubMed
Roles Classification
Biological Role(s): EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor
An EC 1.3.1.* (oxidoreductase acting on donor CH-CH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of Delta24-sterol reductase (EC 1.3.1.72).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
sterol biosynthesis inhibitor
Any compound that inhibits the biosynthesis of any sterol.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
Application(s): biomarker
A substance used as an indicator of a biological state.
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ChEBI Ontology
Outgoing brassicasterol (CHEBI:3168) has role algal metabolite (CHEBI:84735)
brassicasterol (CHEBI:3168) has role animal metabolite (CHEBI:75767)
brassicasterol (CHEBI:3168) has role biomarker (CHEBI:59163)
brassicasterol (CHEBI:3168) has role EC 1.3.1.72 (Δ24-sterol reductase) inhibitor (CHEBI:78728)
brassicasterol (CHEBI:3168) has role human metabolite (CHEBI:77746)
brassicasterol (CHEBI:3168) has role marine metabolite (CHEBI:76507)
brassicasterol (CHEBI:3168) has role plant metabolite (CHEBI:76924)
brassicasterol (CHEBI:3168) has role sterol biosynthesis inhibitor (CHEBI:83317)
brassicasterol (CHEBI:3168) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
brassicasterol (CHEBI:3168) is a 3β-sterol (CHEBI:35348)
brassicasterol (CHEBI:3168) is a ergostanoid (CHEBI:50403)
brassicasterol (CHEBI:3168) is a phytosterols (CHEBI:26125)
Incoming brassicasterol 3-β-D-glucoside (CHEBI:145041) has functional parent brassicasterol (CHEBI:3168)
IUPAC Name
(22E)-ergosta-5,22-dien-3β-ol
Synonyms Sources
(22E,24R)-24-methylcholesta-5,22-dien-3β-ol ChEBI
(3β,22E)-ergosta-5,22-dien-3-ol ChEBI
24(R)-methylcholesta-5,22E-dien-3β-ol HMDB
24-methyl cholest-5,22-dien-3β-ol ChEBI
brassicasterin NIST Chemistry WebBook
brassicasterol UniProt
ergosta-5,22(E)-dien-3β-ol ChemIDplus
ergosta-5,22E-dien-3β-ol HMDB
Manual Xrefs Databases
Brassicasterol Wikipedia
C00003646 KNApSAcK
C08813 KEGG COMPOUND
CPD-4161 MetaCyc
FDB012496 FooDB
HMDB0011181 HMDB
LMST01030098 LIPID MAPS
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Registry Numbers Types Sources
474-67-9 CAS Registry Number KEGG COMPOUND
474-67-9 CAS Registry Number NIST Chemistry WebBook
474-67-9 CAS Registry Number ChemIDplus
Citations Types Sources
11319028 PubMed citation Europe PMC
12162789 PubMed citation Europe PMC
15489546 PubMed citation Europe PMC
21585343 PubMed citation Europe PMC
29397797 PubMed citation Europe PMC
30259993 PubMed citation Europe PMC
30390455 PubMed citation Europe PMC
30853340 PubMed citation Europe PMC
30857717 PubMed citation Europe PMC
31255261 PubMed citation Europe PMC
31374906 PubMed citation Europe PMC
Last Modified
17 January 2023