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CHEBI:3168 - brassicasterol

ChEBI IDCHEBI:3168
ChEBI Namebrassicasterol
Stars
DefinitionAn 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.
Last Modified17 January 2023
DownloadsMolfile
FormulaC28H46O
Net Charge0
Average Mass398.675
Monoisotopic Mass398.35487
SMILES[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)/C=C/[C@H](C)C(C)C
InChIInChI=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
InChIKeyOILXMJHPFNGGTO-ZAUYPBDWSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Chloromorum sp. toxicum (ncbitaxon:299907) - PubMed (18620714)
Homo sapiens (ncbitaxon:9606) blood serum (BTO:0000133) PubMed (15489546)
Salmo salar (ncbitaxon:8030) - PubMed (29397797)
Schisandra chinensis (ncbitaxon:50507) fruit (BTO:0000486) PubMed (30853340)
Roles Classification
Biological Roles:
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 Δ24-sterol reductase (EC 1.3.1.72).
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
sterol biosynthesis inhibitor  Any compound that inhibits the biosynthesis of any sterol.
Application:
biomarker  A substance used as an indicator of a biological state.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
brassicasterol 3-β-D-glucoside (CHEBI:145041) has functional parent brassicasterol (CHEBI:3168)
IUPAC Name 
(22E)-ergosta-5,22-dien-3β-ol
Synonyms  Source
(22E,24R)-24-methylcholesta-5,22-dien-3β-olChEBI
24(R)-methylcholesta-5,22E-dien-3β-olHMDB
24-methyl cholest-5,22-dien-3β-olChEBI
(3β,22E)-ergosta-5,22-dien-3-olChEBI
brassicasterinNIST Chemistry WebBook
ergosta-5,22E-dien-3β-olHMDB
UniProt Name  Source
brassicasterolUniProt
Manual XrefsDatabases
BrassicasterolWikipedia
C00003646KNApSAcK
C08813KEGG COMPOUND
CPD-4161MetaCyc
FDB012496FooDB
HMDB0011181HMDB
LMST01030098LIPID MAPS
Registry NumbersSources
CAS:474-67-9ChemIDplus
CAS:474-67-9NIST Chemistry WebBook
CAS:474-67-9KEGG COMPOUND
Citations