CHEBI:5186 - fucoxanthin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fucoxanthin
ChEBI ID CHEBI:5186
Definition An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:67925
Supplier Information
Download Molfile XML SDF
Formula C42H58O6
Net Charge 0
Average Mass 658.90632
Monoisotopic Mass 658.423
InChI InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1
InChIKey SJWWTRQNNRNTPU-XJUZQKKNSA-N
SMILES [H]C(=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(C)=O)C(\C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C(=O)C[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C
Metabolite of Species Details
Sargassum siliquastrum (NCBI:txid127572) See: PubMed
Phaeodactylum tricornutum (NCBI:txid2850) See: PubMed
Cystoseira barbata (NCBI:txid590725) See: PubMed
Sargassum fusiforme (NCBI:txid590727) See: PubMed
Undaria pinnatifida (NCBI:txid74381) See: PubMed
Himanthalia elongata (NCBI:txid74478) See: PubMed
Saccharina japonica (NCBI:txid88149) See: PubMed
Sporochnus comosus (NCBI:txid45367) CH2Cl2 extract of freeze-dried brown algae See: PubMed
Roles Classification
Chemical Role(s): food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
Biological Role(s): 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.
CFTR potentiator
A membrane transport modulator that restores the chloride ion transport ability of defective cystic fibrosis transmembrane conductance regulator (CFTR) genes.
food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
Application(s): food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
hypoglycemic agent
A drug which lowers the blood glucose level.
hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fucoxanthin (CHEBI:5186) has role algal metabolite (CHEBI:84735)
fucoxanthin (CHEBI:5186) has role apoptosis inhibitor (CHEBI:68494)
fucoxanthin (CHEBI:5186) has role CFTR potentiator (CHEBI:66902)
fucoxanthin (CHEBI:5186) has role food antioxidant (CHEBI:77962)
fucoxanthin (CHEBI:5186) has role hepatoprotective agent (CHEBI:62868)
fucoxanthin (CHEBI:5186) has role hypoglycemic agent (CHEBI:35526)
fucoxanthin (CHEBI:5186) has role marine metabolite (CHEBI:76507)
fucoxanthin (CHEBI:5186) has role neuroprotective agent (CHEBI:63726)
fucoxanthin (CHEBI:5186) has role plant metabolite (CHEBI:76924)
fucoxanthin (CHEBI:5186) is a acetate ester (CHEBI:47622)
fucoxanthin (CHEBI:5186) is a allenes (CHEBI:37602)
fucoxanthin (CHEBI:5186) is a epoxycarotenol (CHEBI:35307)
fucoxanthin (CHEBI:5186) is a secondary alcohol (CHEBI:35681)
fucoxanthin (CHEBI:5186) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(3S,5R,6S,3'S,5'R,6'R)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6-epoxy-5,6,7,8,5',6'-hexahydro-β,β-caroten-3'-yl acetate
Synonyms Sources
(3'S,5'R,6'R)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-β,β-caroten-8-one CBN
(3S,3'S,5R,5'R,6S,6'R)-3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-β,β-carotene ChemIDplus
Fucoxanthin KEGG COMPOUND
Manual Xrefs Databases
C00003773 KNApSAcK
C08596 KEGG COMPOUND
LMPR01070300 LIPID MAPS
View more database links
Registry Numbers Types Sources
3351-86-8 CAS Registry Number KEGG COMPOUND
3351-86-8 CAS Registry Number ChemIDplus
6580822 Beilstein Registry Number Beilstein
6580822 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16786166 PubMed citation Europe PMC
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28850007 PubMed citation Europe PMC
28865626 PubMed citation Europe PMC
28928905 PubMed citation Europe PMC
Last Modified
04 October 2017
General Comments
2006-04-04 The name 'fucoxanthin' is also applied in the 1974 CBN carotenoid recommendations to the all-trans but otherwise non-stereochemically defined compound.
2006-04-04 The existence of the 6'S stereoisomer has also been reported [Liaaen-Jensen,S. (1997), Pure Appl. Chem., 69, 2027-2038].