Structure Database (LMSD)

Common Name
fucoxanthin
Systematic 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
  • (3'S,5'R,6'R)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one
  • (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-beta,beta-carotene
  • Fucoxanthin
LM ID
LMPR01070300
Formula
C42H58O6
Exact Mass
Calculate m/z
658.423341
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C40 isoprenoids (tetraterpenes) [PR0107]

Biological Context

Fucoxanthin is a carotenoid that occurs naturally in certain algae. It significantly reduces abdominal white adipose tissue (WAT) in mice and rats when included in their diet.1 Fucoxanthin increases the amount of mitochondrial uncoupling protein 1 (UCP1), a fatty acid-stimulated protein involved in respiration and thermogenesis in WAT of mice and rats.1 In KK-Ay mice, which are used to model obese type 2 diabetics with hyperinsulinemia, fucoxanthin reduces WAT gain and also decreases blood glucose and plasma insulin levels.1,2

This information has been provided by Cayman Chemical

References

1. Maeda, H., Hosokawa, M., Sashima, T., et al. Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues. Biochem. Biophys. Res. Commun. 332(2), 392-397 (2005).
2. Chen, J.K., Chen, J., Imig, J.D., et al. Identification of novel endogenous cytochrome p450 arachidonate metabolites with high affinity for cannabinoid receptors. J. Biol. Chem. 283(36), 24514-24524 (2008).
Cayman Chemical

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Phaeophyceae (#2870)
1D and 2D NMR Study of Some Allenic Carotenoids of the Fucoxanthin Series,
Mag Reson Chem, 1990

String Representations

InChiKey (Click to copy)
SJWWTRQNNRNTPU-XJUZQKKNSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C(C(=O)/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C([H])=[C@@]=C1[C@@](O)(C)C[C@@H](OC(=O)C)CC1(C)C)\C)[C@]12C(C)(C)C[C@H](O)C[C@@]1(C)O2

Other Databases

Wikipedia
fucoxanthin
KEGG ID
C08596
CHEBI ID
5186
PubChem CID
5281239
Cayman ID
13068
Carotenoid ID
CA00519
PDB ID
A86

Calculated Physicochemical Properties

Heavy Atoms 48
Rings 3
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 721.78
Topological Polar Surface Area 96.36
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 6
logP 10.12
Molar Refractivity 196.66

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Created at
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Updated at
11th Mar 2025