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Entry
CA00513                                                            
Classification
Carotenoid Name
Fucoxanthinol
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3,3',5'-trihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one
Formula
C40H56O5
Molecular Weight 
616.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antiproliferative activity in various cancer cells by downregulating anti-apoptotic proteins and cell cycly regulators: Bcl2, Bcl-xL, XIAP, survivin, p-caspase-9, cyclin D1, cyclin D2, CDK4, CDK6, c-myc and ppRb (Ref.493).
  • Cell cycle arrest during G1 phase, up-regulation of PARP cleavage, caspase-3, -8 and -9 cleavage, silencing of NF-κB, AP-1and PI3K/Akt pathways and proteins proteasome degradation (Ref.493).
  • Anti-obese activity stronger than that of Fucoxanthin -suppressive effects on lipid accumulation and decreased glycerol-3-phosphate dehydrogenase activity (Ref.514).
    • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
    Isomers 
  • Constitutional isomer: CA01077, CA00424, CA00512, CA00650, CA01080, CA01081
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    9.134
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.307
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    90.290 Å2
    Reaction
  • Substrate: CR00138,  CR00173,  CR00282,  CR00387
  • Product: CR00293
    • Pathway
  • Pathway: CB000067,  CB000068,  CB000070,  CB000093,  CB000094,  CB000143
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae ((Stramenopiles) - Chromulinaceae)
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae ((Stramenopiles) - Ochromonadaceae)
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles ((Stramenopiles) - Unclassified stramenopiles)
    Navicula pelliculosa (Ref.36) - Alga: Diatom (Bacillariophyta - Naviculaceae)
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Thalassiosira rotula (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus serratus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Laminaria digitata (Ref.53) - Brown alga: Laminariaceae ((Phaeophyceae) - Laminariaceae)
    Chattonella japonica (Ref.35) - Alga: Raphidophyceae ((Raphidophyceae) - Chattonellaceae)
    Fibrocapsa japonica (Ref.35) - Alga: Raphidophyceae ((Raphidophyceae) - Chattonellaceae)
    Solorina crocea (Ref.374) - Fungi: lichen (Ascomycota - Peltigeraceae)
    Corbicula clams (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula japonica (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula sandai (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Echinoidea sp. (Ref.375) - Sea urchin (Echinodermata - Unclassified Echinodermata)
    References
  • Ref.30: N. W. Withers, A. Fiksdahl, R.C. Tuttle, and S. Liaaen-Jense, Comp. Biochem. Physiol. Vol. 68B, pp. 345 to 349, 1979, "Carotenoids of the Chrysophyceae".
  • Ref.31: R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.35: A.Fiksdahl, N. Withers, R. R. L. Guillard, and S. Liaaen-Jensen, Comp. Biochem. Physiol. Vol. 78B, No. 1, pp. 265-271, 1984, "Carotenoids of the Raphidophyceae - a chemosystematic contribution ".
  • Ref.36: F. Pennington, R. R. L. Guillard and S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol.16, No.7/8, pp. 589-592, 1988, "Carotenoid Distribution Patterns in Bacillariophyceae (Diatoms)".
  • Ref.53: G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • Ref.221: Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.374: Czeczuga, Bazyli; Olech, Maria, Phyton (Horn, Austria) (1990), 30(2), 235-45., "Investigations on carotenoids in lichens. XXV. Studies of carotenoids in lichens from Spitsbergen".
  • Ref.375: Galasko, Gail; Hora, J.; Toube, T. P.; Weedon, B. C. L.; Andre, D.; Barbier, M.; Lederer, E.; Villanueva, V. R., Journal of the Chemical Society [Section] C: Organic (1969), (9), 1264-5., "Carotenoids and related compounds. XXII. Allenic carotenoids in sea urchins".
  • Ref.493: Anne-Laure Gagez, ValĂ©rie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • Ref.514: Hayato Maeda, Masashi Hosokawa, Tokutake Sashima, Nobuyuki Takahashi, Teruo Kawada, Kazuo Miyashita, International Journal of Molecular Medicine, Volume 18, Issue 1, ISSN:1791-244X, "Fucoxanthin and its metabolite, fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells".
    • CAS
    7176-02-5
    Links to other DB
    KNApSAcK: C00023240
    LipidBank: VCA0053
    MassBank: CA000151

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