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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   
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
    InChI=1S/C40H56O5/c1-28(17-13-18-30(3)21-22-35-36(5,6)23-32(41)25-38(35,9)44)15-11-12-16-29(2)19-14-20-31(4)34(43)27-40-37(7,8)24-33(42)26-39(40,10)45-40/h11-21,32-33,41-42,44H,23-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t22-,32-,33-,38+,39+,40-/m0/s1
    InChIKey
    NZEPSBGUXWWWSI-VOPPYBPXSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)\C
    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
    Source organisms
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Pavlova sp. (NEP)  - Alga: Haptophyte
    Chattonella japonica (Ref.35) - Alga: Raphidophyceae
    Fibrocapsa japonica (Ref.35) - Alga: Raphidophyceae
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom
    Thalassiosira rotula (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Fucus serratus (Ref.53) - Brown alga: Fucaceae
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae
    Laminaria digitata (Ref.53);Corbicula japonica  - 
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Solorina crocea (Ref.374) - Fungi: lichen
    Echinoidea sp. (Ref.375) - Sea urchin
    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, Valérie 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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