Carotenoids obi
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Carotenoid Name
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
Molecular Weight 
616.848 g/mol
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)
  • Constitutional isomer: CA01077, CA00424, CA00512, CA00650, CA01080, CA01081
  • InChI
    Canonical SMILES
    Hydrogen Bond donors
    (Lipinski's definition)
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    Complexity of molecule
    Number of heavy atoms
    (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
  • 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
    Links to other DB
    KNApSAcK: C00023240
    LipidBank: VCA0053
    MassBank: CA000151

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