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Entry
CA00324                                                            

Classification
Carotenoid Name
Diatoxanthin
IUPAC name (3R,3'R)-7,8-Didehydro-beta,beta-carotene-3,3'-diol
Formula
C40H54O2
Molecular Weight 
566.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective activity (Ref.429).
  • Xanthophyll cycle pigment.
  • Anticarcinogenic activity (Ref.494).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    11
    Isomers 
    InChI
    InChI=1S/C40H54O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-21,23,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
    InChIKey
    HNYJHQMUSVNWPV-DRCJTWAYSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C#CC1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C
    XLogP
    10.530
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.312
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    40.460 Å2
    Source organisms
    Pelagococcus subviridis (Ref.29) - Alga: Pelagophyceae
    Sarcinochrysis marina Getler (Ref.30) - Alga: Pelagophyceae
    Hymenomonas carterae (Ref.31) - Alga: Haptophyte
    Isochrysis galbana (Ref.31) - Alga: Haptophyte
    Pavlova lutheri (Ref.31) - Alga: Haptophyte
    Pavlova sp. (NEP)  - Alga: Haptophyte
    Phaeocystis sp. (Ref.31) - Alga: Haptophyte
    Prymnesium parvum (Ref.31) - Alga: Haptophyte
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
    Skeletonema costatum (Ref.36) - Alga: Diatom
    Skeletonema menzelii (Ref.36) - Alga: Diatom
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom
    Thalassiosira oceanica (Ref.36) - Alga: Diatom
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom
    Thalassiosira rotula (Ref.36) - Alga: Diatom
    Grammatophora oceanica (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Nitzschia sp. (Ref.36) - Alga: Diatom
    Phaeodactylum tricornutum (Ref.36) - Alga: Diatom
    Euglena gracilis (Ref.38, Ref.8) - Alga: Euglenoid
    Euglena sanguinea (Ref.43) - Alga: Euglenoid
    Euglena viridis (Ref.44) - Alga: Euglenoid
    Eutreptiella gymnastica (Ref.45) - Alga: Euglenoid
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Carassius auratus (Ref.365) - Bony fish: gold fish
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell
    Clione limacina (Ref.635) - gastropods
    Paedoclione doliiformis (Ref.635) - gastropods
    Limacina helicina (Ref.635) - gastropods
    References
  • Ref.29 : T.Bjoernland, S. Liaaen-Jensen, and J. Throndsen, Phytochemistry, Vol. 28, No. 12, pp. 3347-3353, 1989; "Carotenoids of the marine chrysophyte Pelagococcus subviridis".
  • 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.33 : J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.494 : Takashi MAOKA, Miyuki TSUSHIMA, and Hoyoku NISHINO, Chem. Pharm. Bull. 50(12) 1630—1633 (2002), "Isolation and Characterization of Dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes".
  • Ref.34 : R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • 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.38 : D. V. Heelis, W. Kernick, G. O. Philips, and K. Davies, Arch. Microbiol. 121, 207-211 (1979), "Separation and Identification of the Carotenoid Pigments of Stigmata Isolated from Light Grown Cells of Euglena gracilis Strain Z".
  • Ref.8 : L. Schlueter, T. L. Lauridsen, G. Krogh, and Joergensen, Freshwater Biology, 2006, 51, 1474-1485 " Identification and quantification of phytoplankton groups in lakes using new pigment ratios – a comparison between pigment analysis by HPLC and microscopy".
  • Ref.43 : Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".
  • Ref.44 : A. Fiksdahl, S. Liaaen-Jensen, Phytochemistry, Vol.27, No.5, pp. 1447 - 1450, 1988 "Diacetylenic carotenoids from Euglena viridis".
  • Ref.45 : A. Fiksdahl, T. Bjoernland, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No.3, pp. 649-655, 1984, "Algal carotenoids with novel end groups".
  • 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.365 : Masahiro Ohkubo, Miyuki Tsushima, Takashi Maoka, Takao Matsuno, Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, Volume 124, Issue 3, November 1999, Pages 333–340, "Carotenoids and their metabolism in the goldfish Carassius auratus (Hibuna)".
  • Ref.442 : Kiyoshi Katagiri, Takashi Maoka, Takao Matsuno, COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. B, COMPARATIVE BIOCHEMISTRY, 84(4):473-476 · JANUARY 1986, "Carotenoids of shell fishes-VIII. Comparative biochemical studies of carotenoids in three species of spindleshell, Fusinus perplexus, F.p. ferrugineus and F. forceps".
    .
  • Ref.429 : Reimund Goss, Elizabeth Ann Pinto, Christian Wilhelm, Michael Richter, Journal of Plant Physiology, Volume 163, Issue 10, 5 October 2006, Pages 1008–1021, "The importance of a highly active and ΔpH-regulated diatoxanthin epoxidase for the regulation of the PS II antenna function in diadinoxanthin cycle containing algae".
  • CAS
    31063-73-7
    Links to other DB
    KNApSAcK: C00022863
    LipidBank: VCA0052
    MassBank: CA000052

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