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Entry
CA00404                                                            

Classification
Carotenoid Name
Diadinoxanthin;
Diadinoxanthin A
IUPAC name (3S,5R,6S,3'R)-5,6-Epoxy-7',8'-didehydro-5,6-dihydro-beta,beta-caroten-3,3'-diol
Formula
C40H54O3
Molecular Weight 
582.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective activity (Ref.429).
  • Photosynthetic pigment (Ref.429).
  • Xanthophyll cycle pigment.
  • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    10
    Isomers 
    InChI
    InChI=1S/C40H54O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-20,23-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
    InChIKey
    OGHZCSINIMWCSB-GHIQLMQGSA-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/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    9.730
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    52.990 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
    Gonyostomum semen (Ref.35) - Alga: Raphidophyceae
    Vacuolaria virescens (Ref.35) - Alga: Raphidophyceae
    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
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate
    Rhinogobius brunneus (Ref.290) - Bony fish: Amur goby
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Solorina crocea (Ref.374) - Fungi: lichen
    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.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.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.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.290 : Miyuki Tsushima ,Eisaku Mune , Takashi Maoka , and Takao Matsuno, J. Nat. Prod., 2000, 63 (7), pp 960–964, "Prev. Article Next Article Table of Contents Isolation of Stereoisomeric Epoxy Carotenoids and New Acetylenic Carotenoid from the Common Freshwater Goby Rhinogobius brunneus".
  • 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.635 : Takashi Maoka, Takashi Kuwahara, and Masanao Narita, Mar. Drugs 2014, 12, 1460-1470, "Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain", doi:10.3390/md12031460.
  • 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
    18457-54-0
    Links to other DB
    KNApSAcK: C00022941

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