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Entry
CA00230                                                            

Classification
Carotenoid Name
Myxol 2'-rhamnoside;
Myxoxanthophyll
IUPAC name (3R,2'S)-2'-(alpha-L-Rhamnosyloxy)-3',4'-didehydro-1',2'-dihydro-beta,psi-carotene-3,1'-diol
Formula
C46H66O7
Molecular Weight 
730.988 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective pigment - possible outer membrane-bound UV-B photoprotector (Ref.497).
  • Number of
    conjugated double bonds 
    12
    Number of
    conjugated multiple bonds 
    12
    Isomers 
  • Constitutional isomer: CA00103, CA00946, CA00961, CA00212, CA00240, CA00211, CA00269, CA00561
  • InChI
    InChI=1S/C46H66O7/c1-31(17-12-13-18-32(2)20-15-23-34(4)25-27-39-36(6)29-38(47)30-45(39,8)9)19-14-21-33(3)22-16-24-35(5)26-28-40(46(10,11)51)53-44-43(50)42(49)41(48)37(7)52-44/h12-28,37-38,40-44,47-51H,29-30H2,1-11H3/b13-12+,19-14+,20-15+,22-16+,27-25+,28-26+,31-17+,32-18+,33-21+,34-23+,35-24+/t37-,38+,40-,41-,42+,43+,44+/m0/s1
    InChIKey
    MUCOHWBULSBLLZ-AUWWDLDMSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C=C(/C=C/[C@@H](C(O)(C)C)O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)\C)\C
    XLogP
    9.973
    Hydrogen Bond donors
    (Lipinski's definition)
    5
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    2
    Complexity of molecule
    0.303
    Number of heavy atoms
    53
    TPSA
    (Topological Polar Surface Area) 
    119.610 Å2
    Source organisms
    Oscillantoria rubescens (Ref.1) - Cyanobacteria: other name is Planktothrix rubescens
    Oscillatoria agardhii (Ref.1) - Cyanobacteria: other name is Planktothrix agardhii
    Oscillatoria amoena (Ref.1) - Cyanobacteria
    Oscillatoria tenuis (Ref.1) - Cyanobacteria: hot spring alga
    Oscillatoria princeps (Ref.1) - Cyanobacteria
    Arthrospira sp. (Ref.1) - Cyanobacteria
    Phormidium foveolarum (Ref.1) - Cyanobacteria
    Phormidium lucidum (Ref.1) - Cyanobacteria
    Microcoleus paludosus (Ref.1) - Cyanobacteria
    Microcoleus vaginatus (Ref.1, Ref.5) - Cyanobacteria
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria
    Anabaena cylindrica (Ref.1, Ref.5) - Cyanobacteria: a nitrogen-fixing filamentous cyanobacterium
    Anabaena variabilis (Ref.1, Ref.5) - Cyanobacteria: filamentous cyanobacterium
    Anabaena aerulosa oscillatorioides (Ref.1) - Cyanobacteria
    Anabaena flos-aquae (Ref.1) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae
    Cylindrospormum sp. (Ref.1, Ref.5) - Cyanobacteria
    Nostoc sp. (Ref.1, Ref.5) - Cyanobacteria
    Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad
    Tolypothrix tenuis (Ref.1) - Cyanobacteria: filaments repeated single false branched forming cyanobacteria, yellow-brown colored
    Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream
    Mastigocladus laminosus (Ref.1, Ref.5) - Cyanobacteria
    Coccochloris elabens (Ref.1, Ref.5) - Cyanobacteria
    Synechococcus elongatus (Ref.1) - Cyanobacteria: freshwater unicellular cyanobacterium
    Microcystis aeruginosa (Ref.1) - Cyanobacteria
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular
    Synechocystis sp. (Ref.8) - Cyanobacteria
    Aphanizomenon gracile (Ref.8) - Cyanobacteria
    Planktothrix agardhii (Ref.8) - Cyanobacteria
    Microcystis aeruginosa (Ref.8) - Cyanobacteria
    References
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.5 : T. W. Goodwin, J. gen. Microbiol. 17, 467-473 (1957), "The nature and distribution of Carotenoids in some Blue-Green Algae".
  • 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.497 : Ehling-Schulz, Bilger W, Scherer S., J Bacteriol. 1997 Mar;179(6):1940-5., "UV-B-induced synthesis of photoprotective pigments and extracellular polysaccharides in the terrestrial cyanobacterium Nostoc commune.".
  • CAS
    11004-68-5
    Links to other DB
    ProCarDB: C1814

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