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Entry
CA00277                                                            

Classification
Carotenoid Name
4-Ketomyxoxanthophyll;
4-Keto-myxol-2'-methylpentoside;
P483
IUPAC name (3S,2'S)-3,1'-Dihydroxy-2'-methylpentosyloxy-3',4'-didehydro-1',2'-dihydro-beta,psi-caroten-4-one
Formula
C46H64O8
Molecular Weight 
744.972 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including one ketone (13 in total)
Number of
conjugated multiple bonds 
13 including one ketone (13 in total)
Isomers 
  • Constitutional isomer: CA00276, CA00963, CA00523
  • InChI
    InChI=1S/C46H64O8/c1-30(17-12-13-18-31(2)20-15-23-33(4)25-27-37-35(6)40(48)38(47)29-45(37,8)9)19-14-21-32(3)22-16-24-34(5)26-28-39(46(10,11)52)54-44-43(51)42(50)41(49)36(7)53-44/h12-28,36,38-39,41-44,47,49-52H,29H2,1-11H3/b13-12+,19-14+,20-15+,22-16+,27-25+,28-26+,30-17+,31-18+,32-21+,33-23+,34-24+/t36?,38-,39-,41?,42?,43?,44?/m0/s1
    InChIKey
    GYSHFNPXXPCKGU-AJGWADBESA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C=C(/C=C/[C@@H](C(O)(C)C)OC1OC(C)C(C(C1O)O)O)\C)\C
    XLogP
    9.539
    Hydrogen Bond donors
    (Lipinski's definition)
    5
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.305
    Number of heavy atoms
    54
    TPSA
    (Topological Polar Surface Area) 
    136.680 Å2
    Source organisms
    Oscillatoria limosa (Ref.1) - Cyanobacteria
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria
    Anabaena flos-aquae (Ref.1, Ref.611) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae
    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.611 : H Züllig - Limnology and Oceanography, Volume 26, Issue 5, September 1981, Pages 970–976DOI: 10.4319/lo.1981.26.5.0970, "On the use of carotenoid stratigraphy in lake sediments for detecting past developments of phytoplankton".
  • CAS
    -
    Links to other DB

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