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Entry
CA00384                                                            

Classification
Carotenoid Name
Zeaxanthin diglucoside
IUPAC name (3R,3'R)-3,3'-Di(beta-D-glucopyranosyloxy)-beta,beta-carotene
Formula
C52H76O12
Molecular Weight 
893.128 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
  • Constitutional isomer: CA00127, CA00945, CA00964
  • InChI
    InChI=1S/C52H76O12/c1-31(17-13-19-33(3)21-23-39-35(5)25-37(27-51(39,7)8)61-49-47(59)45(57)43(55)41(29-53)63-49)15-11-12-16-32(2)18-14-20-34(4)22-24-40-36(6)26-38(28-52(40,9)10)62-50-48(60)46(58)44(56)42(30-54)64-50/h11-24,37-38,41-50,53-60H,25-30H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,31-15+,32-16+,33-19+,34-20+/t37-,38-,41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m1/s1
    InChIKey
    DHNSFMNURMJEQV-OIBMWOCGSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](O[C@@H]2CC(=C(C(C2)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C)C[C@H](CC2(C)C)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)\C)\C)/C)/C)C)[C@@H]([C@H]([C@@H]1O)O)O
    XLogP
    8.348
    Hydrogen Bond donors
    (Lipinski's definition)
    8
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    12
    LipinskiFailures
    4
    Complexity of molecule
    0.314
    Number of heavy atoms
    64
    TPSA
    (Topological Polar Surface Area) 
    198.760 Å2
    Source organisms
    Sulfolobus shibatae (Ref.330) - Archaea: Crenarchaeota
    Thermus thermophilus (Ref.435) - Deinococcus-Thermus: Thermophilic bacterium
    References
  • Ref.330 : Kull, Daniel R.; Pfander, Hanspeter, Journal of Natural Products¬†(1997),¬†60(4),¬†371-374., "Isolation and Structure Elucidation of Carotenoid Glycosides from the Thermoacidophilic Archaea Sulfolobus shibatae".
  • Ref.435 : Yokoyama A, Shizuri Y, Hoshino T, Sandmann G., Arch Microbiol. 1996 May 22;165(5):342-5., "Thermocryptoxanthins: novel intermediates in the carotenoid biosynthetic pathway of Thermus thermophilus".
  • CAS
    53762-00-8
    Links to other DB
    KNApSAcK: C00000932
    LipidBank: VCA1017

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