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Entry
CA00388                                                            

Classification
Carotenoid Name
Thermozeaxanthin-15;
Zeaxanthin glucoside ester
IUPAC name (3R,3'R)-3'-[(6-O-13-Methyltetradecanoyl-b-D-glucopyranosyl)oxy]-beta,beta-caroten-3-ol
Formula
C61H94O8
Molecular Weight 
955.362 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Membrane stabilizer in large unilamellar liposomes (LUVs) of thermophilic bacterium, Thermus thermophilus in acidic conditions (Ref.504, Ref.505).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
    InChI
    InChI=1S/C61H94O8/c1-43(2)26-20-18-16-14-13-15-17-19-21-33-55(63)67-42-54-56(64)57(65)58(66)59(69-54)68-51-39-49(8)53(61(11,12)41-51)37-35-47(6)32-25-30-45(4)28-23-22-27-44(3)29-24-31-46(5)34-36-52-48(7)38-50(62)40-60(52,9)10/h22-25,27-32,34-37,43,50-51,54,56-59,62,64-66H,13-21,26,33,38-42H2,1-12H3/b23-22+,29-24+,30-25+,36-34+,37-35+,44-27+,45-28+,46-31+,47-32+/t50-,51-,54-,56-,57+,58-,59-/m1/s1
    InChIKey
    GUHDWRQBJQZYHJ-UXVUJNRNSA-N
    Canonical SMILES
    CC(CCCCCCCCCCCC(=O)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)\C)/C)/C)C)[C@@H]([C@H]([C@@H]1O)O)O)C
    XLogP
    16.787
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.227
    Number of heavy atoms
    69
    TPSA
    (Topological Polar Surface Area) 
    125.680 Å2
    Source organisms
    Thermus thermophilus (Ref.435) - Deinococcus-Thermus: Thermophilic bacterium
    References
  • 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".
  • Ref.504 : Hara M, Yuan H, Yang Q, Hoshino T, Yokoyama A, Miyake J., PMID: 10556496, Volume 1461, Issue 1, 9 November 1999, Pages 147–154, “Stabilization of liposomal membranes by thermozeaxanthins: carotenoid-glucoside esters”.
  • Ref.505 : Yuan HQ, Cong LH, Hara M, Hoshino T, Yokoyama A, Miyake J., Sheng Wu Hua Xue Yu Sheng Wu Wu Li Xue Bao (Shanghai). 2001;33(5):577-581., PMID: 12040403, "Effect of Thermozeaxanthins on Liposome Membranes in Acidic and Basic Conditions.".
  • CAS
    165525-69-9
    Links to other DB
    KEGG COMPOUND: C15983
    LipidBank: VCA1026
    ProCarDB: C0861

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