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Entry
CA00386                                                            

Classification
Carotenoid Name
Thermozeaxanthin-13;
Zeaxanthin glucoside ester
IUPAC name (3R,3'R)-3'-[(6-O-11-Methyldodecanoyl-b-D-glucopyranosyl)oxy]-beta,beta-caroten-3-ol
Formula
C59H90O8
Molecular Weight 
927.31 g/mol
Structure      Search similar carotenoids

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/C59H90O8/c1-41(2)24-18-16-14-13-15-17-19-31-53(61)65-40-52-54(62)55(63)56(64)57(67-52)66-49-37-47(8)51(59(11,12)39-49)35-33-45(6)30-23-28-43(4)26-21-20-25-42(3)27-22-29-44(5)32-34-50-46(7)36-48(60)38-58(50,9)10/h20-23,25-30,32-35,41,48-49,52,54-57,60,62-64H,13-19,24,31,36-40H2,1-12H3/b21-20+,27-22+,28-23+,34-32+,35-33+,42-25+,43-26+,44-29+,45-30+/t48-,49-,52-,54-,55+,56-,57-/m1/s1
    InChIKey
    HHINJQKIQDURLW-XFMDTAGXSA-N
    Canonical SMILES
    CC(CCCCCCCCCC(=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
    15.649
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.236
    Number of heavy atoms
    67
    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
    165525-68-8
    Links to other DB
    KEGG COMPOUND: C15983
    LipidBank: VCA1025
    ProCarDB: C0859

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