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Entry
CA00389                                                            

Classification
Carotenoid Name
Thermozeaxanthin-17;
Zeaxanthin glucoside ester
IUPAC name (3R,3'R)-3'-[(6-O-15-Methylhexadecanoyl-b-D-glucopyranosyl)oxy]-beta,beta-caroten-3-ol
Formula
C63H98O8
Molecular Weight 
983.414 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/C63H98O8/c1-45(2)28-22-20-18-16-14-13-15-17-19-21-23-35-57(65)69-44-56-58(66)59(67)60(68)61(71-56)70-53-41-51(8)55(63(11,12)43-53)39-37-49(6)34-27-32-47(4)30-25-24-29-46(3)31-26-33-48(5)36-38-54-50(7)40-52(64)42-62(54,9)10/h24-27,29-34,36-39,45,52-53,56,58-61,64,66-68H,13-23,28,35,40-44H2,1-12H3/b25-24+,31-26+,32-27+,38-36+,39-37+,46-29+,47-30+,48-33+,49-34+/t52-,53-,56-,58-,59+,60-,61-/m1/s1
    InChIKey
    NYTQKXXVJXMQSW-DSSRBQPMSA-N
    Canonical SMILES
    CC(CCCCCCCCCCCCCC(=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
    17.925
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.219
    Number of heavy atoms
    71
    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
    165525-70-2
    Links to other DB
    KEGG COMPOUND: C15983
    LipidBank: VCA1027
    ProCarDB: C0862

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