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Entry
CA00021                                                            

Classification
Carotenoid Name
Staphyloxanthin;
4'-(D-Glucopyranoxyloxy)-4,4'-diaponeurosporen-4-oic acid ester
IUPAC name 4,4'-Diapo-4-[(6-O-12-methyltetradecanoyloxy-beta-D-Glucopyranosyl)oxy]-7',8'-dihydro-psi,psi-carotene-4-oic acid
Formula
C51H78O8
Molecular Weight 
819.134 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Orange color (Ref.508).
  • Number of
    conjugated double bonds 
    10 including one ketone (10 in total)
    Number of
    conjugated multiple bonds 
    10 including one ketone (10 in total)
    Isomers 
  • Constitutional isomer: CA00024
  • InChI
    InChI=1S/C51H78O8/c1-10-39(4)26-17-15-13-11-12-14-16-18-36-46(52)57-37-45-47(53)48(54)49(55)51(58-45)59-50(56)44(9)35-24-34-43(8)33-23-31-41(6)28-20-19-27-40(5)30-22-32-42(7)29-21-25-38(2)3/h19-20,22-25,27-28,30-35,39,45,47-49,51,53-55H,10-18,21,26,29,36-37H2,1-9H3/b20-19+,30-22+,31-23+,34-24+,40-27+,41-28+,42-32+,43-33+,44-35+/t39?,45-,47-,48+,49-,51+/m1/s1
    InChIKey
    PDOUICUKTQRPHO-MENSNCDRSA-N
    Canonical SMILES
    CCC(CCCCCCCCCCC(=O)OC[C@H]1O[C@@H](OC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C)/C)/C)/C)[C@@H]([C@H]([C@@H]1O)O)O)C
    XLogP
    15.554
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    8
    LipinskiFailures
    2
    Complexity of molecule
    0.044
    Number of heavy atoms
    59
    TPSA
    (Topological Polar Surface Area) 
    122.520 Å2
    Source organisms
    Staphylococcus aureus 209P (Ref.133) - Firmicutes - Bacilli
    References
  • Ref.133 : Richard, F. Taylor, Microbiological Reviews, Spet. 1984, pp. 181-198, "Bacterial Triterpenoids".
  • Ref.508 : Wieland B, Feil C, Gloria-Maercker E, Thumm G, Lechner M, Bravo JM, Poralla K, Götz F., J Bacteriol. 1994 Dec;176(24):7719-26., PMID: 8002598, "Genetic and biochemical analyses of the biosynthesis of the yellow carotenoid 4,4'-diaponeurosporene of Staphylococcus aureus.".
  • CAS
    71869-01-7
    Links to other DB
    KEGG COMPOUND: C16148
    ProCarDB: C1641

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