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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Product: CR00289
    • Pathway
  • Pathway: CB000003
    • Major carotenoid information
    The main pigment of Staphylococcus aureus (Ref.726, Ref.192).
    Minor carotenoid information

    Source organisms
    Staphylococcus aureus 209P (Ref.133) - Firmicutes - Bacilli (Firmicutes - Staphylococcaceae)
    Staphylococcus aureus (Ref.75) - Firmicutes - Bacilli (Firmicutes - Staphylococcaceae)
    References
  • Ref.133: Richard, F. Taylor, Microbiological Reviews, Spet. 1984, pp. 181-198, "Bacterial Triterpenoids".
  • Ref.75: Marshall, John H.; Wilmoth, Gregory H., Journal of Bacteriology (1981), 147(3), 900-13., "Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids".
  • 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.".
  • Ref.726: Marshall JH, Wilmoth GJ., J Bacteriol. 1981 Sep;147(3):900-13., "Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids.", PMID: 7275936 PMCID: PMC216126.
  • Ref.192: Pelz, Alexandra; Wieland, Karsten-Peter; Putzbach, Karsten; Hentschel, Petra; Albert, Klaus; Goetz, Friedrich, Journal of Biological Chemistry (2005), 280(37), 32493-32498., "Structure and Biosynthesis of Staphyloxanthin from Staphylococcus aureus".
    • CAS
    71869-01-7
    Links to other DB
    KEGG COMPOUND: C16148
    ProCarDB: C1641

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