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Entry
CA00775                                                            
Classification
Carotenoid Name
Isorenieratene-3,3'-diol;
3,3'-Dihydroxyisorenieratene
IUPAC name phi,phi-Caroten-3,3-diol
Formula
C40H48O2
Molecular Weight 
560.784 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Superior properties in preventing photo- and photooxidative damages (Ref.771).
    • Number of
    conjugated double bonds 
    15
    Number of
    conjugated multiple bonds 
    15
    Isomers 
  • Constitutional isomer: CA01125, CA00463, CA00725, CA00732
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    13.246
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.333
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    40.460 Å2
    Reaction
    Pathway
    Major carotenoid information
    Major carotnoid in Streptomyces argillaceus (Ref.771).
    Minor carotenoid information

    Source organisms
    Mycobacterium tuberculosis (Ref.83) - Actinobacteria (Actinobacteria - Mycobacteriaceae)
    Brevibacterium aurantiacum sp. nov. (Ref.84) - Actinobacteria (Actinobacteria - Brevibacteriaceae)
    Brevibacterium linens (Ref.85) - Actinobacteria (Actinobacteria - Brevibacteriaceae)
    Streptomyces argillaceus (Ref.771) - Actinobacteria (Actinobacteria - Streptomycetaceae)
    Streptomyces mediolani (Ref.86, Ref.87) - Actinobacteria (Actinobacteria - Streptomycetaceae)
    References
  • Ref.83: Scherzinger, Daniel; Scheffer, Erdmann; Baer, Cornelia; Ernst, Hansgeorg; Al-Babili, Salim, FEBS Journal (2010), 277(22), 4662-4673., "The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids".
  • Ref.84: Dufosse, L.; de Echanove, M. C., Food Research International (2005), 38(8-9), 967-973., " The last step in the biosynthesis of aryl carotenoids in the cheese ripening bacteria Brevibacterium linens ATCC 9175 (Brevibacterium aurantiacum sp. nov.) involves a cytochrome P450-​dependent monooxygenase".
  • Ref.85: Kohl, Werner; Achenbach, Hans; Reichenbach, Hans, Phytochemistry (Elsevier) (1983), 22(1), 207-10., "Investigations on metabolites of microorganisms. Part 24. The pigments of Brevibacterium linens: aromatic carotenoids".
  • Ref.86: Arcamone, Federico; Camerion, Bruno; Franceschi, Giovanni; Penco, Sergio, Gazzetta Chimica Italiana (1970), 100(6), 581-90., "Structure and synthesis of new phenolic carotenoids from Streptomyces mediolani".
  • Ref.87: Arcamone, Federico; Camerino, Bruno; Cotta, E.; Franceschi, Giovanni; Grein, Arpad; Penco, Sergio; Spalla, Celestino, Experientia (1969), 25(3), 241-2., "Carotenoids from Streptomyces mediolani".
  • Ref.771: Adriana Becerril et al., PLOS ONE | https://doi.org/10.1371/journal.pone.0198145 May 24, 2018, “Uncovering production of specialized metabolites by Streptomyces argillaceus: Activation of cryptic biosynthesis gene clusters using nutritional and genetic approaches”.
    • CAS
    23394-41-4
    Links to other DB
    KNApSAcK: C00022888

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