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Entry
CA00011                                                            

Classification
Carotenoid Name
4,4'-Diaponeurosporen-4-al;
4,4'-Diaponeurosporen-4'-al;
Diaponeurosporenal
IUPAC name 7',8'-Dihydro-4,4'-diapo-psi,psi-caroten-4-al
Formula
C30H40O
Molecular Weight 
416.62 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10
Number of
conjugated multiple bonds 
10
Isomers 
  • Constitutional isomer: CA00789, CA00825
  • InChI
    InChI=1S/C30H40O/c1-25(2)14-10-17-28(5)20-11-18-26(3)15-8-9-16-27(4)19-12-21-29(6)22-13-23-30(7)24-31/h8-9,11-16,18-24H,10,17H2,1-7H3/b9-8+,18-11+,19-12+,22-13+,26-15+,27-16+,28-20+,29-21+,30-23+
    InChIKey
    XDVAYNOICRRSLG-ZVLLIQJTSA-N
    Canonical SMILES
    O=C/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
    XLogP
    9.610
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    31
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Streptococcus faecium UNH 564P (Ref.70, Ref.71, Ref.540) - Firmicutes - Bacilli
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Staphylococcus aureus (Ref.75) - Firmicutes - Bacilli
    References
  • Ref.70 : Davies, Brian H.; Taylor, Richard F., Canadian Journal of Biochemistry (1982), 60(6), 684-92., "The biosynthesis of triterpenoid carotenoids in Streptococcus faecium UNH 564P".
  • Ref.71 : Taylor, Richard F.; Davies, Brian H., Biochemical Journal (1976), 153(2), 233-9., "Triterpenoid carotenoids and related lipids. Triterpenoid carotenoid aldehydes from Streptococcus faecium UNH 564P".
  • Ref.540 : Benjamin N. Mijts, Pyung Cheon Lee, Claudia Schmidt-Dannert, Chemistry & Biology, Volume 12, Issue 4, April 2005, Pages 453–460, "Identification of a Carotenoid Oxygenase Synthesizing Acyclic Xanthophylls: Combinatorial Biosynthesis and Directed Evolution".
  • Ref.72 : Heo, Jinsol; Kim, Se Hyeuk; Lee, Pyung Cheon, Applied and Environmental Microbiology (2013), 79(11), 3336-3345., "New insight into the cleavage reaction of Nostoc sp. strain PCC 7120 carotenoid cleavage dioxygenase in natural and nonnatural carotenoids".
  • 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".
  • CAS
    59057-70-4
    Links to other DB
    KNApSAcK: C00023141
    LipidBank: VCA1192
    ProCarDB: C1842

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