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Entry
CA00015                                                            

Classification
Carotenoid Name
4,4'-Diaponeurosporen-4-oic acid
IUPAC name 7',8'-Dihydro-4,4'-diapo-psi,psi-caroten-4-oic acid
Formula
C30H40O2
Molecular Weight 
432.62 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: CA01126, CA00880, CA00853, CA00832
  • InChI
    InChI=1S/C30H40O2/c1-24(2)14-10-17-27(5)20-11-18-25(3)15-8-9-16-26(4)19-12-21-28(6)22-13-23-29(7)30(31)32/h8-9,11-16,18-23H,10,17H2,1-7H3,(H,31,32)/b9-8+,18-11+,19-12+,22-13+,25-15+,26-16+,27-20+,28-21+,29-23+
    InChIKey
    NXJSQJIGCCIMAE-ORIYTCASSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\CCC=C(C)C)/C)/C)/C=C/C=C(/C=C/C=C(/C(=O)O)\C)\C
    XLogP
    9.529
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    32
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Staphylococcus aureus (Ref.75, Ref.540) - Firmicutes - Bacilli
    References
  • 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".
  • 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".
  • CAS
    79679-53-1
    Links to other DB
    KEGG COMPOUND: C16146
    KNApSAcK: C00023144
    LipidBank: VCA1193
    ProCarDB: C1647

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