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Entry
CA00002                                                            

Classification
Carotenoid Name
4,4'-Diaponeurosporene
IUPAC name 7,8-Dihydro-4,4'-diapo-psi,psi-carotene
Formula
C30H42
Molecular Weight 
402.636 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Deep-yellow color (Ref.508).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
  • Cis/trans isomer: CA00003, CA00004
  • InChI
    InChI=1S/C30H42/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h9-11,13-19,21-24H,12,20H2,1-8H3/b10-9+,19-11+,21-13+,22-14+,27-17+,28-18+,29-23+,30-24+
    InChIKey
    FPSYVUBUILNSRF-MQMKOTMBSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(C)C)/C)/C)/C=C/C=C(/CCC=C(C)C)\C
    XLogP
    10.984
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    30
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Lactobacillus plantarum (Ref.74) - Firmicutes - Bacilli
    Heliobacillus mobilis (Ref.188) - Firmicutes - Clostridia
    Heliophilum fasciatum (Ref.188) - Firmicutes - Clostridia
    Heliobacterium chlorum (Ref.188) - Firmicutes - Clostridia
    Heliobacterium modesticaldum (Ref.188) - Firmicutes - Clostridia
    Heliobacterium gestii (Ref.188) - Firmicutes - Clostridia
    Staphylococcus aureus (Ref.508, 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.74 : Juan Garrido-Fernández, Antonio Maldonado-Barragán, Belén Caballero-Guerrero, Dámaso Hornero-Méndez, José Luis Ruiz-Barba, International Journal of Food Microbiology, Volume 140, Issue 1, 30 May 2010, Pages 34–39, "Carotenoid production in Lactobacillus plantarum".
  • Ref.188 : Takaichi, S., K. Inoue, M. Akaike, M. Kobayashi, H. Ohoka, and M. T. Madigan. 1997. The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4,4-diaponeurosporene, not neurosporene. Arch. Microbiol. 168:277–281..
  • 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.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
    53872-50-7
    Links to other DB
    KEGG COMPOUND: C16145
    KNApSAcK: C00023134
    LipidBank: VCA1050
    ProCarDB: C1838

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