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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00006,  CR00137,  CR00223
  • Product: CR00133,  CR00273
    • Pathway
  • Pathway: CB000001,  CB000002,  CB000003
    • Major carotenoid information
    Dominant pigment in heliobacteria (Heliobacillus mobilis, Heliophilum fasciatum, Heliobacterium chlorum, Heliobacterium modesticaldum, and Heliobacterium gestii) (Ref.188). The major pigment produced by Staphylococcus aureus Newman (Ref.727)
    Minor carotenoid information

    Source organisms
    Staphylococcus aureus (Ref.508, Ref.540) - Firmicutes - Bacilli (Firmicutes - Staphylococcaceae)
    Lactobacillus plantarum (Ref.74) - Firmicutes - Bacilli (Firmicutes - Lactobacillaceae)
    Heliobacillus mobilis (Ref.188) - Firmicutes - Clostridia (Firmicutes - Heliobacteriaceae)
    Heliophilum fasciatum (Ref.188) - Firmicutes - Clostridia (Firmicutes - Heliobacteriaceae)
    Heliobacterium chlorum (Ref.188) - Firmicutes - Clostridia (Firmicutes - Heliobacteriaceae)
    Heliobacterium modesticaldum (Ref.188) - Firmicutes - Clostridia (Firmicutes - Heliobacteriaceae)
    Heliobacterium gestii (Ref.188) - Firmicutes - Clostridia (Firmicutes - Heliobacteriaceae)
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120 (Cyanobacteria - Nostocaceae)
    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".
  • Ref.727: B. Wieland et al., JOURNAL OF BACrERIOLOGY, Dec. 1994, p. 7719-7726, "Genetic and Biochemical Analyses of the Biosynthesis of the Yellow Carotenoid 4,4'-Diaponeurosporene of Staphylococcus aureus".
    • CAS
    53872-50-7
    Links to other DB
    KEGG COMPOUND: C16145
    KNApSAcK: C00023134
    LipidBank: VCA1050
    ProCarDB: C1838

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