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Entry
CA00475                                                            

Classification
Carotenoid Name
3'-Hydroxyechinenone;
(3'R)-3'-Hydroxyechinenone;
Asteroidenone
IUPAC name (3'R)-3'-Hydroxy-beta,beta-caroten-4-one
Formula
C40H54O2
Molecular Weight 
566.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
12 including one ketone (12 in total)
Number of
conjugated multiple bonds 
12 including one ketone (12 in total)
Isomers 
InChI

InChIKey

Canonical SMILES

XLogP
10.676
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.312
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
37.300 Å2
Reaction
  • Substrate: CR00184,  CR00256
  • Product: CR00186,  CR00255
  • Pathway
  • Pathway: CB000057,  CB000062
  • Major carotenoid information
    Major carotenoid in Synechocystis sp. PCC 6803 (Ref.732).
    Minor carotenoid information

    Source organisms
    Arthrospira sp. (Ref.3) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Oscillantoria rubescens (Ref.3) - Cyanobacteria: other name is Planktothrix rubescens (Cyanobacteria - Microcoleaceae)
    Spirulina maxima (Ref.3) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Microcystis aeruginosa (Ref.3) - Cyanobacteria (Cyanobacteria - Microcystaceae)
    Aphanizomenon flos-aquae (Ref.3) - Cyanobacteria (Cyanobacteria - Aphanizomenonaceae)
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    References
  • Ref.3: T. K. Holt and D. W. Krogmann, Biochimica et Biophysica Acta, 637 (1981) 408-414 "A carotenoid-protein from cyanobacteria".
  • Ref.19: Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • Ref.732: S. Takaichia and M. Mochimaru, Cell. Mol. Life Sci. 64 (2007) 2607 – 2619, "Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides", DOI 10.1007/s00018-007-7190-z.
  • CAS
    4481-36-1
    Links to other DB
    KEGG COMPOUND: C15965
    KNApSAcK: C00022980
    LipidBank: VCA1016
    MassBank: CA000145

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