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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   
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
InChI=1S/C40H54O2/c1-29(17-13-19-31(3)21-23-36-33(5)27-35(41)28-40(36,9)10)15-11-12-16-30(2)18-14-20-32(4)22-24-37-34(6)38(42)25-26-39(37,7)8/h11-24,35,41H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-/m1/s1
InChIKey
ZRCXVNZZDQGBQT-BANQPSJHSA-N
Canonical SMILES
O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)C(=O)CCC1(C)C)\C)\C)/C)/C)C
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
Source organisms
Arthrospira sp. (Ref.3) - Cyanobacteria
Spirulina maxima (Ref.3) - Cyanobacteria
Aphanizomenon flos-aquae (Ref.3) - Cyanobacteria
Microcystis aeruginosa (Ref.3) - Cyanobacteria
Oscillantoria rubescens (Ref.3) - Cyanobacteria: other name is Planktothrix rubescens
Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
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".
  • CAS
    4481-36-1
    Links to other DB
    KEGG COMPOUND: C15965
    KNApSAcK: C00022980
    LipidBank: VCA1016
    MassBank: CA000145

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