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Entry
CA00474                                                            

Classification
Carotenoid Name
(3R)-3-Hydroxyechinenone
IUPAC name (3R)-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(18-13-20-31(3)23-25-35-33(5)22-15-27-39(35,7)8)16-11-12-17-30(2)19-14-21-32(4)24-26-36-34(6)38(42)37(41)28-40(36,9)10/h11-14,16-21,23-26,37,41H,15,22,27-28H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,29-16+,30-17+,31-20+,32-21+/t37-/m0/s1
InChIKey
DFNMSBYEEKBETA-JZLJSYQFSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)[C@H](CC1(C)C)O)\C
XLogP
12.215
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
Euglena gracilis (Ref.37) - Alga: Euglenoid
Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglenoid
Protousnea sp. (Ref.388) - Fungi: lichen
References
  • Ref.37 : N. I. Krinsky, and T. H. Goldsmith, Archives of Biochemistry and Biophysics 91, 271-279 (1960), "The Carotenoids of the Flagellated Alga, Euglena gracilis".
  • Ref.41 : N. I. Krinsky, A. Gordon, and A. I. Stern, Plant Physiol 39: 441-445 1964, "The appearance of Neoxanthin during the Regreenin g of Dark-grown Euglena".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • CAS
    4339-77-9
    Links to other DB
    KEGG COMPOUND: C15966
    KNApSAcK: C00022977

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