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Entry
CA00164                                                            

Classification
Carotenoid Name
Demethylspheroidenone;
Desmethylspheroidenone
IUPAC name 1-Hydroxy-3,4-didehydro-1,2,7',8'-tetrahydro-psi,psi-caroten-2-one
Formula
C40H56O2
Molecular Weight 
568.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including one ketone (11 in total)
Number of
conjugated multiple bonds 
11 including one ketone (11 in total)
Isomers 
InChI
InChI=1S/C40H56O2/c1-32(2)18-13-21-35(5)24-16-27-36(6)25-14-22-33(3)19-11-12-20-34(4)23-15-26-37(7)28-17-29-38(8)30-31-39(41)40(9,10)42/h11-12,14-15,17-20,22-26,28-31,42H,13,16,21,27H2,1-10H3/b12-11+,22-14+,23-15+,28-17+,31-30+,33-19+,34-20+,35-24+,36-25+,37-26+,38-29+
InChIKey
YXTRGWPAUSOLAD-HMSUWCNJSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\C=C\C(=O)C(O)(C)C)/C)/C)/C)/C=C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C
XLogP
12.117
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.000
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
37.300 Å2
Source organisms
Rhodobaca bogoriensis (Ref.339) - Alphaproteobacteria: alkaliphilic purple non-sulfur bacteria from African Rift Valley soda lakes
Rhodopseudomonas capsulata (Ref.340) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
References
  • Ref.339 : Takaichi, Shinichi; Jung, Deborah O.; Madigan, Michael T., Photosynthesis Research (2001), 67(3), 207-214., "Accumulation of unusual carotenoids in the spheroidene pathway, demethylspheroidene and demethylspheroidenone, in an alkaliphilic purple nonsulfur bacterium Rhodobaca bogoriensis".
  • Ref.340 : Manwaring, Jacqueline; Evans, E. Hilary; Britton, George; Schneider, Dieter R., FEBS Letters (1980), 110(1), 47-9., "The identification of demethylspheroidenone as a major carotenoid in aerobic cultures of Rhodopseudomonas capsulata".
  • CAS
    70303-34-3
    Links to other DB
    KNApSAcK: C00000924
    LipidBank: VCA1070

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