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Entry
CA00171                                                            

Classification
Carotenoid Name
Hydroxyspheroidenone;
Spheroidenonol;
1',2'-dihydro-1'-hydroxy-spheroidenone
IUPAC name 1'-Hydroxy-1-methoxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-psi,psi-caroten-2-one
Formula
C41H60O3
Molecular Weight 
600.89 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 
  • Constitutional isomer: CA00172
  • InChI
    InChI=1S/C41H60O3/c1-33(21-14-23-35(3)25-16-27-37(5)29-18-32-40(7,8)43)19-12-13-20-34(2)22-15-24-36(4)26-17-28-38(6)30-31-39(42)41(9,10)44-11/h12-15,17,19-24,26-28,30-31,43H,16,18,25,29,32H2,1-11H3/b13-12+,21-14+,22-15+,26-17+,31-30+,33-19+,34-20+,35-23+,36-24+,37-27+,38-28+
    InChIKey
    RUIGAJAIJJUKFM-PZWPVEARSA-N
    Canonical SMILES
    COC(C(=O)/C=C/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/CC/C=C(/CCCC(O)(C)C)\C)\C)\C)/C)/C)/C)(C)C
    XLogP
    11.528
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    46.530 Å2
    Source organisms
    Rhodopseudomonas spheroides (Ref.342) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodopseudomonas gelatinosa (Ref.342) - Betaproteobacteria: purple nonsulfur bacteria
    Rubrivivax gelatinosus (Ref.354) - Betaproteobacteria: phototrophic purple nonsulfur bacteria
    Rhodopesudomonnas palustris (Ref.344) - 
    References
  • Ref.342 : Jackman, L. M.; Jensen, S. Liaaen, Acta Chemica Scandinavica (1403-1411)(1964), Pages: 1403-1411, "Bacterial Carotenoids. XV. On the Constitution of the Minor Carotenoids of Rhodopseudomonas. 5. The Structures of P518 (2,2'-Diketo-spirilloxanthin), OH-R (OH-Spheroidenone), and OH-Y (OH-Spheroidene).".
  • Ref.354 : Jirsakova, Vladimira; Reiss-Husson, Francoise; van Dijk, Bas; Owen, Gabrielle; Hoff, Arnold J., Photochemistry and Photobiology (1996), 64(2), 363-368., "Characterization of carotenoid triplet states in the light-harvesting complex B800-850 from the purple bacterium Rubrivivax gelatinosus".
  • Ref.344 : Zhao, Chun-gui; Fu, Qiao-ming; Zhuo, Min-quan; Yang, Su-ping, Weishengwuxue Tongbao (2014), 41(7), 1448-1455., "The relative polarity and stability of each carotenoid of spirilloxanthin biosynthesis pathway by thin-layer chromatography (TLC)".
  • CAS
    1119-39-7
    Links to other DB
    KEGG COMPOUND: C15905
    LipidBank: VCA1069
    ProCarDB: C1885

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