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Entry
CA00179                                                            

Classification
Carotenoid Name
2,2'-Diketospirilloxanthin;
2,2'-dioxospirilloxanthin;
Rhodoviolascin-2,2'-dione;
P 518
IUPAC name 1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-carotene-2,2'-dione
Formula
C42H56O4
Molecular Weight 
624.868 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
15 including two ketones (15 in total)
Number of
conjugated multiple bonds 
15 including two ketones (15 in total)
Isomers 
  • Constitutional isomer: CA00515
  • InChI
    InChI=1S/C42H56O4/c1-33(21-15-23-35(3)25-17-27-37(5)29-31-39(43)41(7,8)45-11)19-13-14-20-34(2)22-16-24-36(4)26-18-28-38(6)30-32-40(44)42(9,10)46-12/h13-32H,1-12H3/b14-13+,21-15+,22-16+,25-17+,26-18+,31-29+,32-30+,33-19+,34-20+,35-23+,36-24+,37-27+,38-28+
    InChIKey
    MNKGOUOMGDXWPK-YDDLGYPNSA-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(/C=C/C=C(/C=C/C(=O)C(OC)(C)C)\C)\C)\C)/C)/C)/C)(C)C
    XLogP
    10.602
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    46
    TPSA
    (Topological Polar Surface Area) 
    52.600 Å2
    Source organisms
    Rhodobacter sphaeroides (Ref.343) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    References
  • Ref.343 : Niedzwiedzki, Dariusz M.; Dilbeck, Preston L.; Tang, Qun; Mothersole, David J.; Martin, Elizabeth C.; Bocian, David F.; Holten, Dewey; Hunter, C. Neil, Niedzwiedzki, Dariusz M.; Dilbeck, Preston L.; Tang, Qun; Mothersole, David J.; Martin, Elizabeth C.; Bocian, David F.; Holten, Dewey; Hunter, C. Neil, "Functional characteristics of spirilloxanthin and keto-bearing Analogues in light-harvesting LH2 complexes from Rhodobacter sphaeroides with a genetically modified carotenoid synthesis pathway".
  • CAS
    1185-31-5, 24009-17-4
    Links to other DB
    KEGG COMPOUND: C15885
    KNApSAcK: C00023064
    LipidBank: VCA1072
    ProCarDB: C0401

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