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Entry
CA00838                                                            

Classification
Carotenoid Name
Paracentrone
IUPAC name (3S,5R,6R)-3,5-Dihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-7'-apo-beta-caroten-8'-one
Formula
C31H42O3
Molecular Weight 
462.646 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one (9 in total)
Number of
conjugated multiple bonds 
9 including one (9 in total)
Isomers 
  • Constitutional isomer: CA01008, CA00792, CA00860
  • InChI
    InChI=1S/C31H42O3/c1-23(13-9-10-14-24(2)17-12-18-26(4)27(5)32)15-11-16-25(3)19-20-29-30(6,7)21-28(33)22-31(29,8)34/h9-19,28,33-34H,21-22H2,1-8H3/b10-9+,15-11+,17-12+,23-13+,24-14+,25-16+,26-18+/t20-,28-,31+/m0/s1
    InChIKey
    DBFXUHLRCRLMIU-FMTKEWENSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)\C
    XLogP
    8.335
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.079
    Number of heavy atoms
    34
    TPSA
    (Topological Polar Surface Area) 
    57.530 Å2
    Source organisms
    Solorina crocea (Ref.374) - Fungi: lichen
    Echinoidea sp. (Ref.375) - Sea urchin
    References
  • Ref.374 : Czeczuga, Bazyli; Olech, Maria, Phyton (Horn, Austria) (1990), 30(2), 235-45., "Investigations on carotenoids in lichens.  XXV.  Studies of carotenoids in lichens from Spitsbergen".
  • Ref.375 : Galasko, Gail; Hora, J.; Toube, T. P.; Weedon, B. C. L.; Andre, D.; Barbier, M.; Lederer, E.; Villanueva, V. R., Journal of the Chemical Society [Section] C:  Organic (1969), (9), 1264-5., "Carotenoids and related compounds.  XXII.  Allenic carotenoids in sea urchins".
  • CAS
    31190-20-2
    Links to other DB
    KNApSAcK: C00023110

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