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Entry
CA00901                                                            
Classification
Carotenoid Name
Crocin 3;
Crocetin monogentiobiosyl ester;
Crocin C
IUPAC name 8-beta-Gentiobiosyl-8'-hydrogen 8,8'-diapocarotene-8,8'-dioate
Formula
C32H44O14
Molecular Weight 
652.672 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Strong tyrosinase inhibitory activity (Ref.485).
    • Number of
    conjugated double bonds 
    9 including one carboxylic acid and one carboxylic acid glucosyl ester (9 in total)
    Number of
    conjugated multiple bonds 
    9 including two carboxylic acid glucosylates (9 in total)
    Isomers 
  • Constitutional isomer: CA00902
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    1.629
    Hydrogen Bond donors
    (Lipinski's definition)
    8
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    14
    LipinskiFailures
    3
    Complexity of molecule
    0.156
    Number of heavy atoms
    46
    TPSA
    (Topological Polar Surface Area) 
    232.900 Å2
    Reaction
  • Substrate: CR00311
  • Product: CR00308
    • Pathway
  • Pathway: CB000082,  CB000083
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Gardenia Jasminoides (Ref.159, Ref.383) - Land plant: gardenia (Streptophyta - Rubiaceae)
    References
  • Ref.159: Coran, Silvia A.; Mulas, Stefano; Vasconi, Alessio, Journal of Chromatography A (2014), 1325, 221-226., "Profiling of components and validated determination of iridoids in Gardenia Jasminoides Ellis fruit by a high-​ performance-t​ hin-l​ ayer- chromatography/​ mass spectrometry approach".
  • Ref.383: Mai Nagatoshia, Kazuyoshi Terasakaa, Miki Owakia, Makiko Sotaa, Tatsunori Inukaia, Akito Nagatsub, Hajime Mizukami, FEBS letters, Volume 586, Issue 7, 5 April 2012, Pages 1055–1061, "UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin in Gardenia jasminoides".
  • Ref.485: Li CY, Wu TS, Journal of Natural Products [2002, 65(10):1452-1456], DOI: 10.1021/np020188v, "Constituents of the stigmas of Crocus sativus and their tyrosinase inhibitory activity.".
    • CAS
    55750-85-1
    Links to other DB

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