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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 
    InChI
    InChI=1S/C32H44O14/c1-17(11-7-13-19(3)29(40)41)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(39)26(37)24(35)22(45-32)16-43-31-27(38)25(36)23(34)21(15-33)44-31/h5-14,21-28,31-39H,15-16H2,1-4H3,(H,40,41)/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+/t21-,22-,23-,24-,25+,26+,27-,28-,31-,32+/m1/s1
    InChIKey
    VULLCGFNYWDRHL-YJOFKXFJSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)O)\C)\C)/C)/C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
    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
    Source organisms
    Gardenia Jasminoides (Ref.159, Ref.383) - Land plant: gardenia
    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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