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Entry
CA00903                                                            

Classification
Carotenoid Name
Crocin 2;
Crocin B;
Tricrocin;
Crocetin gentiobiosyl glucosyl ester
IUPAC name 8-beta-Gentiobiosyl-8'-beta-D-glucosy-8,8'-diapocarotene-8,8'-dioate
Formula
C38H54O19
Molecular Weight 
814.812 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including two carboxylic acid glucosylates (9 in total)
Number of
conjugated multiple bonds 
9 including two carboxylic acid glucosylates (9 in total)
Isomers 
InChI
InChI=1S/C38H54O19/c1-18(11-7-13-20(3)34(50)56-37-32(48)29(45)26(42)23(16-40)54-37)9-5-6-10-19(2)12-8-14-21(4)35(51)57-38-33(49)30(46)27(43)24(55-38)17-52-36-31(47)28(44)25(41)22(15-39)53-36/h5-14,22-33,36-49H,15-17H2,1-4H3/b6-5+,11-7+,12-8+,18-9+,19-10+,20-13+,21-14+/t22-,23-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,36-,37+,38+/m1/s1
InChIKey
CZSBHMFVVLYIQQ-DRVLGOCHSA-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@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)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
0.323
Hydrogen Bond donors
(Lipinski's definition)
11
Hydrogen Bond Acceptors
(Lipinski's definition)
19
LipinskiFailures
3
Complexity of molecule
0.342
Number of heavy atoms
57
TPSA
(Topological Polar Surface Area) 
312.050 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".
  • CAS
    55750-84-0
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