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Entry
CA00987                                                            

Classification
Carotenoid Name
Dihydroxylycopene glucoside;
Dihydroxylycopene monoglucoside
IUPAC name 1-(beta-D-glucopyranosyloxy)-1,2,1',2'-tetrahydro-psi,psi-carotene
Formula
C46H70O7
Molecular Weight 
735.02 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C46H70O7/c1-34(21-13-23-36(3)25-15-27-38(5)29-17-31-45(7,8)51)19-11-12-20-35(2)22-14-24-37(4)26-16-28-39(6)30-18-32-46(9,10)53-44-43(50)42(49)41(48)40(33-47)52-44/h11-16,19-28,40-44,47-51H,17-18,29-33H2,1-10H3/b12-11+,21-13+,22-14+,25-15+,26-16+,34-19+,35-20+,36-23+,37-24+,38-27+,39-28+/t40-,41-,42+,43-,44+/m1/s1
InChIKey
JRTHOMNAXRJSRF-XYDFVLFWSA-N
Canonical SMILES
OC[C@H]1O[C@@H](OC(CCC/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(/CCCC(O)(C)C)\C)\C)\C)/C)/C)/C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
11.262
Hydrogen Bond donors
(Lipinski's definition)
5
Hydrogen Bond Acceptors
(Lipinski's definition)
7
LipinskiFailures
2
Complexity of molecule
0.049
Number of heavy atoms
53
TPSA
(Topological Polar Surface Area) 
119.610 Å2
Source organisms
Halorhodospira abdelmalekii (Ref.326) - purple sulfur bacteria
Halorhodospira halochloris (Ref.326) - purple sulfur bacteria
Phaeospirillum sp. (Ref.327) - Alphaproteobacteria: spiral-shaped phototrophic purple non-sulfur bacteria
Roseospira sp. (Ref.327) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
References
  • Ref.326 : Shinichi Takaichi, Takashi Maoka, Satoshi Hanada, Johannes F. Imhoff, Archives of Microbiology, March 2001, Volume 175, Issue 3, pp 161-167, "Dihydroxylycopene diglucoside diesters: a novel class of carotenoids from the phototrophic purple sulfur bacteria Halorhodospira abdelmalekii and Halorhodospira halochloris".
  • Ref.327 : Takaichi, Shinichi; Maoka, Takashi; Sasikala, Ch.; Ramana, Ch. V.; Shimada, Keizo, Current Microbiology¬†(2011),¬†63(1),¬†75-80., "Genus specific unusual carotenoids in purple bacteria, Phaeospirillum and Roseospira: Structures and biosyntheses".
  • CAS
    345908-77-2
    Links to other DB
    ProCarDB: C0171

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