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Entry
CA00105                                                            

Classification
Carotenoid Name
Dihydroxylycopene diglucoside
IUPAC name 1,1'-Di-(beta-D-glucopyranosyloxy)-1,2,1',2'-tetrahydro-psi,psi-carotene
Formula
C52H80O12
Molecular Weight 
897.16 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C52H80O12/c1-35(21-13-23-37(3)25-15-27-39(5)29-17-31-51(7,8)63-49-47(59)45(57)43(55)41(33-53)61-49)19-11-12-20-36(2)22-14-24-38(4)26-16-28-40(6)30-18-32-52(9,10)64-50-48(60)46(58)44(56)42(34-54)62-50/h11-16,19-28,41-50,53-60H,17-18,29-34H2,1-10H3/b12-11+,21-13+,22-14+,25-15+,26-16+,35-19+,36-20+,37-23+,38-24+,39-27+,40-28+/t41-,42-,43-,44-,45+,46+,47-,48-,49+,50+/m1/s1
InChIKey
ZJEXZWYLJSEOID-PYCHGLIGSA-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@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)(C)C)\C)\C)\C)/C)/C)/C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
10.154
Hydrogen Bond donors
(Lipinski's definition)
8
Hydrogen Bond Acceptors
(Lipinski's definition)
12
LipinskiFailures
4
Complexity of molecule
0.306
Number of heavy atoms
64
TPSA
(Topological Polar Surface Area) 
198.760 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
    345908-76-1
    Links to other DB
    KNApSAcK: C00022900
    ProCarDB: C0178

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