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Entry
CA00915                                                            

Classification
Carotenoid Name
Decaprenoxanthin monoglucoside
IUPAC name (2R,6R,2'R,6'R)-2-[4-(beta-D-Glucopyranosyloxy)-3-methylbut-2-enyl]-2'-(4-hydroxy-3-methylbut-2-enyl)-epsilon,epsilon-carotene
Formula
C57H84O7
Molecular Weight 
881.242 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI
InChI=1S/C57H84O7/c1-38(18-14-15-19-39(2)21-17-23-41(4)26-33-50-44(7)28-31-48(57(50,12)13)34-45(8)46(9)35-58)20-16-22-40(3)25-32-49-43(6)27-30-47(56(49,10)11)29-24-42(5)37-63-55-54(62)53(61)52(60)51(36-59)64-55/h14-28,32-33,47-55,58-62H,29-31,34-37H2,1-13H3/b15-14+,20-16+,21-17+,32-25+,33-26+,38-18+,39-19+,40-22+,41-23+,42-24+,46-45+/t47-,48+,49+,50+,51+,52+,53-,54+,55+/m0/s1
InChIKey
XTGXOIOSCAYUME-PIJQLACMSA-N
Canonical SMILES
OC[C@H]1O[C@@H](OC/C(=C/C[C@H]2CC=C([C@H](C2(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]2C(=CC[C@@H](C2(C)C)C/C(=C(/CO)\C)/C)C)\C)\C)/C)/C)C)/C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
14.564
Hydrogen Bond donors
(Lipinski's definition)
5
Hydrogen Bond Acceptors
(Lipinski's definition)
7
LipinskiFailures
2
Complexity of molecule
0.277
Number of heavy atoms
64
TPSA
(Topological Polar Surface Area) 
119.610 Å2
Source organisms
Arthrobacter sp. (Ref.334) - Actinobacteria
Corynebacterium glutamicum (Ref.242) - Actinobacteria: amino acid producing bacteria
References
  • Ref.334 : Arpin, N.; Liaaen-Jensen, S.; Trouilloud, M., Acta Chemica Scandinavica, 26(1972), Pages: 2524-2526, "Bacterial Carotenoids. XXXVIII. C50-Carotenoids. 9. Isolation of Decaprenoxanthin Mono- and Diglucoside from an Arthrobacter sp.".
  • Ref.242 : Krubasik, Philipp; Takaichi, Shinichi; Maoka, Takashi; Kobayashi, Miki; Masamoto, Kazumori; Sandmann, Gerhard, Archives of Microbiology¬†(2001),¬†176(3),¬†217-223., "Detailed biosynthetic pathway to decaprenoxanthin diglucoside in Corynebacterium glutamicum and identification of novel intermediates".
  • CAS
    30508-50-0
    Links to other DB
    KNApSAcK: C00023092

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