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Entry
CA00022                                                            

Classification
Carotenoid Name
β-D-glucosyl 4,4'-diaponeurosporenoic acid;
beta-D-glucosyl 4,4'-diaponeurosporenoic acid;
Glycosyl-4,4'-diaponeurosporenoate
IUPAC name 4,4'-Diapo-4-(beta-D-Glucopyranosyloxy)-7',8'-dihydro-psi,psi-carotene-4-oic acid-ester
Formula
C36H50O7
Molecular Weight 
594.76 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10 including one ketone (10 intotal)
Number of
conjugated multiple bonds 
10 including one ketone (10 intotal)
Isomers 
InChI
InChI=1S/C36H50O7/c1-25(2)14-10-17-28(5)20-11-18-26(3)15-8-9-16-27(4)19-12-21-29(6)22-13-23-30(7)35(41)43-36-34(40)33(39)32(38)31(24-37)42-36/h8-9,11-16,18-23,31-34,36-40H,10,17,24H2,1-7H3/b9-8+,18-11+,19-12+,22-13+,26-15+,27-16+,28-20+,29-21+,30-23+/t31-,32-,33+,34-,36+/m1/s1
InChIKey
ZBQZCMIYCTXPBB-GQBMLQGDSA-N
Canonical SMILES
OC[C@H]1O[C@@H](OC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C)/C)/C)/C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
8.223
Hydrogen Bond donors
(Lipinski's definition)
4
Hydrogen Bond Acceptors
(Lipinski's definition)
7
LipinskiFailures
2
Complexity of molecule
0.065
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
116.450 Å2
Source organisms
Staphylococcus aureus (Ref.192, Ref.75, Ref.540) - Firmicutes - Bacilli
References
  • Ref.192 : Pelz, Alexandra; Wieland, Karsten-Peter; Putzbach, Karsten; Hentschel, Petra; Albert, Klaus; Goetz, Friedrich, Journal of Biological Chemistry (2005), 280(37), 32493-32498., "Structure and Biosynthesis of Staphyloxanthin from Staphylococcus aureus".
  • Ref.75 : Marshall, John H.; Wilmoth, Gregory H., Journal of Bacteriology (1981), 147(3), 900-13., "Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids".
  • Ref.540 : Benjamin N. Mijts, Pyung Cheon Lee, Claudia Schmidt-Dannert, Chemistry & Biology, Volume 12, Issue 4, April 2005, Pages 453–460, "Identification of a Carotenoid Oxygenase Synthesizing Acyclic Xanthophylls: Combinatorial Biosynthesis and Directed Evolution".
  • CAS
    -
    Links to other DB
    KEGG COMPOUND: C16147
    ProCarDB: C1648

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