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Entry
CA00018                                                            

Classification
Carotenoid Name
Diapolycopenedioic acid glucosyl ester
IUPAC name 4-beta-D-Glucopyranosyl hydrogen 4,4'-diapo-psi,psi-carotene-4,4'-dioate
Formula
C36H46O9
Molecular Weight 
622.728 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including two ketones (13 in total)
Number of
conjugated multiple bonds 
13 including two ketones (13 in total)
Isomers 
InChI
InChI=1S/C36H46O9/c1-24(15-9-17-26(3)19-11-21-28(5)34(41)42)13-7-8-14-25(2)16-10-18-27(4)20-12-22-29(6)35(43)45-36-33(40)32(39)31(38)30(23-37)44-36/h7-22,30-33,36-40H,23H2,1-6H3,(H,41,42)/b8-7+,15-9+,16-10+,19-11+,20-12+,24-13+,25-14+,26-17+,27-18+,28-21+,29-22+/t30-,31-,32+,33-,36+/m1/s1
InChIKey
XAPKOWJMHPKSFE-QMDZEWDVSA-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(/C=C/C=C(/C(=O)O)\C)\C)\C)/C)/C)/C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
6.726
Hydrogen Bond donors
(Lipinski's definition)
5
Hydrogen Bond Acceptors
(Lipinski's definition)
9
LipinskiFailures
2
Complexity of molecule
0.066
Number of heavy atoms
45
TPSA
(Topological Polar Surface Area) 
153.750 Å2
Source organisms
Rhizobium sp. (Ref.82) - Alphaproteobacteria: root nodule bacterium
Methylobacterium rhodinum -formerly Pseudomonas rhodos (Ref.73) - Alphaproteobacteria
References
  • Ref.82 : Kleinig, H.; Broughton, W. J., Archives of Microbiology (1982), 133(2), 164., "Carotenoid pigments in a red strain of Rhizobium from Lotononis bainesii Baker".
  • Ref.73 : Kleinig, Hans; Schmitt, Ruediger; Meister, Walter; Englert, Gerhard; Thommen, Hans, Zeitschrift fuer Naturforschung, C: Journal of Biosciences (1979), 34C(3-4), 181-5., "New C30-​carotenoic acid glucosyl esters from Pseudomonas rhodos".
  • CAS
    70240-67-4
    Links to other DB
    KNApSAcK: C00023145

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