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Entry
CA00285                                                            

Classification
Carotenoid Name
Citranaxanthin
IUPAC name 5',6'-Dihydro-5'-apo-18'-nor-beta,psi-caroten-6'-one
Formula
C33H44O
Molecular Weight 
456.682 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including one ketone (11 in total)
Number of
conjugated multiple bonds 
11 including one ketone (11 in total)
Isomers 
InChI
InChI=1S/C33H44O/c1-26(16-11-18-28(3)21-23-31(6)34)14-9-10-15-27(2)17-12-19-29(4)22-24-32-30(5)20-13-25-33(32,7)8/h9-12,14-19,21-24H,13,20,25H2,1-8H3/b10-9+,16-11+,17-12+,23-21+,24-22+,26-14+,27-15+,28-18+,29-19+
InChIKey
PRDJTOVRIHGKNU-ZWERVMMHSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C(=O)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
XLogP
10.770
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.077
Number of heavy atoms
34
TPSA
(Topological Polar Surface Area) 
17.070 Å2
Source organisms
Sinton citrangequat (Ref.267) - Land plant: citrus hybrid of a citrange and a kumquat
Gallus gallus (Ref.219) - Bird: chicken
References
  • Ref.267 : Henry Yokoyama , Michael J. White, J. Org. Chem., 1965, 30 (7), pp 2481–2482 DOI: 10.1021/jo01018a521, "Citrus Carotenoids. II. The Structure of Citranaxanthin, a New Carotenoid Ketone".
  • Ref.219 : Brulc, Lucka; Simonovska, Breda; Vovk, Irena; Glavnik, Vesna, Journal of Chromatography A (2013), 1318, 134-141. "Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography".
  • CAS
    3604-90-8
    Links to other DB
    KNApSAcK: C00023104

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