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Entry
CA00410                                                            
Classification
Carotenoid Name
Mutatoxanthin;
Citroxanthin;
Zeaxanthin furanoside
IUPAC name (3S,5R,8RS,3'R)-5,8-Epoxy-5,8-dihydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O3
Molecular Weight 
584.848 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/C40H56O3/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)25-38(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36-24-37-39(8,9)26-34(42)27-40(37,10)43-36/h11-22,24,33-34,36,41-42H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t33-,34+,36?,40-/m1/s1
InChIKey
IFYMEZNJCAQUME-HHBFRJADSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C
XLogP
8.510
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
1
Complexity of molecule
0.313
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
49.690 Å2
Source organisms
Euglena gracilis (Ref.37) - Alga: Euglenoid
Euglena rubida mainx (Ref.42) - Alga: Euglenoid
Oscillatoria limosa (Ref.1) - Cyanobacteria
Averrhoa carambola (Ref.281) - Land plant: starfruit
Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
Corbicula japonica (Ref.221) - Shellfish: bivalve
Corbicula sandai (Ref.221) - Shellfish: bivalve
Corbicula clam (Ref.221) - Shellfish: bivalve
Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
References
  • Ref.37 : N. I. Krinsky, and T. H. Goldsmith, Archives of Biochemistry and Biophysics 91, 271-279 (1960), "The Carotenoids of the Flagellated Alga, Euglena gracilis".
  • Ref.42 : B.Czeczuga, Comp. Biochem. Physiol., 1974, Vol. 48B, pp. 349-354, "Carotenoids in Euglena rubida mainx".
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.281 : Jeana Gross, Raphael Ikan, Gert Eckhardt, Phytochemistry, Volume 22, Issue 6, 1983, Pages 1479-1481, "Carotenoids of the fruit of Averrhoa carambola".
  • Ref.292 : Thomas Wingerath ,Wilhelm Stahl ,Dieter Kirsch, Raimund Kaufmann, and Helmut Sies, J. Agric. Food Chem., 1996, 44 (8), pp 2006–2013, DOI: 10.1021/jf960057y, "Fruit Juice Carotenol Fatty Acid Esters and Carotenoids As Identified by Matrix-Assisted Laser Desorption Ionization (MALDI) Mass Spectrometry".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.609 : Prof. Dr. B. Czeczuga and Doz. Dr. R. Doll, Journal of Botanical Taxonomy and Geobatany, Volume 102, Issue 5-6, pages 431–436, 1991, DOI: 10.1002/fedr.19911020518, "The carotenoid content of lichens of the Cladonia genus from Mecklenburg".
    • CAS
    31661-06-0
    Links to other DB
    KNApSAcK: C00022950
    MassBank: CA000079

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