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Entry
CA00411                                                            

Classification
Carotenoid Name
Cryptoxanthin diepoxide;
Cryptoxanthin 5,6:5',6'-diepoxide
IUPAC name 5,6:5',6'-Diepoxy-5,6,5',6'-tetrahydro-beta,beta-caroten-3-ol
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/c1-30(18-13-20-32(3)22-26-39-35(5,6)24-15-25-37(39,9)42-39)16-11-12-17-31(2)19-14-21-33(4)23-27-40-36(7,8)28-34(41)29-38(40,10)43-40/h11-14,16-23,26-27,34,41H,15,24-25,28-29H2,1-10H3/b12-11+,18-13+,19-14+,26-22+,27-23+,30-16+,31-17+,32-20+,33-21+
InChIKey
ONQKWANDXQNLEJ-CGYYJCQDSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C12OC2(C)CCCC1(C)C)/C)/C)/C=C/C=C(/C=C/C12OC2(C)CC(CC1(C)C)O)\C
XLogP
9.994
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
1
Complexity of molecule
0.323
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
45.290 Å2
Source organisms
Pavlova lutheri (Ref.31) - Alga: Haptophyte
Prymnesium parvum (Ref.31) - Alga: Haptophyte
Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
References
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.27 : N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28 : Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • 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".
  • CAS
    2086-87-5
    Links to other DB
    KNApSAcK: C00022953
    MassBank: CA000043

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