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Entry
CA00150                                                            

Classification
Carotenoid Name
Lycopene 5,6-epoxide
IUPAC name 5,6-Epoxy-5,6-dihydro-psi,psi-carotene
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10
Number of
conjugated multiple bonds 
10
Isomers 
InChI
InChI=1S/C40H56O/c1-32(2)18-13-22-36(7)25-15-27-37(8)26-14-23-34(5)20-11-12-21-35(6)24-16-28-38(9)29-30-39-40(10,41-39)31-17-19-33(3)4/h11-12,14-16,18-21,23-30,39H,13,17,22,31H2,1-10H3/b12-11+,23-14+,24-16+,27-15+,30-29+,34-20+,35-21+,36-25+,37-26+,38-28+
InChIKey
KAOPTJGOSUTKJR-RGZXCSNFSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1OC1(C)CCC=C(C)C)/C)/C)/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C
XLogP
13.343
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
2
Complexity of molecule
0.031
Number of heavy atoms
41
TPSA
(Topological Polar Surface Area) 
12.530 Å2
Source organisms
Discina reticulata (Ref.115) - Fungi: mushroom
Discina ancilis (Ref.115) - Fungi: mushroom
Lycopersicon esculentum  - Land plant: Solanaceae: tomato
Oxidation of lycopene with m-chloroperbenzoic acid (Ref.345) - Oxidation of lycopene with m-chloroperbenzoic acid
Protousnea sp. (Ref.388) - Fungi: lichen
Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
References
  • Ref.115 : Czeczuga, B., Phyton (Horn, Austria) (1979), 19(3-4), 225-32., "Investigations on carotenoids in fungi. VI. Representatives of the Helvellaceae and Morchellaceae".
  • Ref.345 : Khachik, Frederick; Pfander, Hanspeter; Traber, Bruno, Journal of Agricultural and Food Chemistry (1998), 46(12), 4885-4890., "Proposed Mechanisms for the Formation of Synthetic and Naturally Occurring Metabolites of Lycopene in Tomato Products and Human Serum".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • 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
    51599-10-1
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