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Entry |
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Classification |
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Carotenoid Name
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Lutein epoxide;
Lutein-epoxide;
Lutein 5,6-epoxide;
Taraxanthin;
Isolutein
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IUPAC name |
(3S,5R,6S,3'R,6'R)-5,6-Epoxy-5,6-dihydro-beta,epsilon-carotene-3,3'-diol
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Formula |
C40H56O3
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Molecular Weight |
584.848 g/mol
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Structure |
Search similar carotenoids
Mol file
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Carotenoid DB Fingerprints |
Predict biological activities of this carotenoid
(3S,5R,6S,3'R,6'R), 5,6+H, 3-OH, 3'-OH, 5,6-Epoxy, beta,epsilon
( Help )
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Biological functions/Properties |
Photosynthetic pigment of higher plants (Ref.503).
Xanthophyll cycle pigment (Ref.470).
Yellow pigment (Ref.468).
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Number of
conjugated double bonds |
9
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Number of
conjugated multiple bonds |
9
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Isomers |
Constitutional isomer: CA00227, CA00228, CA00394, CA00340, CA00377, CA00378, CA00339, CA00342, CA00338, CA00341, CA00410, CA00436, CA00437, CA00407, CA00408, CA00412, CA00438, CA00411, CA00409, CA00583, CA00607, CA00606, CA00609, CA00608, CA00618, CA00630, CA00624, CA00625, CA01047, CA00761, CA00762, CA00739
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InChI |
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InChIKey |
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Canonical SMILES |
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XLogP |
10.483
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Hydrogen Bond donors
(Lipinski's definition) |
2
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Hydrogen Bond Acceptors
(Lipinski's definition) |
3
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| LipinskiFailures |
1
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| Complexity of molecule |
0.313
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| Number of heavy atoms |
43
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TPSA
(Topological Polar Surface Area) |
52.990 Å2
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Reaction |
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Pathway |
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Major carotenoid information |
Major carotenoid in dandelion (Ref.713) and chrysanthemum (Ref.736) flowers.
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Minor carotenoid information |
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Source organisms |
Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes (Ascomycota - Cladoniaceae)
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References |
Ref.16: M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
Ref.17: H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
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".
Ref.503: Javier de las Rivas, Anunciacion Abadia, and Javier Abadia, Plant Physiol. (1989) 91, 190-192, “A New Reversed Phase-HPLC Method Resolving All Major Higher Plant Photosynthetic Pigments1”.
Ref.470: Esteban R1, Jiménez ET, Jiménez MS, Morales D, Hormaetxe K, Becerril JM, García-Plazaola JI., Tree Physiol. 2007 Oct;27(10):1407-14., "Dynamics of violaxanthin and lutein epoxide xanthophyll cycles in Lauraceae tree species under field conditions.".
Ref.468: Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
Ref.713: Antonio J. Meléndez-Martíneza, George Britton, Isabel M.Vicario, Francisco J. Heredia, Phytochemistry, Volume 67, Issue 8, April 2006, Pages 771-777, "HPLC analysis of geometrical isomers of lutein epoxide isolated from dandelion (Taraxacum officinale F. Weber ex Wiggers)", https://doi.org/10.1016/j.phytochem.2006.02.002.
Ref.736: Hui Yuan et al., Horticulture Research volume 2, Article number: 15036 (2015), "Carotenoid metabolism and regulation in horticultural crops".
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CAS |
28368-08-3
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Links to other DB |
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