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Entry
CA00462                                                            

Classification
Carotenoid Name
Echinenone;
β-Carotene-4-one;
β-Echinenone;
beta-Carotene-4-one;
beta-Echinenone;
Myxoxanthine
IUPAC name beta,beta-Caroten-4-one
Formula
C40H54O
Molecular Weight 
550.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective pigment - possible outer membrane-bound UV-B photoprotector (Ref.497).
  • Number of
    conjugated double bonds 
    12 including one ketone (12 in total)
    Number of
    conjugated multiple bonds 
    12 including one ketone (12 in total)
    Isomers 
    InChI
    InChI=1S/C40H54O/c1-30(18-13-20-32(3)23-25-36-34(5)22-15-28-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-37-35(6)38(41)27-29-40(37,9)10/h11-14,16-21,23-26H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+
    InChIKey
    QXNWZXMBUKUYMD-QQGJMDNJSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
    XLogP
    12.761
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.316
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium
    Oscillantoria rubescens (Ref.1) - Cyanobacteria: other name is Planktothrix rubescens
    Oscillatoria agardhii (Ref.1) - Cyanobacteria: other name is Planktothrix agardhii
    Oscillatoria amoena (Ref.1) - Cyanobacteria
    Oscillatoria tenuis (Ref.1) - Cyanobacteria: hot spring alga
    Oscillatoria limosa (Ref.1) - Cyanobacteria
    Oscillatoria princeps (Ref.1) - Cyanobacteria
    Arthrospira sp. (Ref.1) - Cyanobacteria
    Stigonema ocellatum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Stigonema hormoides (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Scytonema crassum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a
    Phormidium ectocarpi (Ref.1) - Cyanobacteria
    Phormidium percicinum (Ref.1) - Cyanobacteria
    Phormidium foveolarum (Ref.1) - Cyanobacteria
    Phormidium lucidum (Ref.1) - Cyanobacteria
    Microcoleus paludosus (Ref.1) - Cyanobacteria
    Microcoleus vaginatus (Ref.1, Ref.5) - Cyanobacteria
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria
    Anabaena cylindrica (Ref.1, Ref.5) - Cyanobacteria: a nitrogen-fixing filamentous cyanobacterium
    Anabaena variabilis (Ref.1, Ref.5) - Cyanobacteria: filamentous cyanobacterium
    Anabaena variabilis ATCC 29413 (Ref.527) - Cyanobacteria
    Anabaena aerulosa oscillatorioides (Ref.1) - Cyanobacteria
    Anabaena flos-aquae (Ref.610) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae
    Cylindrospormum sp. (Ref.1, Ref.5) - Cyanobacteria
    Nostoc sp. (Ref.1, Ref.5) - Cyanobacteria
    Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad
    Tolypothrix tenuis (Ref.1) - Cyanobacteria: filaments repeated single false branched forming cyanobacteria, yellow-brown colored
    Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream
    Mastigocladus laminosus (Ref.1, Ref.5) - Cyanobacteria
    Coccochloris elabens (Ref.1, Ref.5) - Cyanobacteria
    Synechococcus elongatus (Ref.1) - Cyanobacteria: freshwater unicellular cyanobacterium
    Microcystis aeruginosa (Ref.1) - Cyanobacteria
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular
    Synechocystis sp. (Ref.8) - Cyanobacteria
    Aphanizomenon gracile (Ref.8) - Cyanobacteria
    Planktothrix agardhii (Ref.8) - Cyanobacteria
    Microcystis aeruginosa (Ref.8) - Cyanobacteria
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Neochloris wimmeri  - Green alga: Scenedesmaceae
    Ettlia carotinosa (Ref.16) - Green alga: Chlamydomonadales
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
    Scenedesmus vacuolatus (Ref.16) - Green alga: Scenedesmaceae
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Isochrysis galbana (Ref.31) - Alga: Haptophyte
    Skeletonema costatum (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Euglena gracilis (Ref.37, Ref.38, Ref.40, Ref.8) - Alga: Euglenoid
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglenoid
    Xanthophyllomyces dendrorhous (Ref.204) - Fungi: red yeast
    Gelliodes callista (Ref.253) - Sea sponge
    Gloeobacter violaceus PCC 7421 (Ref.266) - Cyanobacteria: rod-shape unicellular cyanobacterium, diverged very early during the evolution of cyanobacteria
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Botryococcus braunii Kawaguchi-1 (Ref.231) - Green alga: Trebouxiophyceae
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell
    Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo
    Clione limacina (Ref.635) - gastropods
    Paedoclione doliiformis (Ref.635) - gastropods
    References
  • Ref.449 : Kleinig, Hans; Heumann, Wolfram; Meister, Walter; Englert, Gerhard, Helvetica Chimica Acta (1979), 62(8), 2551-7., "Carotenoids of Rhizobia.  I.  New carotenoids from Rhizobium lupini".
  • 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.603 : M Lakatos, W Bilger, B Büdel, Eur. J. Phycol. (2001), 36: 367–375., "Carotenoid composition of terrestrial Cyanobacteria: response to natural light conditions in open rock habitats in Venezuela".
  • Ref.5 : T. W. Goodwin, J. gen. Microbiol. 17, 467-473 (1957), "The nature and distribution of Carotenoids in some Blue-Green Algae".
  • Ref.527 : Shinichi Takaichi, Mari Mochimaru, and Takashi Maoka, Plant Cell Physiol. 47(2): 211–216 (2006), doi:10.1093/pcp/pci236, "Presence of Free Myxol and 4-Hydroxymyxol and Absence of Myxol Glycosides in Anabaena variabilis ATCC 29413, and Proposal of a Biosynthetic Pathway of Carotenoids".
  • Ref.610 : The Biochemistry of the Carotenoids: Volume I Plants, p.237, Springer, ISBN-10: 9400958625, ISBN-13: 978-9400958623.
  • Ref.8 : L. Schlueter, T. L. Lauridsen, G. Krogh, and Joergensen, Freshwater Biology, 2006, 51, 1474-1485 " Identification and quantification of phytoplankton groups in lakes using new pigment ratios – a comparison between pigment analysis by HPLC and microscopy".
  • Ref.12 : N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13 : PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14 : S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • 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.19 : Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • 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.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.36 : F. Pennington, R. R. L. Guillard and S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol.16, No.7/8, pp. 589-592, 1988, "Carotenoid Distribution Patterns in Bacillariophyceae (Diatoms)".
  • 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.38 : D. V. Heelis, W. Kernick, G. O. Philips, and K. Davies, Arch. Microbiol. 121, 207-211 (1979), "Separation and Identification of the Carotenoid Pigments of Stigmata Isolated from Light Grown Cells of Euglena gracilis Strain Z".
  • Ref.40 : 細谷圭助、北岡正三郎、日本栄養•食糧学会誌 Vol. 37, No. 6, 519-524, 1984 「Euglena gracilis Z におけるプロビタミンAの高速液体クロマトグラフによる定量および培養条件による変動」.
  • Ref.41 : N. I. Krinsky, A. Gordon, and A. I. Stern, Plant Physiol 39: 441-445 1964, "The appearance of Neoxanthin during the Regreenin g of Dark-grown Euglena".
  • Ref.204 : Tani C, Maoka T, Tani M, Moritomo Y, Okada T, Kitahara G, Katamoto H., J Oleo Sci. 2014;63(9):943-51. Epub 2014 Aug 5., "Accumulation of xanthophylls from the phaffia yeast (Xanthophyllomyces dendrorhrous) in calves.".
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.266 : Tsuchiya T, Takaichi S, Misawa N, Maoka T, Miyashita H, Mimuro M., FEBS Lett. 2005 Apr 11;579(10):2125-9., "The cyanobacterium Gloeobacter violaceus PCC 7421 uses bacterial-type phytoene desaturase in carotenoid biosynthesis.".
  • 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.231 : Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok, Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok., "Isolation and HPLC method development of azafrin from Alectra parasitica var. chitrakutensis".
  • Ref.421 : Pinky Baruah and Goswami UC., Journal of Research in Biology, pp.114-118, 2012, Vol.2, No.2, "Characterization of carotenoid pigments in amphibian, Rhacophorous bipunctatus".
  • Ref.442 : Kiyoshi Katagiri, Takashi Maoka, Takao Matsuno, COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. B, COMPARATIVE BIOCHEMISTRY, 84(4):473-476 · JANUARY 1986, "Carotenoids of shell fishes-VIII. Comparative biochemical studies of carotenoids in three species of spindleshell, Fusinus perplexus, F.p. ferrugineus and F. forceps".
  • Ref.471 : Denis L Fox, Thomas S Hopkins, Comparative Biochemistry and Physiology, Volume 17, Issue 3, March 1966, Pages 841–856, "Comparative metabolic fractionation of carotenoids in three flamingo species".
  • Ref.635 : Takashi Maoka, Takashi Kuwahara, and Masanao Narita, Mar. Drugs 2014, 12, 1460-1470, "Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain", doi:10.3390/md12031460.
  • Ref.497 : Ehling-Schulz, Bilger W, Scherer S., J Bacteriol. 1997 Mar;179(6):1940-5., "UV-B-induced synthesis of photoprotective pigments and extracellular polysaccharides in the terrestrial cyanobacterium Nostoc commune.".
  • CAS
    432-68-8
    Links to other DB
    KEGG COMPOUND: C08592
    LipidBank: VCA0058
    MassBank: CA000149
    ProCarDB: C1921

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