Carotenoids obi
All carotenoids     All organisms     All pathways     All reactions     Feedback
Carotenoids DB          Carotenoids DB: CA00462   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible biosynthetic routes of this carotenoid   ]
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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00183,  CR00186,  CR00241
  • Product: CR00234
    • Pathway
  • Pathway: CB000055,  CB000106,  CB000056,  CB000061,  CB000062
    • Major carotenoid information
    Major carotenoid in Anabaena spp., Nostoc sp., and Synechocystis sp. PCC 6803 (Ref.732).
    Minor carotenoid information
    Minor carotenoid in some prochlorophytes and cyanobacteria e.g. Gloeobacter violaceus PCC 7421 (Ref.707, Ref.266).
    Source organisms
    Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium (Alphaproteobacteria - Rhizobiaceae)
    Synechocystis sp. (Ref.8) - Cyanobacteria (Cyanobacteria - Merismopediaceae)
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular (Cyanobacteria - Merismopediaceae)
    Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream (Cyanobacteria - Rivulariaceae)
    Synechococcus elongatus (Ref.1) - Cyanobacteria: freshwater unicellular cyanobacterium (Cyanobacteria - Synechococcaceae)
    Arthrospira sp. (Ref.1) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Microcoleus paludosus (Ref.1) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Microcoleus vaginatus (Ref.1, Ref.5) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Oscillantoria rubescens (Ref.1) - Cyanobacteria: other name is Planktothrix rubescens (Cyanobacteria - Microcoleaceae)
    Oscillatoria agardhii (Ref.1) - Cyanobacteria: other name is Planktothrix agardhii (Cyanobacteria - Microcoleaceae)
    Planktothrix agardhii (Ref.8) - Cyanobacteria (Cyanobacteria - Microcoleaceae)
    Microcystis aeruginosa (Ref.8) - Cyanobacteria (Cyanobacteria - Microcystaceae)
    Coccochloris elabens (Ref.1, Ref.5) - Cyanobacteria (Cyanobacteria - Aphanothecaceae)
    Aphanizomenon gracile (Ref.8) - Cyanobacteria (Cyanobacteria - Aphanizomenonaceae)
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria (Cyanobacteria - Aphanizomenonaceae)
    Mastigocladus laminosus (Ref.1, Ref.5) - Cyanobacteria (Cyanobacteria - Hapalosiphonaceae)
    Anabaena aerulosa oscillatorioides (Ref.1) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Anabaena cylindrica (Ref.1, Ref.5) - Cyanobacteria: a nitrogen-fixing filamentous cyanobacterium (Cyanobacteria - Nostocaceae)
    Anabaena flos-aquae (Ref.610) - Cyanobacteria: filamentous cyanobacterium same as Dolichospermum flos-aquae (Cyanobacteria - Aphanizomenonaceae)
    Anabaena variabilis (Ref.1, Ref.5) - Cyanobacteria: filamentous cyanobacterium (Cyanobacteria - Nostocaceae)
    Anabaena variabilis ATCC 29413 (Ref.527) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Cylindrospormum sp. (Ref.1, Ref.5) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad (Cyanobacteria - Nostocaceae)
    Nostoc sp. (Ref.1, Ref.5) - Cyanobacteria (Cyanobacteria - Nostocaceae)
    Stigonema ocellatum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Stigonemataceae)
    Stigonema hormoides (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Stigonemataceae)
    Scytonema crassum (Ref.603) - Cyanobacteria: terrestrial cyanobacteria sampled from rock surfaces containing chlorophyll a (Cyanobacteria - Scytonemataceae)
    Oscillatoria amoena (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Oscillatoria limosa (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Oscillatoria princeps (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Oscillatoria tenuis (Ref.1) - Cyanobacteria: hot spring alga (Cyanobacteria - Oscillatoriaceae)
    Phormidium ectocarpi (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Phormidium foveolarum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Phormidium lucidum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Phormidium percicinum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Tolypothrix tenuis (Ref.1) - Cyanobacteria: filaments repeated single false branched forming cyanobacteria, yellow-brown colored (Cyanobacteria - Tolypothrichaceae)
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
    Ettlia carotinosa (Ref.16) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Neochloris wimmeri  - Green alga: Scenedesmaceae (Chlorophyta - Neochloridaceae)
    Scenedesmus vacuolatus (Ref.16) - Green alga: Scenedesmaceae (Chlorophyta - Scenedesmaceae)
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    Botryococcus braunii Kawaguchi-1 (Ref.231) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena gracilis (Ref.37, Ref.38, Ref.40, Ref.8) - Alga: Euglena (Euglenida - Euglenaceae)
    Isochrysis galbana (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Isochrysidaceae)
    Navicula pelliculosa (Ref.36) - Alga: Diatom (Bacillariophyta - Naviculaceae)
    Skeletonema costatum (Ref.36) - Alga: Diatom (Bacillariophyta - Skeletonemataceae)
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Xanthophyllomyces dendrorhous (Ref.204) - Fungi: red yeast (Basidiomycota - Cystofilobasidiaceae)
    Corbicula clams (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula japonica (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula sandai (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell (Mollusca - Fasciolariidae)
    Clione limacina (Ref.635) - gastropods (Mollusca - Clionidae)
    Paedoclione doliiformis (Ref.635) - gastropods (Mollusca - Clionidae)
    Gelliodes callista (Ref.253) - Sea sponge (Porifera - Niphatiidae)
    Plesiocolochirus minutus (Ref.763) - sea cucumber (Echinodermata - Cucumariidae)
    Gymnogobius castaneus (Ref.772) - Bony fish: Rosary goby, small goby（4～6 cm body length）that inhabits the middle stretches of rivers, lakes, and lagoons in North Eastern Japan. Its tail fin is bright orange in color. (Chordata - Gobiidae)
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog (Chordata - Rhacophoridae)
    Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo (Chordata - Phoenicopteridae)
    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.763: Takashi Maoka, Syu Nakachi, Ryouhei Kobayashi, Miho Mori, Yoshikazu Sakagami, / Tetrahedron Letters 56 (2015) 5954–5955, http://dx.doi.org/10.1016/j.tetlet.2015.09.060, “A new carotenoid, 9Z,9'Z-tetrahydroastaxanthin, from the sea cucumber Plesiocolochirus minutus”.
  • Ref.772: Takashi Maoka, J. Oleo Sci. 67, (10) 1259-1263 (2018), “New Acetylenic Carotenoid 6’-Epimonadoxanthin from the Rosary Goby Gymnogobius castaneus”, doi: 10.5650/jos.ess18153.
  • 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.".
  • Ref.732: S. Takaichia and M. Mochimaru, Cell. Mol. Life Sci. 64 (2007) 2607 – 2619, "Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides", DOI 10.1007/s00018-007-7190-z.
  • Ref.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.
    • CAS
    432-68-8
    Links to other DB
    KEGG COMPOUND: C08592
    LipidBank: VCA0058
    MassBank: CA000149
    ProCarDB: C1921

       Searching other references with Google Scholar or searching the colour of this carotenoid by Google image search