Carotenoids obi
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Carotenoids DB          Carotenoids DB: CA00487   
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Entry
CA00487                                                            
Classification
Carotenoid Name
Adonirubin;
Phoenicoxanthin;
(3S)-Phoenicoxanthin
IUPAC name (3S)-3-Hydroxy-beta,beta-carotene-4,4'-dione
Formula
C40H52O3
Molecular Weight 
580.816 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including two ketones (13 in total)
Number of
conjugated multiple bonds 
13 including two ketones (13 in total)
Isomers 
InChI

InChIKey

Canonical SMILES

XLogP
10.242
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
1
Complexity of molecule
0.316
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
54.370 Å2
Reaction
  • Substrate: CR00187
  • Product: CR00185,  CR00244,  CR00256
    • Pathway
  • Pathway: CB000056,  CB000057
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium (Alphaproteobacteria - Rhizobiaceae)
    Euglena sanguinea (Ref.43) - Alga: Euglena (Euglenida - Euglenaceae)
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate ((Alveolata) - Tovelliaceae)
    Euchaeta russelli (Ref.450) - Crustacean: copepod (Arthropoda - Euchaetidae)
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell (Mollusca - Fasciolariidae)
    Plesiocolochirus minutus (Ref.763) - sea cucumber (Echinodermata - Cucumariidae)
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog (Chordata - Rhacophoridae)
    Phoenicoparrus andinus (Ref.471) - Bird: Andean flamingo (Chordata - Phoenicopteridae)
    Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo (Chordata - Phoenicopteridae)
    Phoenicoparrus ruber (Ref.471) - Bird: American flamingo (Chordata - Phoenicopteridae)
    Oriolus cruentus (Ref.444) - Bird: oriole (Chordata - Corvidae)
    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.34: R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • Ref.43: Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".
  • 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.444: LaFountain, Amy M.; Frank, Harry A.; Prum, Richard O., Archives of Biochemistry and Biophysics (2013), 539(2), 126-132., "Carotenoids from the crimson and maroon plumages of Old World orioles (Oriolidae)".
  • Ref.450: Bandaranayake, Wickramasinghe M.; Gentien, Patrick, Comparative Biochemistry and Physiology, Part B: Biochemistry & Molecular Biology (1982), 72B(3), 409-14., "Carotenoids of Temora turbinata, Centropages furcatus, Undinula vulgaris, and Euchaeta russelli".
  • 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.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”.
    • CAS
    4418-72-8
    Links to other DB
    KEGG COMPOUND: C15967
    KNApSAcK: C00000929
    LipidBank: VCA1014
    MassBank: CA000140
    ProCarDB: C1926

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