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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   
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
InChI=1S/C40H52O3/c1-28(17-13-19-30(3)21-23-34-32(5)36(41)25-26-39(34,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-35-33(6)38(43)37(42)27-40(35,9)10/h11-24,37,42H,25-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t37-/m0/s1
InChIKey
OOUTWVMJGMVRQF-NWYYEFBESA-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)C(=O)[C@H](CC1(C)C)O)\C
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
Source organisms
Rhizobium lupini (Ref.449) - Alphaproteobacteria: root nodule bacterium
Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
Euglena sanguinea (Ref.43) - Alga: Euglenoid
Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog
Fusinus perplexus (Ref.442) - Shellfish: univalve shell
Oriolus cruentus (Ref.444) - Bird: oriole
Euchaeta russelli (Ref.450) - Crustacean: copepod
Phoenicoparrus andinus (Ref.471) - Bird: Andean flamingo
Phoenicoparrus jamesi (Ref.471) - Bird: Puna flamingo
Phoenicoparrus ruber (Ref.471) - Bird: American flamingo
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".
  • CAS
    4418-72-8
    Links to other DB
    KEGG COMPOUND: C15967
    KNApSAcK: C00000929
    LipidBank: VCA1014
    MassBank: CA000140
    ProCarDB: C1926

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