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Entry
CA00489                                                            

Classification
Carotenoid Name
Adonixanthin;
Doradexanthin;
beta-Doradexanthin;
3,3'-Dihydroxyechinenone;
β-Doradexanthin;
all-trans-β-Doradexanthin;
all-trans-beta-Doradexanthin;
4-ketozeaxanthin
IUPAC name (3S,3'R)-3,3'-Dihydroxy-beta,beta-caroten-4-one
Formula
C40H54O3
Molecular Weight 
582.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
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/C40H54O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)26-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)38(43)37(42)27-40(36,9)10/h11-24,34,37,41-42H,25-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t34-,37+/m1/s1
InChIKey
YECXHLPYMXGEBI-ZNQVSPAOSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C
XLogP
10.130
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
1
Complexity of molecule
0.309
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
57.530 Å2
Source organisms
Gelliodes callista (Ref.253) - Sea sponge
Protousnea sp. (Ref.388) - Fungi: lichen
Euchaeta russelli (Ref.450) - Crustacean: copepod
Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
Paedoclione doliiformis (Ref.635) - gastropods
References
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • 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.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.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.
  • CAS
    4418-73-9
    Links to other DB
    KEGG COMPOUND: C15968
    KNApSAcK: C00000917
    LipidBank: VCA0014
    ProCarDB: C1927

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