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Entry
CA00942                                                            
Classification
Carotenoid Name
Sarcinaxanthin
IUPAC name (2R,6R,2'R,6'R)-2,2'-Bis-(4-hydroxy-3-methylbut-2-enyl)-gamma,gamma-carotene
Formula
C50H72O2
Molecular Weight 
705.076 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI

InChIKey

Canonical SMILES

XLogP
15.700
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.242
Number of heavy atoms
52
TPSA
(Topological Polar Surface Area) 
40.460 Å2
Reaction
  • Substrate: CR00302
  • Product: CR00378
    • Pathway
  • Pathway: CB000101
    • Major carotenoid information
    Major carotenoid in Micrococcus luteus (Ref.738).
    Minor carotenoid information

    Source organisms
    Sarcina lutea (Ref.241) - Firmicutes - Clostridia (Firmicutes - Clostridiaceae)
    Micrococcus luteus (Ref.240, Ref.384) - Actinobacteria: normal inhabitant of human, same as Micrococcus lysodeikticus (Actinobacteria - Micrococcaceae)
    Micrococcus yunnanensis (Ref.385) - Actinobacteria: isolated from surface-sterilized Polyspora axillaris roots (Actinobacteria - Micrococcaceae)
    References
  • Ref.241: Hertzberg, Sissel; Liaaen-Jensen, Synnoeve, Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1977), 31(3), 215-18., "Bacterial carotenoids. LIII. C50-Carotenoids. 19. Absolute configuration of sarcinaxanthin and sarcinaxanthin mono-β-D-glucoside. Isolation of sarcinaxanthin diglycoside".
  • Ref.240: Goksoeyr, Audun, PCT Int. Appl. (2011), WO 2011151426 A2 20111208., "Cloning, sequencing and characterization of gene cluster resposnible for sarcinaxanthin biosynthesis in Micrococcus luteus and use of related carotenoids in sunscreen and photoprotective compositions".
  • Ref.384: Netzer, Roman; Brautaset, Trygve; Bruheim, Per, PCT Int. Appl. (2011), WO 2011151425 A1 20111208., "Discovery and cloning of a sarcinaxanthin biosynthesis gene cluster in Micrococcus luteus".
  • Ref.385: Osawa, Ayako; Ishii, Yoko; Sasamura, Nao; Morita, Marie; Kasai, Hiroaki; Maoka, Takashi; Shindo, Kazutoshi, Journal of Oleo Science (2010), 59(12), 653-659., "Characterization and antioxidative activities of rare C50 carotenoids, sarcinaxanthin, sarcinaxanthin monoglucoside, and sarcinaxanthin diglucoside, obtained from Micrococcus yunnanensis".
  • Ref.738: Roman Netzer, Marit H. Stafsnes, Trygve Andreassen, Audun Goksøyr, Per Bruheim, Trygve Brautaset, "Biosynthetic Pathway for γ-Cyclic Sarcinaxanthin in Micrococcus luteus: Heterologous Expression and Evidence for Diverse and Multiple Catalytic Functions of C50 Carotenoid Cyclases".
    • CAS
    11031-47-3
    Links to other DB
    KNApSAcK: C00023086
    MassBank: CA000128

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