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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   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI
InChI=1S/C50H72O2/c1-37(19-15-21-39(3)25-33-47-43(7)27-31-45(49(47,9)10)29-23-41(5)35-51)17-13-14-18-38(2)20-16-22-40(4)26-34-48-44(8)28-32-46(50(48,11)12)30-24-42(6)36-52/h13-26,33-34,45-48,51-52H,7-8,27-32,35-36H2,1-6,9-12H3/b14-13+,19-15+,20-16+,33-25+,34-26+,37-17+,38-18+,39-21+,40-22+,41-23+,42-24+/t45-,46-,47+,48+/m0/s1
InChIKey
XFXHBQLETDDGGF-XUYZKQIISA-N
Canonical SMILES
OC/C(=C/C[C@H]1CCC(=C)[C@H](C1(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]1C(=C)CC[C@@H](C1(C)C)C/C=C(/CO)\C)\C)\C)/C)/C)/C
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
Source organisms
Sarcina lutea (Ref.241) - Firmicutes - Clostridia
Micrococcus luteus (Ref.240, Ref.384) - Actinobacteria: normal inhabitant of human, same as Micrococcus lysodeikticus
Micrococcus yunnanensis (Ref.385) - Actinobacteria: isolated from surface-sterilized Polyspora axillaris roots
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".
  • CAS
    11031-47-3
    Links to other DB
    KNApSAcK: C00023086
    MassBank: CA000128

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