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Entry
CA00923                                                            

Classification
Carotenoid Name
Bacterioruberin;
BR
IUPAC name (2S,2'S)-2,2'-Bis-(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetrahydro-1,2,1',2'-tetrahydro-psi,psi-carotene-1,1'-diol
Formula
C50H76O4
Molecular Weight 
741.108 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antioxidant activity - much better radical scavenger than that of β-carotene as it contains 13 pairs of conjugated double bonds (Ref.575, Ref.576).
  • Also resist from H2O2 exposure (Ref.577, Ref.578).
  • Photoprotective activity - resist oxidative DNA damage from UV irradiation (Ref.577, Ref.578).
  • Radio protective activity - resist oxidative DNA damage from gamma irradiation (Ref.577, Ref.578).
  • Number of
    conjugated double bonds 
    13
    Number of
    conjugated multiple bonds 
    13
    Isomers 
    InChI
    InChI=1S/C50H76O4/c1-39(23-17-25-41(3)27-19-29-43(5)31-33-45(49(11,12)53)35-37-47(7,8)51)21-15-16-22-40(2)24-18-26-42(4)28-20-30-44(6)32-34-46(50(13,14)54)36-38-48(9,10)52/h15-34,45-46,51-54H,35-38H2,1-14H3/b16-15+,23-17+,24-18+,27-19+,28-20+,33-31+,34-32+,39-21+,40-22+,41-25+,42-26+,43-29+,44-30+/t45-,46-/m1/s1
    InChIKey
    UVCQMCCIAHQDAF-RNTVPSGKSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\C=C\[C@@H](C(O)(C)C)CCC(O)(C)C)/C)/C)/C)/C=C/C=C(/C=C/C=C(/C=C/[C@@H](C(O)(C)C)CCC(O)(C)C)\C)\C
    XLogP
    13.650
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    54
    TPSA
    (Topological Polar Surface Area) 
    80.920 Å2
    Source organisms
    Halobacterium strain SP-2 (Ref.332) - Archaea: Euryarchaeota
    Halorubrum strain SP-4 (Ref.332) - Archaea: Euryarchaeota
    Halorubrum chaoviator Halo-G (Ref.333) - Archaea: Euryarchaeota
    Halococcus morrhuae (Ref.389) - Archaea: Euryarchaeota
    Halobacterium salinarium (Ref.389) - Archaea: Euryarchaeota
    Haloarcula japonica (Ref.621) - Archaea: Euryarchaeota, triangular, disc-shaped, extremely halophilic archaeon that requires high concentrations of NaCl for growth
    Micrococcus roseus (Ref.387) - Actinobacteria
    References
  • Ref.332 : SUI Liying, LIU Liangsen, DENG Yuangao, Chinese Journal of Oceanology and Limnology, Vol. 32 No. 6, P. 1280-1287, 2014, "Characterization of halophilic C50 carotenoid-producing archaea isolated from solar saltworks in Bohai Bay, China".
  • Ref.333 : Davood Naziri, Masoud Hamidi, Salar Hassanzadeh, Vahideh Tarhriz, Bahram Maleki Zanjani, Hossein Nazemyieh, Mohammd Amin Hejazi, Mohammad Saeid Hejazi, Advanced Pharmaceutical Bulletin, 2014, 4(1), 61-67, "Analysis of Carotenoid Production by Halorubrum sp. TBZ126; an Extremely Halophilic Archeon from Urmia Lake".
  • Ref.389 : Mandelli, Fernanda; Miranda, Viviane S.; Rodrigues, Eliseu; Mercadante, Adriana Z., World Journal of Microbiology & Biotechnology (2012), 28(4), 1781-1790., "Identification of carotenoids with high antioxidant capacity produced by extremophile microorganisms".
  • Ref.621 : Ying Yang, Rie Yatsunami, Ai Ando, Nobuhiro Miyoko, Toshiaki Fukui, Shinichi Takaichi, Satoshi Nakamura, "Complete Biosynthetic Pathway of the C50 Carotenoid Bacterioruberin from Lycopene in the Extremely Halophilic Archaeon Haloarcula japonica", Journal of Bacteriology, May 2015 Volume 197 Number 9.
  • Ref.387 : Strand, Aase; Shivaji, Sisinthy; Liaaen-Jensen, Synnove, Biochemical Systematics and Ecology (1997), 25(6), 547-552., "Bacterial carotenoids 55. C50-carotenoids 25. Revised structures of carotenoids associated with membranes in psychrotrophic Micrococcus roseus".
  • Ref.575 : Yatsunami, R.; Ando, A.; Yang, Y.; Takaichi, S.; Kohno, M.; Matsumura, Y.; Ikeda, H.; Fukui, T.; Nakasone, K.; Fujita, N.; et al. Identification of carotenoids from the extremely halophilic archaeon Haloarcula japonica. Front. Microbiol. 2014, 5, 100–105..
  • Ref.576 : Saito, T.; Miyabe, Y.; Ide, H.; Yamamoto, O. Hydroxyl radical scavenging ability of bacterioruberin. Radiat. Phys. Chem. 1997, 50, 267–269..
  • Ref.577 : Shahmohammadi, H.R.; Asgarani, E.; Terato, H.; Saito, T.; Ohyama, Y.; Gekko, K.; Yamamoto, O.; Ide, H. Protective roles of bacterioruberin and intracellular KCl in the resistance of Halobacterium salinarium against DNA-damaging agents. J. Radiat. Res. 1998, 39, 251–262..
  • Ref.578 : Kottemann, M.; Kish, A.; Iloanusi, C.; Bjork, S.; DiRuggiero, J. Physiological responses of the halophilic archaeon Halobacterium sp. strain NRC1 to desiccation and gamma irradiation. Extremophiles 2005, 9, 219–227..
  • CAS
    32719-43-0
    Links to other DB
    KNApSAcK: C00023099
    ProCarDB: C1753

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