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Entry
CA00770                                                            

Classification
Carotenoid Name
Isorenieratene;
Streptoxanthin;
Leprotene;
Leprotin
IUPAC name phi,phi-Carotene
Formula
C40H48
Molecular Weight 
528.784 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity (Ref.491).
  • Number of
    conjugated double bonds 
    15
    Number of
    conjugated multiple bonds 
    15
    Isomers 
  • Constitutional isomer: CA00308, CA00778, CA00781
  • Cis/trans isomer: CA00771, CA00772
  • InChI
    InChI=1S/C40H48/c1-29(17-13-19-31(3)21-27-39-35(7)25-23-33(5)37(39)9)15-11-12-16-30(2)18-14-20-32(4)22-28-40-36(8)26-24-34(6)38(40)10/h11-28H,1-10H3/b12-11+,17-13+,18-14+,27-21+,28-22+,29-15+,30-16+,31-19+,32-20+
    InChIKey
    ZCIHMQAPACOQHT-YSEOPJLNSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\c1c(C)ccc(c1C)C)/C)/C)/C=C/C=C(/C=C/c1c(C)ccc(c1C)C)\C
    XLogP
    17.704
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    1
    Complexity of molecule
    0.341
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Streptomyces coelicolor (Ref.89, Ref.91) - Actinobacteria
    Streptomyces griseus (Ref.179) - Actinobacteria
    Brevibacterium linens ATCC 9175 (Ref.85, Ref.90, Ref.178) - Actinobacteria: Limberger cheese ripening bacteria
    Chlorobium phaeobacteroides (Ref.92) - Green sulfur bacteria
    Chlorobium phaeobacteroides strain CL1401 (Ref.93) - Green sulfur bacteria
    Reniera japonica (Ref.95, Ref.184) - Sea sponge
    Polymastia granulosa (Ref.96) - Sea sponge
    Suberites sericeus (Ref.97) - Sea sponge
    Hymeniacidon penicillata (Ref.98) - Sea sponge
    Tedania digitata (Ref.98) - Sea sponge
    Agelas schmidtii (Ref.99) - Sea sponge
    Axinella verrucosa (Ref.100) - Sea sponge
    Mycobacterium kansasii (Ref.101) - Actinobacteria
    Dendrodoris fulva (Ref.102) - Gastropod
    Doriopsilla albopunctata (Ref.102) - Gastropod
    Anisodoris nobilis (Ref.102) - Gastropod
    Streptomyces mediolani (Ref.87, Ref.88) - Actinobacteria
    Mycobacterium phlei (Ref.103) - Actinobacteria
    Chromatiaceae spp. (Ref.148) - purple sulfur bacteria
    Pelochromatium roseum (Ref.94) - purple sulfur bacteria
    Pelochromatium selenoides (Ref.94) - purple sulfur bacteria
    Chlorochromatium lunatum (Ref.94) - unclassified bacteria
    Agelas schmidtii (Ref.369) - Sea sponge
    References
  • Ref.89 : Gao, Chan; Hindra; Mulder, David; Yin, Charles; Elliot, Marie A., mBio (2012), 3(6), e00407-12. "Crp is a global regulator of antibiotic production in Streptomyces".
  • Ref.91 : Takano, Hideaki; Obitsu, Saemi; Beppu, Teruhiko; Ueda, Kenji, Journal of Bacteriology (2005), 187(5), 1825-1832., "Light-​induced carotenogenesis in Streptomyces coelicolor A3(2)​: identification of an extracytoplasmic function sigma factor that directs photodependent transcription of the carotenoid biosynthesis gene cluster".
  • Ref.179 : Krugel, Hans; Krubasik, Philipp; Weber, Kerstin; Saluz, Hans Peter; Sandmann, Gerhard, Biochimica et Biophysica Acta, Molecular and Cell Biology of Lipids (1999), 1439(1), 57-64., "Functional analysis of genes from Streptomyces griseus involved in the synthesis of isorenieratene, a carotenoid with aromatic end groups, revealed a novel type of carotenoid desaturase".
  • Ref.85 : Kohl, Werner; Achenbach, Hans; Reichenbach, Hans, Phytochemistry (Elsevier) (1983), 22(1), 207-10., "Investigations on metabolites of microorganisms. Part 24. The pigments of Brevibacterium linens: aromatic carotenoids".
  • Ref.90 : Dufosse, L.; de Echanove, M. C., Food Research International (2005), 38(8-9), 967-973., "The last step in the biosynthesis of aryl carotenoids in the cheese ripening bacteria Brevibacterium linens ATCC 9175 (Brevibacterium aurantiacum sp. nov.) involves a cytochrome P450-​dependent monooxygenase".
  • Ref.178 : Krubasik, P.; Sandmann, G., Molecular and General Genetics (2000), 263(3), 423-432., "A carotenogenic gene cluster from Brevibacterium linens with novel lycopene cyclase genes involved in the synthesis of aromatic carotenoids".
  • Ref.92 : Hirabayashi, Hiroki; Ishii, Takasada; Takaichi, Shinichi; Inoue, Kazuhito; Uehara, Kaku, Photochemistry and Photobiology (2004), 79(3), 280-285. , "The role of carotenoids in the photoadaptation of the brown-​colored sulfur bacterium Chlorobium phaeobacteroides".
  • Ref.93 : Psencik, Jakub; Ma, Ying-Zhong; Arellano, Juan B.; Garcia-Gil, Jesus; Holzwarth, Alfred R.; Gillbro, Tomas, Photosynthesis Research (2002), 71(1-2), 5-18., "Excitation energy transfer in chlorosomes of Chlorobium phaeobacteroides strain CL1401 and role of carotenoids".
  • Ref.95 : Miki, W.; Otaki, N.; Yokoyama, A.; Kusumi, T., Experientia (1996), 52(1), 93-6., "Possible origin of zeaxanthin in the marine sponge, Reniera japonica".
  • Ref.184 : Tsumaki, Tokuichi; Yamaguchi, Masaru; Tsumaki, Tasuichi, Nippon Kagaku Kaishi (1921-47) (1954), Pure Chem. Sect. 75, 297-300., "Pigments of marine animals. I. The pigments of a sponge Reniera japonica".
  • Ref.96 : Hertzberg, Sissel; Englert, Gerhard; Bergguist, Patricia; Liaaen-Jensen, Synnoeve, Bulletin des Societes Chimiques Belges (1986), 95(9-10), 801-14., "Animal carotenoids. Part 30. Carotenoids of the sponge Polymastia granulosa (Hadromerida)".
  • Ref.97 : Matsuno, Takao; Maoka, Takashi; Katagiri, Kiyoshi; Komori, Tadaaki, Nippon Suisan Gakkaishi (1984), 50(6), 1071-5., "A new carotenoid, isorenieradicistene from the sea sponge, Suberites sericeus".
  • Ref.98 : Tanaka, Yoshito; Soejima, Takumi; Katayama, Teruhisa, Nippon Suisan Gakkaishi (1978), 44(11), 1283-5., "Biochemical studies of the carotenoids in porifera. Distribution of the carotenoids in porifera".
  • Ref.99 : Buchecker, Richard; Eugster, Conrad Hans; Litchfield, Carter, Helvetica Chimica Acta (1977), 60(8), 2780-8., "Carotenoids from marine sponges (Porifera)​: isolation and structure of the seven main carotenoids from Agelas schmidtii".
  • Ref.100 : Parisi, G.; Pierantoni, R.; Porcelli, M., Marine Biology (Berlin, Germany) (1977), 41(2), 191-7., "Pigments of the Porifera: Demospongiae. I. Carotenoids of Axinella verrucosa".
  • Ref.101 : David, Hugo L., Applied Microbiology (1974), 28(4), 696-9., "Carotenoid pigments of Mycobacterium kansasii".
  • Ref.102 : McBeth, James W., Comparative Biochemistry and Physiology, Part B: Biochemistry & Molecular Biology (1972), 41(1), 55-68. , "Carotenoids from nudibranchs".
  • Ref.87 : Arcamone, Federico; Camerino, Bruno; Cotta, E.; Franceschi, Giovanni; Grein, Arpad; Penco, Sergio; Spalla, Celestino, Experientia (1969), 25(3), 241-2., "Carotenoids from Streptomyces mediolani".
  • Ref.88 : Bianchi, Maria L.; Grein, A.; Julita, P.; Marnati, Maria P.; Spalla, Celestino, Zeitschrift fuer Allgemeine Mikrobiologie (1970), 10(4), 237-44., "Streptomyces mediolani and its production of carotenoids".
  • Ref.103 : Hochmannova, J.; Kolmanova, A.; Malek, I., Folia Microbiologica (Prague, Czech Republic) (1968), 13(6), 505-9., "Comparison of pigments produced by several [genetically related] strains of Mycobacterium phlei".
  • Ref.148 : Schaeffer, Philippe; Adam, Pierre; Wehrung, Patrick; Albrecht, Pierre, Tetrahedron Letters (1997), 38(48), 8413-8416., "Novel aromatic carotenoid derivatives from sulfur photosynthetic bacteria in sediments".
  • Ref.94 : Abella, C. A.; Cristina, X. P.; Martinez, A.; Pibernat, I.; Vila, X., Archives of Microbiology (1998), 169(5), 452-459., "Two new motile phototrophic consortia: "Chlorochromatium lunatum" and "Pelochromatium selenoides".
  • Ref.369 : Buchecker, Richard; Eugster, Conrad Hans; Litchfield, Carter, Helvetica Chimica Acta, Volume60, Issue8, Pages2780-8, 1977, ISSN:0018-019X, "Carotenoids from marine sponges (Porifera):  isolation and structure of the seven main carotenoids from Agelas schmidtii".
  • Ref.491 : Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A., Biol Pharm Bull. 1995 Feb;18(2):227-33., PMID: 7742789, "Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters.".
  • CAS
    524-01-6
    Links to other DB
    KEGG COMPOUND: C15943
    KNApSAcK: C00022816
    LipidBank: VCA1042
    MassBank: CA000065
    ProCarDB: C1086

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