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Entry
CA00044                                                            

Classification
Carotenoid Name
Prolycopene;
(7Z,9Z,7'Z,9'Z)-Lycopene;
7,9,9',7'-tetra-cis-Lycopene;
7,9,7',9'-tetracis-Lycopene;
Neolycopene;
Neolycopene A
IUPAC name (7Z,9Z,7'Z,9'Z)-psi,psi-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Bright pink color (Ref.430).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
  • Cis/trans isomer: CA00043, CA01130, CA01131, CA01132
  • InChI
    InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17-,32-18-,35-21+,36-22+,37-27+,38-28+,39-29-,40-30-
    InChIKey
    OAIJSZIZWZSQBC-BYUNHUQQSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(/C=C\C=C(\CCC=C(C)C)/C)\C)/C)/C=C/C=C(\C=C/C=C(/CCC=C(C)C)\C)/C
    XLogP
    14.586
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Synechocystis sp. PCC 6803 (Ref.130) - Cyanobacteria: freshwater cyanobacteria
    Pantoea ananatis (Ref.105) - Gammaproteobacteria: plant pathogenic bacteria
    Brassica rapa (Ref.122) - Land plant: field mustard
    Solanum lycopersicum (Ref.123) - Land plant: Solanaceae: tomato
    Citrullus vulgaris (Ref.180) - Land plant: watermelon
    Passiflora edulis (Ref.125, Ref.187) - Land plant: yellow passion fruit
    Carica papaya (Ref.126) - Land plant: papaya
    Rosa rubiginosa (Ref.127) - Land plant: Rosaceae: rose
    Rosa dumalis (Ref.127) - Land plant: Rosaceae: rose
    Rosa dumalis hybrid (Ref.127) - Land plant: Rosaceae: rose
    Oryza sativa L. var. Nipponbare (Ref.128) - Land plant: rice
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Elaeis spp. (Ref.431) - Land plant: palm oil
    References
  • Ref.130 : Breitenbach, Jurgen; Vioque, Agustin; Sandmann, Gerhard, Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2001), 56(9/10), 915-917., "Gene sll0033 from Synechocystis 6803 encodes a carotene isomerase involved in the biosynthesis of all-​E lycopene".
  • Ref.105 : Schaub, Patrick; Yu, Qiuju; Gemmecker, Sandra; Poussin-Courmontagne, Pierre; Mailliot, Justine; Ghisla, Sandro; Al-Babili, Salim; Cavarelli, Jean; Beyer, Peter, PLoS One (2012), 7(6), e39550., "On the structure and function of the phytoene desaturase CRTI from Pantoea ananatis, a membrane-​peripheral and FAD-​dependent oxidase​/isomerase".
  • Ref.122 : Li, Pei-rong; Zhang, Shu-jiang; Zhang, Shi-fan; Li, Fei; Zhang, Hui; Liu, Xin-yan; Wu, Jian; Wang, Xiao-wu; Sun, Ri-fei, Yuanyi Xuebao (2014), 41(3), 469-478., "Analysis of carotenoids pigments and orange inner leaf gene in Chinese cabbage (Brassica rapa)".
  • Ref.123 : Fantini, Elio; Falcone, Giulia; Frusciante, Sarah; Giliberto, Leonardo; Giuliano, Giovanni, Plant Physiology (2013), 163(2), 986-998., "Dissection of tomato lycopene biosynthesis through virus-​induced gene silencing".
  • Ref.180 : Liu, Cuihua; Zhang, Hongyan; Dai, Zhaoyi; Liu, Xi; Liu, Yue; Deng, Xiuxin; Chen, Feng; Xu, Juan, Food Science and Biotechnology (2012), 21(2), 531-541., "Volatile chemical and carotenoid profiles in watermelons [Citrullus vulgaris (Thunb.) Schrad (Cucurbitaceae)​] with different flesh colors".
  • Ref.125 : Wondracek, Daniele Cristina; Vieira, Roberto Fontes; da Silva, Dijalma Barbosa; Agostini-Costa, Tania da Silveira; Sano, Sueli Matiko; Faleiro, Fabio Gelape, Quimica Nova (2012), 35(1), 180-184., "Saponification influence in carotenoid determination in cerrado passion fruit".
  • Ref.187 : Mercadante, A. Z.; Britton, G.; Rodriguez-Amaya, D. B., Journal of Agricultural and Food Chemistry (1998), 46(10), 4102-4106., "Carotenoids from Yellow Passion Fruit (Passiflora edulis)".
  • Ref.126 : Barreto, Gisela P. M.; Fabi, Joao P.; De Rosso, Veridiana V.; Cordenunsi, Beatriz R.; Lajolo, Franco M.; do Nascimento, Joao R. O.; Mercadante, Adriana Z., Journal of Food Composition and Analysis (2011), 24(4-5), 620-624., "Influence of ethylene on carotenoid biosynthesis during papaya postharvesting ripening".
  • Ref.127 : Andersson, Staffan C.; Rumpunen, Kimmo; Johansson, Eva; Olsson, Marie E., Food Chemistry (2011), 128(3), 689-696., "Carotenoid content and composition in rose hips (Rosa spp.) during ripening, determination of suitable maturity marker and implications for health promoting food products".
  • Ref.128 : Chai, Chenglin; Fang, Jun; Liu, Yang; Tong, Hongning; Gong, Yanqing; Wang, Yiqin; Liu, Min; Wang, Youping; Qian, Qian; Cheng, Zhukuan; et al, Plant Molecular Biology (2011), 75(3), 211-221., "ZEBRA2, encoding a carotenoid isomerase, is involved in photoprotection in rice".
  • Ref.129 : da Silva, Sandra Regina; Mercadante, Adriana Z., Ciencia e Tecnologia de Alimentos (Campinas, Brazil) (2002), 22(3), 254-258., "Carotenoid composition of fresh yellow passion fruit (Passiflora edulis flavicarpa)".
  • Ref.430 : T. W. GOODWIN, Biochem J. 1954 Sep;58(1):90-4., "Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.".
  • Ref.431 : R. F. Hunter and R. M. Krakenberger, Biochem Jv.40(4); 1946PMC1258385, "Palm-oil carotenoids".
  • CAS
    2361-24-2
    Links to other DB
    KEGG COMPOUND: C15858
    KNApSAcK: C00000909

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