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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      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Bright pink color (Ref.430).
  • Higher antioxidant capacities than all-E-isomer (Ref.780).
    • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
  • Cis/trans isomer: CA00043, CA01130, CA01131, CA01132
    • InChI

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00391
  • Product: CR00448,  CR00012
    • Pathway
  • Pathway: CB000004
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Oryza sativa L. var. Nipponbare (Ref.128) - Land plant: rice (Streptophyta - Poaceae)
    Brassica rapa (Ref.122) - Land plant: field mustard (Streptophyta - Brassiceae)
    Solanum lycopersicum (Ref.123) - Land plant: Solanaceae: tomato, same as Lycopersicon esculentum (Streptophyta - Solanaceae)
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit (Streptophyta - Passifloraceae)
    Rosa rubiginosa (Ref.127) - Land plant: Rosaceae: rose (Streptophyta - Rosaceae)
    Rosa dumalis hybrid (Ref.127) - Land plant: Rosaceae: rose (Streptophyta - Rosaceae)
    Rosa dumalis (Ref.127) - Land plant: Rosaceae: rose (Streptophyta - Rosaceae)
    Carica papaya (Ref.126) - Land plant: papaya (Streptophyta - Caricaceae)
    Citrullus vulgaris (Ref.180) - Land plant: watermelon (Streptophyta - Cucurbitaceae)
    Calendula officinalis (Ref.430) - Land plant: common marigold (Streptophyta - Asteraceae)
    Elaeis spp. (Ref.431) - Land plant: palm oil (Streptophyta - Arecaceae)
    References
  • 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.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".
  • Ref.129: Sandra Regina da SILVA, Adriana Z. MERCADANTE, Cienc. Tecnol. Aliment., Campinas (Campinas, Brazil) (2002), 22(3), 254-258., "Carotenoid composition of fresh yellow passion fruit (Passiflora edulis flavicarpa)".
  • Ref.780: Masaki Honda, Ikumi Horiuchi, Hayato Hiramatsu, Yoshinori Inoue, Chitoshi Kitamura, Tetsuya Fukaya and Munenori Takehara, Eur. J. Lipid Sci. Technol. 2016, 118, 1588–1592, “Vegetable oil-mediated thermal isomerization of (all-E)-lycopene: Facile and efficient production of Z-isomers”.
    • CAS
    2361-24-2
    Links to other DB
    KEGG COMPOUND: C15858
    KNApSAcK: C00000909

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