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Entry
CA01064                                                            

Classification
Carotenoid Name
Picrocrocin
IUPAC name (3R)-3-(beta-D-Glucopyranosyloxy)-7-apo-beta-caroten-7-al
Formula
C16H26O7
Molecular Weight 
330.368 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity (Ref.457).
  • Bitter taste (Ref.458).
  • Number of
    conjugated double bonds 
    2 including one aldehyde (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one aldehyde (2 in total)
    Isomers 
    InChI
    InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1
    InChIKey
    WMHJCSAICLADIN-WYWSWGBSSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](O[C@@H]2CC(=C(C(C2)(C)C)C=O)C)[C@@H]([C@H]([C@@H]1O)O)O
    XLogP
    -0.207
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    0
    Complexity of molecule
    0.265
    Number of heavy atoms
    23
    TPSA
    (Topological Polar Surface Area) 
    116.450 Å2
    Source organisms
    Crocus sativus (Ref.454, Ref.455) - Land plant: saffron crocus
    References
  • Ref.454 : Sarah Frusciantea,b, Gianfranco Direttoa, Mark Brunoc, Paola Ferrantea, Marco Pietrellaa, Alfonso Prado-Cabrerod, Angela Rubio-Moragae, Peter Beyerc, Lourdes Gomez-Gomeze, Salim Al-Babilic,d, and Giovanni Giulianoa, PNAS, August 19, 2014, pp.12246–12251, vol. 111, no. 33, "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis".
  • Ref.455 : H. Pfander, and H. Schurternberger, Phytochemistry, vol.21, No.5, pp.1039-1042, 1982, "Biosynthesis of C20-carotenoids in Crocus sativus".
  • Ref.457 : Julio Escribanoa, Gonzalo-Luis Alonsob, Miguel Coca-Pradosc, José-Antonio Fernández, Cancer Letters, Volume 100, Issues 1–2, 27 February 1996, Pages 23–30, "Crovin, safranal, and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cell in vitro".
  • Ref.458 : R. Srivastava, H. Ahmed, R. K. Dixit, Dharamveer, and S. A. Saraf, Pharmacogn Rev. 2010 Jul-Dec; 4(8): 200–208., doi: 10.4103/0973-7847.70919, "Crocus sativus L.: A comprehensive review".
  • CAS

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