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Entry
CA00893                                                            

Classification
Carotenoid Name
Norbixin
IUPAC name (9Z)-6,6'-Diapocarotene-6,6'-dioic acid
Formula
C24H28O4
Molecular Weight 
380.464 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Yellow food coloring (Ref.468).
  • Antimicrobial activity (Ref.480).
  • Anticarcinogenic activity - inhibit tyrosinase activity in melanoma cells in vitro (Ref.481).
  • Number of
    conjugated double bonds 
    11 including two carboxylic acids (11 in total)
    Number of
    conjugated multiple bonds 
    11 including two carboxylic acids (11 in total)
    Isomers 
    InChI
    InChI=1S/C24H28O4/c1-19(11-7-13-21(3)15-17-23(25)26)9-5-6-10-20(2)12-8-14-22(4)16-18-24(27)28/h5-18H,1-4H3,(H,25,26)(H,27,28)/b6-5+,11-7+,12-8+,17-15+,18-16+,19-9+,20-10+,21-13-,22-14+
    InChIKey
    ZVKOASAVGLETCT-LRRSNBNMSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C(=O)O)/C)/C)/C=C/C=C(\C=C\C(=O)O)/C
    XLogP
    6.282
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.000
    Number of heavy atoms
    28
    TPSA
    (Topological Polar Surface Area) 
    74.600 Å2
    Source organisms
    Bixa orellana (Ref.140) - Land plant: Bixaceae
    References
  • Ref.140 : Bouvier Florence; Dogbo Odette; Camara Bilal, Science (New York, N.Y.) (2003), 300(5628), 2089-91., "Biosynthesis of the food and cosmetic plant pigment bixin (annatto)".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • Ref.480 : Galindo-Cuspinera V, Rankin SA, J Agric Food Chem. 2005 Apr 6;53(7):2524-9., "Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts.".
  • Ref.481 : Anantharaman A, Hemachandran H, Priya RR, Sankari M, Gopalakrishnan M, Palanisami N, Siva R., J Biosci Bioeng. 2015 Jul 14. pii: S1389-1723(15)00200-5. doi: 10.1016/j.jbiosc.2015.05.007., PMID: 26187443, "Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies".
  • CAS
    542-40-5
    Links to other DB
    KNApSAcK: C00003782
    LipidBank: VCA1127

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