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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00337
  • Product: CR00099,  CR00435
    • Pathway
  • Pathway: CB000108
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Bixa orellana (Ref.140, Ref.764) - Land plant: Bixaceae (Streptophyta - 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.764: A. Z. MERCADANTE, A. STECK, D. RODRIGUEZ-AMAYA,t H. PFANDER and G. BRITTON, Phytochemistry, Vol. 41, No. 4, pp. 1201 1203, 1996, “ISOLATION OF METHYL 9'Z-APO-6'-LYCOPENOATE FROM BIXA ORELLANA”.
  • 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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