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Entry
CA00848                                                            

Classification
Carotenoid Name
β-Apo-13-carotenone;
13-Apo-β-carotenone;
beta-Apo-13-carotenone;
13-Apo-beta-carotenone
IUPAC name 13-Apo-beta-caroten-13-one
Formula
C18H26O
Molecular Weight 
258.388 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
5 including one ketone (5 in total)
Number of
conjugated multiple bonds 
5 including one ketone (5 in total)
Isomers 
InChI
InChI=1S/C18H26O/c1-14(8-6-10-16(3)19)11-12-17-15(2)9-7-13-18(17,4)5/h6,8,10-12H,7,9,13H2,1-5H3/b10-6+,12-11+,14-8+
InChIKey
UBTNVRPIHJRBCI-LUXGDSJYSA-N
Canonical SMILES
C/C(=C\C=C\C(=O)C)/C=C/C1=C(C)CCCC1(C)C
XLogP
5.430
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.133
Number of heavy atoms
19
TPSA
(Topological Polar Surface Area) 
17.070 Å2
Source organisms
Novosphingobium aromaticivorans (Ref.166) - Alphaproteobacteria: Sphingomonadaceae
Cucumis melo Inodorus Group (Ref.392) - Land plant: orange-fleshed muskmelon "honeydew"
Mycobacterium tuberculosis (Ref.557) - Actinobacteria
Arabidopsis thaliana (Ref.554) - Land plant: thale-cress, a model organism
References
  • Ref.166 : YS Kim, ES Seo, DK Oh - Biotechnology letters, October 2012, Volume 34, Issue 10, pp 1851-1856, "Characterization of an apo-carotenoid 13, 14-dioxygenase from Novosphingobium aromaticivorans that converts β-apo-8′-carotenal to β-apo-13-carotenone".
  • Ref.392 : Fleshman, Matthew K.; Lester, Gene E.; Riedl, Ken M.; Kopec, Rachel E.; Narayanasamy, Sureshbabu; Curley, Robert W.; Schwartz, Steven J.; Harrison, Earl H., Journal of Agricultural and Food Chemistry (2011), 59(9), 4448-4454., "Carotene and Novel Apocarotenoid Concentrations in Orange-Fleshed Cucumis melo Melons: Determinations of β-Carotene Bioaccessibility and Bioavailability".
  • Ref.557 : Daniel Scherzinger, Erdmann Scheffer, Cornelia Bar, Hansgeorg Ernst and Salim Al-Babili, FEBS J. 2010 Nov;277(22):4662-73. doi: 10.1111/j.1742-4658.2010.07873.x. Epub 2010 Oct 4."The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids" .
  • Ref.554 : Daniela S. Floss and Michael H. Walter, Plant Signaling & Behavior 4:3, 172-175; March 2009, "Role of carotenoid cleavage dioxygenase 1 (CCD1) in apocarotenoid biogenesis revisited".
  • CAS
    17974-57-1
    Links to other DB
    KEGG COMPOUND: C20696
    ProCarDB: C0245

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