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Entry
CA00808                                                            

Classification
Carotenoid Name
β-Apo-14'-carotenal;
beta-Apo-14'-carotenal;
All-trans-C-22;
14'-apo-β-Carotenal;
14'-apo-beta-Carotenal
IUPAC name 14'-Apo-beta-caroten-14'-al
Formula
C22H30O
Molecular Weight 
310.46 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
7 including one aldehyde (7 in total)
Number of
conjugated multiple bonds 
7 including one aldehyde (7 in total)
Isomers 
InChI
InChI=1S/C22H30O/c1-18(10-6-7-17-23)11-8-12-19(2)14-15-21-20(3)13-9-16-22(21,4)5/h6-8,10-12,14-15,17H,9,13,16H2,1-5H3/b7-6+,11-8+,15-14+,18-10+,19-12+
InChIKey
NGISIFNAHMKVQR-SSRYJDFZSA-N
Canonical SMILES
O=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
XLogP
7.029
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.113
Number of heavy atoms
23
TPSA
(Topological Polar Surface Area) 
17.070 Å2
Source organisms
Mycobacterium tuberculosis (Ref.557) - Actinobacteria
Cucumis melo Inodorus Group (Ref.392) - Land plant: orange-fleshed muskmelon "honeydew"
Galleria mellonella (Ref.558) - Insect: greater wax moth
References
  • 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.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.558 : Vitus Oberhausera, Olaf Voolstraa, Annette Bangerta, Johannes von Lintigb, and Klaus Vogt, Proc Natl Acad Sci U S A. 2008 Dec 2;105(48):19000-5. doi: 10.1073/pnas.0807805105. Epub 2008 Nov 19., "NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide.".
  • CAS
    6985-27-9
    Links to other DB
    KEGG COMPOUND: C06734

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