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Entry |
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Classification |
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Carotenoid Name
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Megastigma-4,6,8-trien-3-one;
Megastigmatrienone;
Tabanone;
Megastigma-4,6Z,8E-trien-3-one;
4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1- one;
(E,E/E,Z)-tobacco cyclohexenone
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IUPAC name |
10-Apo-6,7,8,9-tetradehydro-7,8,9,10-tetradehydro-epsilon-caroten-3-one
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Formula |
C13H18O
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Molecular Weight |
190.274 g/mol
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Structure |
Search similar carotenoids
Mol file
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Carotenoid DB Fingerprints |
Predict biological activities of this carotenoid
10-apo, 6,7--H, 8,9--H, 7,8+H, 9,10+H, 3=O, epsilon
( Help )
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Biological functions/Properties |
A key flavor compound in wine and tobacco (Ref.624, Ref.623).
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Number of
conjugated double bonds |
4 including one ketone
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Number of
conjugated multiple bonds |
4 including one ketone
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Isomers |
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InChI |
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InChIKey |
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Canonical SMILES |
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XLogP |
3.325
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Hydrogen Bond donors
(Lipinski's definition) |
0
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Hydrogen Bond Acceptors
(Lipinski's definition) |
1
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| LipinskiFailures |
0
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| Complexity of molecule |
0.188
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| Number of heavy atoms |
14
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TPSA
(Topological Polar Surface Area) |
17.070 Å2
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Reaction |
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Pathway |
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Major carotenoid information |
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Minor carotenoid information |
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Source organisms |
Nicotiana tabacum (Ref.623) - Land plant: common tobacco (Streptophyta - Solanaceae)Vitis sp. (Ref.623) - Land plant: grapevine (Streptophyta - Vitaceae)
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References |
Ref.623: Peter Winterhalter and Russell Rouseff, ”Carotenoid-Derived Aroma Compounds: An Introduction”, ACS Symposium Series; American Chemical Society: Washington, DC, 2001., doi: 10.1021/bk-2002-0802.ch001.
Ref.624: David Slaghenaufi, Marie-Claire Perello, Stéphanie Marchand-Marion, Sophie Temperea, Gilles de Revel, "Quantitative solid phase microextraction – Gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine", Analytica Chimica Acta, Volume 813, 27 February 2014, Pages 63–69.
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CAS |
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Links to other DB |
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