Artocarpin
Basic information
- CAS
7608-44-8- Standard SMILES
COc1cc2oc(-c3ccc(O)cc3O)c(CC=C(C)C)c(=O)c2c(O)c1/C=C/C(C)C- InChIKey
KRGDFVQWQJIMEK-RMKNXTFCSA-N- Molecular formula
- C26H28O6
- Average molar mass
- 436.5 g/mol
- Monoisotopic mass
- 436.18858861
Overview
Artocarpin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 2', and 4', a methoxy group at position 7, a prenyl group at position 3 and a (1E)-3-methylbut-1-enyl group at position 6. Isolated from Artocarpus heterophyllus and Artocarpus integrifolia, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a monomethoxyflavone and a trihydroxyflavone.
Names & identifiers
- Preferred name
- Artocarpin
- IUPAC
- 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(E)-3-methylbut-1-enyl]-3-(3-methylbut-2-enyl)chromen-4-one
- English name
- artocarpin
- Molecular formula
- C26H28O6
- Molecular weight
- 436.5
Names & synonyms
ARTOCARPIN2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(E)-3-methylbut-1-enyl]-3-(3-methylbut-2-enyl)chromen-4-oneCHEBI:654392-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-((1E)-3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-((E)-3-methylbut-1-enyl)-3-(3-methylbut-2-enyl)chromen-4-oneRefChem:10772477608-44-8NSC241010CHEMBL72617Artocarpin LectinArtocaprin
Show more names
NSC 2410102',4',5-Trihydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)flavone2',4',5-Trihydroxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)-7-methoxyflavone2-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methyl-1-buten-1-yl]-3-(3-methyl-2-buten-1-yl)-4H-chromen-4-one4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methyl-1-buten-1-yl)-3-(3-methyl-2-buten-1-yl)-
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 96.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 762
Experimental & physicochemical properties
Melting Point174 - 175 °C
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 667.1 · 667.1±55.0 °C(Predicted)
- Density
- 1.242 · 1.242±0.06 g/cm3(Predicted)
- pka
- 6.38 · 6.38±0.40(Predicted)
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesArtocarpin can be used in combination with other agents for treating various diseases. It can also be used to activate the Nrf2-mediated defense system, SAR, and inhibit intracellular oxidative insults.
Additional notes
DefinitionChEBI: A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 2', and 4', a methoxy group at position 7, a prenyl group at position 3 and a (1E)-3-methylbut-1-enyl group at position 6. Isolated from Artocarpus het rophyllus and Artocarpus integrifolia, it exhibits antineoplastic activity.
Related reactions
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Compound notes
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