theaflavin   Click here for help

GtoPdb Ligand ID: 12464

Synonyms: (-)-Theaflavin | Theaflavine
Compound class: Natural product
Comment: Theaflavin is a polyphenol compound that is present in black tea.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 9
Rotatable bonds 2
Topological polar surface area 217.6
Molecular weight 564.49
XLogP 0.61
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES C1=C(C=C(C(=O)C2=C1C(=CC(=C2O)O)[C@@H]3[C@@H](CC4=C(C=C(C=C4O)O)O3)O)O)[C@@H]5[C@@H](CC6=C(C=C(C=C6O)O)O5)O
Isomeric SMILES C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC4=C(C(=C(C=C4[C@@H]5[C@@H](CC6=C(C=C(C=C6O5)O)O)O)O)O)C(=O)C(=C3)O)O
InChI InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1
InChI Key IPMYMEWFZKHGAX-ZKSIBHASSA-N
References
1. Yamazaki T, Sagisaka M, Ikeda R, Nakamura T, Matsuda N, Ishii T, Nakayama T, Watanabe T. (2014)
The human bitter taste receptor hTAS2R39 is the primary receptor for the bitterness of theaflavins.
Biosci Biotechnol Biochem, 78 (10): 1753-6. [PMID:25273142]