amarogentin   Click here for help

GtoPdb Ligand ID: 12459

Comment: Amarogentin is a bitter tasting naturally occurring plant compound.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 6
Rotatable bonds 8
Topological polar surface area 201.67
Molecular weight 586.54
XLogP 1.25
No. Lipinski's rules broken 3
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Canonical SMILES C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)OC(=O)C4=C(C=C(C=C4C5=CC(=CC=C5)O)O)O
Isomeric SMILES C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O
InChI InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
1. Behrens M, Brockhoff A, Batram C, Kuhn C, Appendino G, Meyerhof W. (2009)
The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin.
J Agric Food Chem, 57 (21): 9860-6. [PMID:19817411]
2. Meyerhof W, Batram C, Kuhn C, Brockhoff A, Chudoba E, Bufe B, Appendino G, Behrens M. (2010)
The molecular receptive ranges of human TAS2R bitter taste receptors.
Chem Senses, 35 (2): 157-70. [PMID:20022913]
3. Roudnitzky N, Behrens M, Engel A, Kohl S, Thalmann S, Hübner S, Lossow K, Wooding SP, Meyerhof W. (2015)
Receptor Polymorphism and Genomic Structure Interact to Shape Bitter Taste Perception.
PLoS Genet, 11 (9): e1005530. [PMID:26406243]