absinthin   Click here for help

GtoPdb Ligand ID: 12458

Synonyms: (+)-absinthin | absynthin
Comment: Absinthin is a naturaly occurring, bitter tasting compound that is present in Artemisia absinthium (Wormwood), and other Artemisia sp. plants.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 93.06
Molecular weight 496.64
XLogP 1.99
No. Lipinski's rules broken 0
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Canonical SMILES CC1=C[C@@H]2[C@H]3[C@H](C(=C4[C@@H]3[C@](C)(CC[C@H]5[C@H](C)C(=O)O[C@@H]54)O)C)[C@@]16[C@@H]2[C@](C)(CC[C@H]7[C@H](C)C(=O)O[C@@H]76)O
Isomeric SMILES C[C@H]1[C@@H]2CC[C@]([C@@H]3[C@H]4[C@H]5C=C([C@@]6([C@H]4C(=C3[C@H]2OC1=O)C)[C@@H]5[C@@](CC[C@@H]7[C@@H]6OC(=O)[C@H]7C)(C)O)C)(C)O
InChI InChI=1S/C30H40O6/c1-12-11-18-20-21(30(12)24(18)29(6,34)10-8-17-14(3)27(32)36-25(17)30)15(4)19-22(20)28(5,33)9-7-16-13(2)26(31)35-23(16)19/h11,13-14,16-18,20-25,33-34H,7-10H2,1-6H3/t13-,14-,16-,17-,18+,20-,21-,22-,23-,24-,25-,28-,29-,30+/m0/s1
1. Brockhoff A, Behrens M, Massarotti A, Appendino G, Meyerhof W. (2007)
Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium.
J Agric Food Chem, 55 (15): 6236-43. [PMID:17595105]
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]