grandinin   Click here for help

GtoPdb Ligand ID: 12436

Comment: Grandinin is an ellagitannin compound that is present in leaves from the Melaleuca quinquenervia tree, and in the bark of oak trees (Quercus sp.). In humans it is detected as a bitter taste via its interaction with the bitter taste receptor TAS2R7 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 30
Hydrogen bond donors 19
Rotatable bonds 2
Topological polar surface area 525.1
Molecular weight 1066.75
XLogP 2.73
No. Lipinski's rules broken 3
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Canonical SMILES C1=C(C(=C(C2=C1C(=O)OCC3C(C4C5[C@@H](C6=C(C(=C(C(=C6O)O)O)C7=C(C(=C(C(=C7C(=O)O4)C8=C(C=C(C(=C8O)O)O)C(=O)O3)O)O)O)C(=O)O5)C9([C@@H]([C@@H](C(CO)O9)O)O)O)OC(=O)C%10=C2C(=C(C(=C%10)O)O)O)O)O)O
Isomeric SMILES C1C2C(C3C4[C@@H](C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8([C@@H]([C@@H](C(O8)CO)O)O)O)OC(=O)C9=CC(=C(C(=C9C%10=C(C(=C(C=C%10C(=O)O1)O)O)O)O)O)O
InChI InChI=1S/C46H34O30/c47-4-12-27(54)40(64)46(70,76-12)23-22-21-19(33(60)36(63)34(22)61)18-20-17(31(58)35(62)32(18)59)16-8(3-11(50)26(53)30(16)57)42(66)72-13-5-71-41(65)6-1-9(48)24(51)28(55)14(6)15-7(2-10(49)25(52)29(15)56)43(67)73-37(13)39(75-44(20)68)38(23)74-45(21)69/h1-3,12-13,23,27,37-40,47-64,70H,4-5H2/t12?,13?,23-,27-,37?,38?,39?,40-,46?/m1/s1
Classification Click here for help
Compound class Natural product or derivative
Database Links Click here for help
Specialist databases
GPCRdb Ligand grandinin
Other databases
CAS Registry No. 115166-32-0 (source: PubChem)
GtoPdb PubChem SID 479821226
PubChem CID 492392
Search Google for chemical match using the InChIKey GCEXRPOQEVIITL-XJDSPLDHSA-N
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UniChem Compound Search for chemical match using the InChIKey GCEXRPOQEVIITL-XJDSPLDHSA-N
UniChem Connectivity Search for chemical match using the InChIKey GCEXRPOQEVIITL-XJDSPLDHSA-N