compound 5 [PMID: 10869194]   

GtoPdb Ligand ID: 8843

Comment: Compound 5 is a pentacyclic triterpene ester isolated from Uncaria rhynchophylla, a plant used in traditional medicine by various indigenous cultures. Compound 5 is reported to inhibit phospholipase C-gamma 1 (PLCG1) [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 94.83
Molecular weight 602.4
XLogP 9.49
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(CC12CCC3(C(C1=CCC1C2(C)CCC2C1(C)CCC(C2(C)C)O)C(C)C(CC3)C)C(=O)O)C=Cc1ccc(cc1)O
Isomeric SMILES O=C(C[C@@]12CC[C@@]3([C@H](C1=CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)[C@@H](C)[C@@H](CC3)C)C(=O)O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C39H54O5/c1-24-15-20-38(34(43)44)21-22-39(23-28(41)12-9-26-7-10-27(40)11-8-26)29(33(38)25(24)2)13-14-31-36(5)18-17-32(42)35(3,4)30(36)16-19-37(31,39)6/h7-13,24-25,30-33,40,42H,14-23H2,1-6H3,(H,43,44)/b12-9+/t24-,25+,30+,31-,32+,33+,36+,37-,38+,39+/m1/s1
InChI Key NOTLGMDYQMIWNO-ZBFFZJPBSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[(E)-4-(4-hydroxyphenyl)-2-oxobut-3-enyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Database Links
ChEMBL Ligand CHEMBL503874
GtoPdb PubChem SID 252827500
PubChem CID 44583698
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