FR900359   

GtoPdb Ligand ID: 9336

Compound class: Synthetic organic
Comment: FR900359 from the plant Ardisia crenata is a specific inhibitor of Gq and an analogue of YM-254890. A recent report describes the total synthesis of FR900359 and analogues with SAR [1]. Note that structures with assay results are indexed in the Nature Chemistry paper as PubChem substances.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 22
Hydrogen bond donors 5
Rotatable bonds 17
Topological polar surface area 285.69
Molecular weight 1001.53
XLogP 2.98
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCC(=O)NC(C(C(C)C)O)C(=O)OC(C1NC(=O)C(C)N(C)C(=O)C(C)NC(=O)C(=C)N(C)C(=O)C(OC(=O)C(C(OC(=O)C(N(C1=O)C)C(OC)C)C(C)C)NC(=O)C)Cc1ccccc1)C(C)C
Isomeric SMILES CCC(=O)N[C@@H]([C@@H](C(C)C)O)C(=O)O[C@@H]([C@@H]1NC(=O)[C@H](C)N(C)C(=O)[C@H](C)NC(=O)C(=C)N(C)C(=O)[C@H](OC(=O)[C@H]([C@H](OC(=O)[C@@H](N(C1=O)C)[C@H](OC)C)C(C)C)NC(=O)C)Cc1ccccc1)C(C)C
InChI InChI=1S/C49H75N7O15/c1-17-34(58)52-35(39(59)24(2)3)47(65)70-40(25(4)5)36-46(64)56(15)38(30(11)68-16)49(67)71-41(26(6)7)37(51-31(12)57)48(66)69-33(23-32-21-19-18-20-22-32)45(63)55(14)28(9)42(60)50-27(8)44(62)54(13)29(10)43(61)53-36/h18-22,24-27,29-30,33,35-41,59H,9,17,23H2,1-8,10-16H3,(H,50,60)(H,51,57)(H,52,58)(H,53,61)/t27-,29-,30+,33+,35-,36-,37-,38-,39+,40+,41+/m0/s1
InChI Key IMXKHFILKMPFGB-ZWYWTTNJSA-N
Classification
Compound class Synthetic organic
IUPAC Name
[(1R)-1-[(3S,6S,9S,12S,18R,21S,22R)-21-acetamido-18-benzyl-3-[(1R)-1-methoxyethyl]-4,9,10,12,16-pentamethyl-15-methylidene-2,5,8,11,14,17,20-heptaoxo-22-propan-2-yl-1,19-dioxa-4,7,10,13,16-pentazacyclodocos-6-yl]-2-methylpropyl] (2S,3R)-3-hydroxy-4-methyl-2-(propanoylamino)pentanoate
Database Links
CAS Registry No. 107530-18-7 (source: PubChem)
GtoPdb PubChem SID 318164855
PubChem CID 14101198
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