grassystatin A   

GtoPdb Ligand ID: 8674

Comment: Grassystatin A is a bioactive compound isolated from marine cyanobacteria. It is a potent and selective inhibitor of cathepsin E [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 25
Hydrogen bond donors 8
Rotatable bonds 43
Topological polar surface area 351.81
Molecular weight 1173.69
XLogP 2.42
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C1CCCN1C(=O)C(N(C(=O)C(NC(=O)C(C(O)C)NC(=O)CC(C(NC(=O)C(NC(=O)C(NC(=O)C(C(C)C)OC(=O)C(C(C)C)OC(=O)C(N(C)C)C(C)C)CC(C)C)CC(=O)N)CC(C)C)O)C)C)Cc1ccccc1
Isomeric SMILES COC(=O)[C@@H]1CCCN1C(=O)[C@H](N(C(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)C[C@@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)OC(=O)[C@@H](N(C)C)C(C)C)CC(C)C)CC(=O)N)CC(C)C)O)C)C)Cc1ccccc1
InChI InChI=1S/C58H95N9O16/c1-30(2)25-38(43(69)29-45(71)64-46(36(12)68)52(74)60-35(11)54(76)66(15)42(27-37-21-18-17-19-22-37)55(77)67-24-20-23-41(67)56(78)81-16)61-51(73)40(28-44(59)70)62-50(72)39(26-31(3)4)63-53(75)48(33(7)8)82-58(80)49(34(9)10)83-57(79)47(32(5)6)65(13)14/h17-19,21-22,30-36,38-43,46-49,68-69H,20,23-29H2,1-16H3,(H2,59,70)(H,60,74)(H,61,73)(H,62,72)(H,63,75)(H,64,71)/t35-,36+,38-,39-,40-,41-,42+,43-,46-,47-,48+,49-/m0/s1
InChI Key JZYWSTGTBRHGTL-BIXXXADNSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S,3R)-2-[[(3S,4S)-4-[[(2S)-4-amino-2-[[(2S)-2-[[(2R)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanoyl]oxy-3-methylbutanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
Database Links
ChEMBL Ligand CHEMBL567893
GtoPdb PubChem SID 252166874
PubChem CID 44255320
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