compound 3 [PMID: 24900526]   

GtoPdb Ligand ID: 7868

Compound class: Synthetic organic
Comment: This is an MMP12-specific peptide sequence with the active inhibitor released upon enzyme cleavage as a three-step conversion predrug (this entry) > prodrug compound 5 [PMID: 24900526] > drug compound 1 [PMID: 24900526] [1]
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 23
Hydrogen bond donors 8
Rotatable bonds 36
Topological polar surface area 355.56
Molecular weight 1076.45
XLogP 3.61
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CCC(C(=O)NC(C(=O)NC(C(=O)N)C)CCC(=O)O)NC(=O)C(NC(=O)CN(S(=O)(=O)c1ccc(cc1)c1ccccc1)C(=O)C(NC(=O)C1CCCN1C(=O)OCc1ccccc1)CC(C)C)CC(C)C
Isomeric SMILES OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)C)CCC(=O)O)NC(=O)[C@@H](NC(=O)CN(S(=O)(=O)c1ccc(cc1)c1ccccc1)C(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1)CC(C)C)CC(C)C
InChI InChI=1S/C52H68N8O15S/c1-31(2)27-40(49(69)57-39(23-25-45(64)65)48(68)56-38(22-24-44(62)63)47(67)54-33(5)46(53)66)55-43(61)29-60(76(73,74)37-20-18-36(19-21-37)35-15-10-7-11-16-35)51(71)41(28-32(3)4)58-50(70)42-17-12-26-59(42)52(72)75-30-34-13-8-6-9-14-34/h6-11,13-16,18-21,31-33,38-42H,12,17,22-30H2,1-5H3,(H2,53,66)(H,54,67)(H,55,61)(H,56,68)(H,57,69)(H,58,70)(H,62,63)(H,64,65)/t33-,38-,39-,40-,41-,42-/m0/s1
InChI Key XGNIOZCAZTWXMZ-WCHFFXHOSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(4S)-5-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-4-[[(2S)-4-carboxy-2-[[(2S)-4-methyl-2-[[2-[[(2S)-4-methyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]pentanoyl]-(4-phenylphenyl)sulfonylamino]acetyl]amino]pentanoyl]amino]butanoyl]amino]-5-oxopentanoic acid
Database Links
ChEMBL Ligand CHEMBL2205657
GtoPdb PubChem SID 223366198
PubChem CID 66560533
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