compound 3 [PMID: 24900526]   Click here for help

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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(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 Click here for help
ChEMBL Ligand CHEMBL2205657
GtoPdb PubChem SID 223366198
PubChem CID 66560533
Search Google for chemical match using the InChIKey XGNIOZCAZTWXMZ-WCHFFXHOSA-N
Search Google for chemicals with the same backbone XGNIOZCAZTWXMZ
UniChem Compound Search for chemical match using the InChIKey XGNIOZCAZTWXMZ-WCHFFXHOSA-N
UniChem Connectivity Search for chemical match using the InChIKey XGNIOZCAZTWXMZ-WCHFFXHOSA-N