MLN-3897   Click here for help

GtoPdb Ligand ID: 10750

Synonyms: AVE-9897 | AVE9897 | MLN3897
Compound class: Synthetic organic
Comment: MLN-3897 is a selective oral, small‐molecule receptor antagonist of CCR1 [1] and clinical lead that was developed for immunomodulatory potential and as a chemokine signalling inhibitor to reduce multiple myeloma (MM)-related osteolytic bone disease (blocking CCL3-CCR1-mediated signalling inhibits osteoclast formation and MM cell migration and survival) [3]. We show the chemical structure here without specified stereochemistry, as depicted in the 2016 article by Pusalkar et al. [1]. A stereo-specified enantiomer is claimed as (abs)-50 in MIllenium Pharmaceuticals' patent US20090286823 [4]. As there has been no formal disclosure of the name-to-structure, we show the 'flat' structure in good faith.

Analysis presented in a bioRxiv preprint (not peer reviewed) suggests that MLN-3897 impairs infection by SARS-CoV-2 in vitro [2].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 65.82
Molecular weight 532.25
XLogP 5.27
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES Clc1ccc(cc1)C1(O)CCN(CC1(C)C)CC/C=C\1/c2cc(ccc2OCc2c1cccn2)C(O)(C)C
Isomeric SMILES Clc1ccc(cc1)C1(O)CCN(CC1(C)C)CC/C=C\1/c2cc(ccc2OCc2c1cccn2)C(O)(C)C
InChI InChI=1S/C32H37ClN2O3/c1-30(2)21-35(18-15-32(30,37)22-9-12-24(33)13-10-22)17-6-8-25-26-7-5-16-34-28(26)20-38-29-14-11-23(19-27(25)29)31(3,4)36/h5,7-14,16,19,36-37H,6,15,17-18,20-21H2,1-4H3/b25-8+
InChI Key ZGFJFBOLVLFLLN-ZNLRHDTNSA-N
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
AVE-9897 | AVE9897 | MLN3897
Database Links Click here for help
Specialist databases
GPCRdb Ligand MLN-3897
Other databases
GtoPdb PubChem SID 405560191
PubChem CID 18437138
Search Google for chemical match using the InChIKey ZGFJFBOLVLFLLN-ZNLRHDTNSA-N
Search Google for chemicals with the same backbone ZGFJFBOLVLFLLN
UniChem Compound Search for chemical match using the InChIKey ZGFJFBOLVLFLLN-ZNLRHDTNSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZGFJFBOLVLFLLN-ZNLRHDTNSA-N