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Analysis presented in a bioRxiv preprint (not peer reviewed) suggests that MLN-3897 impairs infection by SARS-CoV-2 in vitro [2].
2D Structure
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Physico-chemical Properties
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
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+
Compound class Synthetic organic
AVE-9897 | AVE9897 | MLN3897
Database Links
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
Search UniChem for chemical match using the InChIKey ZGFJFBOLVLFLLN-ZNLRHDTNSA-N
Search UniChem for chemicals with the same backbone ZGFJFBOLVLFLLN