N-(2-((3S,4S)-1-(cis-4-(benzo[d][1,3]dioxol-5-yl)-4-hydroxycyclohexyl)-4-ethoxypyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide

ID: ALA1289316

Chembl Id: CHEMBL1289316

Max Phase: Preclinical

Molecular Formula: C29H34F3N3O6

Molecular Weight: 577.60

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: INCB-3344

Canonical SMILES:  CCO[C@H]1CN([C@H]2CC[C@@](O)(c3ccc4c(c3)OCO4)CC2)C[C@@H]1NC(=O)CNC(=O)c1cccc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C29H34F3N3O6/c1-2-39-25-16-35(21-8-10-28(38,11-9-21)19-6-7-23-24(13-19)41-17-40-23)15-22(25)34-26(36)14-33-27(37)18-4-3-5-20(12-18)29(30,31)32/h3-7,12-13,21-22,25,38H,2,8-11,14-17H2,1H3,(H,33,37)(H,34,36)/t21-,22-,25-,28-/m0/s1

Standard InChI Key:  MZEOSVPWMSEFPW-UTWBDPIXSA-N

Alternative Forms

  1. Parent:

    ALA1289316

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Associated Targets(Human)

CCR2 Tchem C-C chemokine receptor type 2 (5628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Serum (1292 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Ccr2 C-C chemokine receptor type 2 (106 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Serum (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ccr2 C-C chemokine receptor type 2 (8 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR2 protein (1 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ccr1 C-C chemokine receptor type 1 (74 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ccr5 C-C chemokine receptor type 5 (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 577.60Molecular Weight (Monoisotopic): 577.2400AlogP: 3.20#Rotatable Bonds: 8
Polar Surface Area: 109.36Molecular Species: NEUTRALHBA: 7HBD: 3
#RO5 Violations: 1HBA (Lipinski): 9HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.78CX Basic pKa: 8.43CX LogP: 2.78CX LogD: 1.71
Aromatic Rings: 2Heavy Atoms: 41QED Weighted: 0.44Np Likeness Score: -0.53

References

1. Xue CB, Wang A, Meloni D, Zhang K, Kong L, Feng H, Glenn J, Huang T, Zhang Y, Cao G, Anand R, Zheng C, Xia M, Han Q, Robinson DJ, Storace L, Shao L, Li M, Brodmerkel CM, Covington M, Scherle P, Diamond S, Yeleswaram S, Vaddi K, Newton R, Hollis G, Friedman S, Metcalf B..  (2010)  Discovery of INCB3344, a potent, selective and orally bioavailable antagonist of human and murine CCR2.,  20  (24): [PMID:21036044] [10.1016/j.bmcl.2010.10.020]
2. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
3. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]