ID: ALA508044

Max Phase: Preclinical

Molecular Formula: C27H27ClN4O5

Molecular Weight: 522.99

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COc1cccc(OC)c1-c1cc(C(=O)N[C@@H](CC(C)C)C(=O)O)nn1-c1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C27H27ClN4O5/c1-15(2)12-20(27(34)35)30-26(33)19-14-22(25-23(36-3)6-5-7-24(25)37-4)32(31-19)21-10-11-29-18-13-16(28)8-9-17(18)21/h5-11,13-15,20H,12H2,1-4H3,(H,30,33)(H,34,35)/t20-/m0/s1

Standard InChI Key:  ZQUSYVORYNBGLG-FQEVSTJZSA-N

Associated Targets(Human)

Neurotensin receptor 1 1525 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Dopamine transporter 10535 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mu opioid receptor 19785 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Delta opioid receptor 15096 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Liver microsome 8277 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Plasma 7708 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

G-protein coupled receptor 35 2643 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Neurotensin receptor 2 296 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Histone deacetylase 6 20808 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasma 6361 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SARS-CoV-2 38078 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Replicase polyprotein 1ab 11336 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

Properties

Molecular Weight: 522.99Molecular Weight (Monoisotopic): 522.1670AlogP: 4.99#Rotatable Bonds: 9
Polar Surface Area: 115.57Molecular Species: ACIDHBA: 7HBD: 2
#RO5 Violations: 1HBA (Lipinski): 9HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.39CX Basic pKa: 5.23CX LogP: 3.44CX LogD: 1.59
Aromatic Rings: 4Heavy Atoms: 37QED Weighted: 0.32Np Likeness Score: -0.77

References

1. Thomas JB, Navarro H, Warner KR, Gilmour B..  (2009)  The identification of nonpeptide neurotensin receptor partial agonists from the potent antagonist SR48692 using a calcium mobilization assay.,  19  (5): [PMID:19195889] [10.1016/j.bmcl.2009.01.024]
2. Peddibhotla S, Hedrick MP, Hershberger P, Maloney PR, Li Y, Milewski M, Gosalia P, Gray W, Mehta A, Sugarman E, Hood B, Suyama E, Nguyen K, Heynen-Genel S, Vasile S, Salaniwal S, Stonich D, Su Y, Mangravita-Novo A, Vicchiarelli M, Roth GP, Smith LH, Chung TD, Hanson GR, Thomas JB, Caron MG, Barak LS, Pinkerton AB..  (2013)  Discovery of ML314, a Brain Penetrant Non-Peptidic β-Arrestin Biased Agonist of the Neurotensin NTR1 Receptor.,  (9): [PMID:24611085] [10.1021/ml400176n]
3. Hershberger PM, Hedrick MP, Peddibhotla S, Mangravita-Novo A, Gosalia P, Li Y, Gray W, Vicchiarelli M, Smith LH, Chung TD, Thomas JB, Caron MG, Pinkerton AB, Barak LS, Roth GP..  (2014)  Imidazole-derived agonists for the neurotensin 1 receptor.,  24  (1): [PMID:24332089] [10.1016/j.bmcl.2013.11.026]
4. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
5. 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]
6. 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]
7. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]