ID: ALA582878

Max Phase: Preclinical

Molecular Formula: C12H13NO2

Molecular Weight: 203.24

Molecule Type: Small molecule

Representations

Synonyms (1): Indole-3-Butyric Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(O)CCCc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

Standard InChI Key:  JTEDVYBZBROSJT-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 203.24

Molecular Weight (Monoisotopic): 203.0946

AlogP: 2.58

#Rotatable Bonds: 4

Polar Surface Area: 53.09

Molecular Species: ACID

HBA: 1

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.86

CX Basic pKa:

CX LogP: 2.60

CX LogD: 0.10

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.80

Np Likeness Score: 0.12

References

1. Maillet EL, Margolskee RF, Mosinger B..  (2009)  Phenoxy herbicides and fibrates potently inhibit the human chemosensory receptor subunit T1R3.,  52  (21): [PMID:19817384] [10.1021/jm900823s]

2. PubChem BioAssay data set, 

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

4. Katayama M, Masui Y, Kageyama E, Kawabata Y, Kanayama K..  (2008)  Synthesis and biological activities of 4-trifluoromethylindole-3-acetic acid: a new fluorinated indole auxin.,  72  (8): [PMID:18685200] [10.1271/bbb.80138]

5. Abdel-Aty AS.  (2010)  Fungicidal activity of indole derivatives against some plant pathogenic fungi,  35  (4): [10.1584/jpestics.G09-66]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. Christopeit T, Carlsen TJ, Helland R, Leiros HK..  (2015)  Discovery of Novel Inhibitor Scaffolds against the Metallo-β-lactamase VIM-2 by Surface Plasmon Resonance (SPR) Based Fragment Screening.,  58  (21): [PMID:26477515] [10.1021/acs.jmedchem.5b01289]

9. Christopeit T, Leiros HK..  (2016)  Fragment-based discovery of inhibitor scaffolds targeting the metallo-β-lactamases NDM-1 and VIM-2.,  26  (8): [PMID:26976213] [10.1016/j.bmcl.2016.03.004]

10. Lund BA, Christopeit T, Guttormsen Y, Bayer A, Leiros HK..  (2016)  Screening and Design of Inhibitor Scaffolds for the Antibiotic Resistance Oxacillinase-48 (OXA-48) through Surface Plasmon Resonance Screening.,  59  (11): [PMID:27165692] [10.1021/acs.jmedchem.6b00660]

11. Hu C, Ma S..  (2018)  Recent development of lipoxygenase inhibitors as anti-inflammatory agents.,  9  (2): [PMID:30108915] [10.1039/C7MD00390K]

12. 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]

13. 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]

14. 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]

15. 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]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6