Trimetozine

ID: ALA1697853

Cas Number: 635-41-6

PubChem CID: 12478

Product Number: T693505, Order Now?

Max Phase: Phase

Molecular Formula: C14H19NO5

Molecular Weight: 281.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Trimolide | ABBOTT-22370 | NSC-62939 | PS 2383 | PS-2383 | TRIMETOZINE|635-41-6|Sedoxazine|Trioxazin|Trioxazine|Trimethoxazine|Trifenoxazin|Opalene|4-(3,4,5-Trimethoxybenzoyl)morpholine|Trimetozin|Triksazin|Abbott-22370|Trimetozina|NSC-62939|Morpholine, 4-(3,4,5-trimethoxybenzoyl)-|PS 2383|NSC 62939|Trimetogine|Trimolide|LG 50043|PS-2383|N-(3,4,5-Trimethoxybenzoyl)morpholine|A 22370|4-(3,4,5-Trimethoxybenzoyl)tetrahydro-1,4-oxazine|N-(3,4,5-Trimethoxybenzoyl)tetrahydro-1,4-oxazine|3,4,5-TrimethoShow More⌵

Canonical SMILES:  COc1cc(C(=O)N2CCOCC2)cc(OC)c1OC

Standard InChI:  InChI=1S/C14H19NO5/c1-17-11-8-10(9-12(18-2)13(11)19-3)14(16)15-4-6-20-7-5-15/h8-9H,4-7H2,1-3H3

Standard InChI Key:  XWVOEFLBOSSYGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -0.5708   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583   -0.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833    0.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    1.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    2.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  1  1  0
  5  8  2  0
  6  7  1  0
  7  2  2  0
  8  2  1  0
  9  1  2  0
 10 16  1  0
 11  3  1  0
 12  6  1  0
 13  5  1  0
 14  4  1  0
 15  4  1  0
 16 15  1  0
 17 14  1  0
 18 11  1  0
 19 12  1  0
 20 13  1  0
 17 10  1  0
  6  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1697853

   Trimetozine

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 281.31

Molecular Weight (Monoisotopic): 281.1263

AlogP: 1.18

#Rotatable Bonds: 4

Polar Surface Area: 57.23

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -0.93

References

1. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

6. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

7. 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]

8. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

9. 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]

10. 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]

11. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

12. 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(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6