ID: ALA443793

Max Phase: Phase

Molecular Formula: C17H12O4

Molecular Weight: 280.28

Molecule Type: Small molecule

Representations

Synonyms (2): Mitoflaxone | NSC-347512
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C(O)Cc1cccc2c(=O)cc(-c3ccccc3)oc12

Standard InChI:  InChI=1S/C17H12O4/c18-14-10-15(11-5-2-1-3-6-11)21-17-12(9-16(19)20)7-4-8-13(14)17/h1-8,10H,9H2,(H,19,20)

Standard InChI Key:  TZZNWMJZDWYJAZ-UHFFFAOYSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 280.28

Molecular Weight (Monoisotopic): 280.0736

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 67.51

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.68

CX Basic pKa:

CX LogP: 2.61

CX LogD: -0.71

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: 0.42

References

1. Rewcastle GW, Atwell GJ, Li ZA, Baguley BC, Denny WA..  (1991)  Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids.,  34  (1): [PMID:1992120] [10.1021/jm00105a034]

2. Aitken R, Bibby MC, Double JA, Phillips RM, Sharma SK.  (1994)  Synthesis and anti-tumour activity of 6-methyl derivatives of flavone-8-acetic acid (FAA),  4  (19): [10.1016/0960-894X(94)85031-3]

3. Gobbi S, Rampa A, Bisi A, Belluti F, Piazzi L, Valenti P, Caputo A, Zampiron A, Carrara M..  (2003)  Synthesis and biological evaluation of 3-alkoxy analogues of flavone-8-acetic acid.,  46  (17): [PMID:12904070] [10.1021/jm030771o]

4. Bauvois B, Puiffe ML, Bongui JB, Paillat S, Monneret C, Dauzonne D..  (2003)  Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13.,  46  (18): [PMID:12930151] [10.1021/jm021109f]

5. Rewcastle GW, Atwell GJ, Baguley BC, Calveley SB, Denny WA..  (1989)  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo.,  32  (4): [PMID:2704025] [10.1021/jm00124a012]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

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

9. Zhou ZZ, Gu CP, Deng YH, Yan GH, Li XF, Yu L, Chen WH, Liu SW..  (2014)  Synthesis, selective cytotoxicities and probable mechanism of action of 7-methoxy-3-arylflavone-8-acetic acids.,  22  (5): [PMID:24518295] [10.1016/j.bmc.2014.01.042]

10. 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]

11. 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]

12. 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]

13. 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(5):

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