SID24424590

ID: ALA1474963

Cas Number: 1477-19-6

PubChem CID: 255968

Product Number: B131893, Order Now?

Max Phase: Approved

Molecular Formula: C17H14O3

Molecular Weight: 266.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: L 2197 | L-2197 | NSC-82134 | Benzarone|1477-19-6|(2-Ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone|Vasoc|Fragivix|Venagil|Benzarona|Benzaronum|Fagivil|Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-|2-Ethyl-3-benzofuranyl p-hydroxyphenyl ketone|2-Ethyl-3-(4-hydroxybenzoyl)benzofuran|L 2197|NSC 82134|2-Ethyl-3-(p-hydroxybenzoyl)benzofuran|2-Ethyl-4'-hydroxy-3-benzoylbenzofuran|(2-ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone|NSC-82134|KETONE, 2-ETHYL-3-BENZOFURANYL p-HYDROXYPHENYL|2Show More⌵

Canonical SMILES:  CCc1oc2ccccc2c1C(=O)c1ccc(O)cc1

Standard InChI:  InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3

Standard InChI Key:  RFRXIWQYSOIBDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -1.0208   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -2.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667    2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    1.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  5  2  0
  7  4  1  0
  8  4  2  0
  9  7  2  0
 10  7  1  0
 11  2  1  0
 12 13  1  0
 13 10  2  0
 14  9  1  0
 15 12  1  0
 16  5  1  0
 17  6  1  0
 18 11  1  0
 19 16  2  0
 20 19  1  0
  6  3  1  0
 17 20  2  0
 14 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1474963

   BENZARONE

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: 266.30

Molecular Weight (Monoisotopic): 266.0943

AlogP: 3.93

#Rotatable Bonds: 3

Polar Surface Area: 50.44

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.80

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 3.86

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 0.32

References

1. PubChem BioAssay data set, 

2. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

3. Wempe MF, Jutabha P, Quade B, Iwen TJ, Frick MM, Ross IR, Rice PJ, Anzai N, Endou H..  (2011)  Developing potent human uric acid transporter 1 (hURAT1) inhibitors.,  54  (8): [PMID:21449597] [10.1021/jm1015022]

4. Chen M, Vijay V, Shi Q, Liu Z, Fang H, Tong W..  (2011)  FDA-approved drug labeling for the study of drug-induced liver injury.,  16  (15-16): [PMID:21624500] [10.1016/j.drudis.2011.05.007]

5. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

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

7. Gordon CP, Williams P, Chan WC..  (2013)  Attenuating Staphylococcus aureus virulence gene regulation: a medicinal chemistry perspective.,  56  (4): [PMID:23294220] [10.1021/jm3014635]

8. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

9. Unpublished dataset, 

10. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

11.  (2016)  Use of small molecule inhibitors targeting eya tyrosine phosphatase, 

12. 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]

13.  (2017)  Use of small molecule inhibitors targeting EYA tyrosine phosphatase, 

14. Rana P, Will Y, Nadanaciva S, Jones LH..  (2016)  Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.,  26  (16): [PMID:27397500] [10.1016/j.bmcl.2016.06.088]

15. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

16.  (2021)  Inhibitors of eya3-protein tyrosine phosphatase in dna damage repair signaling of pulmonary arterial hypertension, 

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• Withdrawn Drugs
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21