ID: ALA93347

Max Phase: Preclinical

Molecular Formula: C14H8O3S

Molecular Weight: 256.28

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)c1cc2c(s1)C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C14H8O3S/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3

Standard InChI Key:  AZJPKGXMDKTLMO-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 256.28

Molecular Weight (Monoisotopic): 256.0194

AlogP: 2.73

#Rotatable Bonds: 1

Polar Surface Area: 51.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.63

Np Likeness Score: -0.07

References

1. Huang LJ, Kuo SC, Perng CY, Chao YH, Wu TS, McPhail AT, Mauger A, Cheng HH, Lee KH..  (1998)  Synthesis and cytotoxicity of acetyl-4H,9H-naphtho[2,3-b]thiophene-4,9-diones.,  8  (19): [PMID:9873618] [10.1016/s0960-894x(98)00496-x]

2. PubChem BioAssay data set, 

3. Bannwitz S, Krane D, Vortherms S, Kalin T, Lindenschmidt C, Zahedi Golpayegani N, Tentrop J, Prinz H, Müller K..  (2014)  Synthesis and structure-activity relationships of lapacho analogues. 2. Modification of the basic naphtho[2,3-b]furan-4,9-dione, redox activation, and suppression of human keratinocyte hyperproliferation by 8-hydroxynaphtho[2,3-b]thiophene-4,9-diones.,  57  (14): [PMID:24964246] [10.1021/jm500754d]

4. Lindenschmidt C, Krane D, Vortherms S, Hilbig L, Prinz H, Müller K..  (2016)  8-Halo-substituted naphtho[2,3-b]thiophene-4,9-diones as redox-active inhibitors of keratinocyte hyperproliferation with reduced membrane-damaging properties.,  110  [PMID:26840368] [10.1016/j.ejmech.2016.01.040]

5. Basoglu A, Dirkmann S, Zahedi Golpayegani N, Vortherms S, Tentrop J, Nowottnik D, Prinz H, Fröhlich R, Müller K..  (2017)  Oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure-activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent.,  134  [PMID:28410493] [10.1016/j.ejmech.2017.03.084]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays