ID: ALA302418

Max Phase: Preclinical

Molecular Formula: C12H6O2S

Molecular Weight: 214.25

Molecule Type: Small molecule

Representations

Synonyms (1): Thiophenonaphthoquinone
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1c2ccccc2C(=O)c2sccc21

Standard InChI:  InChI=1S/C12H6O2S/c13-10-7-3-1-2-4-8(7)11(14)12-9(10)5-6-15-12/h1-6H

Standard InChI Key:  GDUFLCCHLCZVCJ-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: 214.25

Molecular Weight (Monoisotopic): 214.0089

AlogP: 2.52

#Rotatable Bonds: 0

Polar Surface Area: 34.14

Molecular Species:

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.83

CX LogD: 2.83

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.58

Np Likeness Score: -0.16

References

1. Goulart MO, Zani CL, Tonholo J, Freitas LR, de Abreu FC, Oliveira AB, Raslan DS, Starling S, Chiari E.  (1997)  Trypanocidal activity and redox potential of heterocyclic- and 2-hydroxy-naphthoquinones,  7  (15): [10.1016/S0960-894X(97)00354-5]

2. 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]

3. Konoshima T, Kozuka M, Koyama J, Okatani T, Tagahara K, Tokuda H..  (1989)  Studies on inhibitors of skin tumor promotion, VI. Inhibitory effects of quinones on Epstein-Barr virus activation.,  52  (5): [PMID:2558164] [10.1021/np50065a012]

4. 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]

5. 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]

6. 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]

7. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data