ID: ALA62539

Max Phase: Preclinical

Molecular Formula: C12H6O3

Molecular Weight: 198.18

Molecule Type: Small molecule

Representations

Synonyms (1): Avicequinone-B
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1c2ccccc2C(=O)c2occc21

Standard InChI:  InChI=1S/C12H6O3/c13-10-7-3-1-2-4-8(7)11(14)12-9(10)5-6-15-12/h1-6H

Standard InChI Key:  QMKMOPXRLXYBLI-UHFFFAOYSA-N

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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 198.18

Molecular Weight (Monoisotopic): 198.0317

AlogP: 2.06

#Rotatable Bonds: 0

Polar Surface Area: 47.28

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.56

Np Likeness Score: 0.75

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. Wu C, Johnson RK, Mattern MR, Wong JC, Kingston DG..  (1999)  Synthesis of furanonaphthoquinones with hydroxyamino side chains.,  62  (7): [PMID:10425117] [10.1021/np9900019]

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. Tseng CH, Chen YL, Yang SH, Peng SI, Cheng CM, Han CH, Lin SR, Tzeng CC..  (2010)  Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.,  18  (14): [PMID:20591678] [10.1016/j.bmc.2010.05.062]

5. Reichstein A, Vortherms S, Bannwitz S, Tentrop J, Prinz H, Müller K..  (2012)  Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.,  55  (16): [PMID:22845014] [10.1021/jm3009597]

6. Löcken H, Clamor C, Müller K..  (2018)  Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.,  81  (7): [PMID:30003778] [10.1021/acs.jnatprod.8b00247]

Source

Source(1):

• Scientific Literature