Naphtho[2,3-b]furan-4,9-dione

ID: ALA62539

Chembl Id: CHEMBL62539

Cas Number: 5656-82-6

PubChem CID: 79740

Max Phase: Preclinical

Molecular Formula: C12H6O3

Molecular Weight: 198.18

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Avicequinone-B | Naphtho[2,3-b]furan-4,9-dione|5656-82-6|benzo[f][1]benzofuran-4,9-dione|Naphtho(2,3-b)furan-4,9-dione|Npf-4,9-dione|Avicequinone-B|SCHEMBL28782|CHEMBL62539|DTXSID00205114|Furan, 2,3-(1,2-phenylenedicarbonyl)-|4H,9H-NAPHTHO[2,3-B]FURAN-4,9-DIONE

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

Alternative Forms

Associated Targets(Human)

Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Detroit 551 (346 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HaCaT (4069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NQO1 NQO1 protein (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POR Tbio NADPH--cytochrome P450 reductase (112 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 198.18Molecular Weight (Monoisotopic): 198.0317AlogP: 2.06#Rotatable Bonds:
Polar Surface Area: 47.28Molecular Species: NEUTRALHBA: 3HBD:
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 1.98CX LogD: 1.98
Aromatic Rings: 2Heavy Atoms: 15QED Weighted: 0.56Np 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,  (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