ID: ALA274056

Max Phase: Preclinical

Molecular Formula: C10H6O4

Molecular Weight: 190.15

Molecule Type: Small molecule

Representations

Synonyms (2): 5,8-Dihydroxy-[1,4]Naphthoquinone | Naphthazalin
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C1C=CC(=O)c2c(O)ccc(O)c21

Standard InChI:  InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H

Standard InChI Key:  RQNVIKXOOKXAJQ-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: 190.15

Molecular Weight (Monoisotopic): 190.0266

AlogP: 1.03

#Rotatable Bonds: 0

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.54

CX Basic pKa:

CX LogP: 2.19

CX LogD: 2.16

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.60

Np Likeness Score: 1.17

References

1. Tandon VK, Chhor RB, Singh RV, Rai S, Yadav DB..  (2004)  Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents.,  14  (5): [PMID:14980639] [10.1016/j.bmcl.2004.01.002]

2. Plyta ZF, Li T, Papageorgiou VP, Mellidis AS, Assimopoulou AN, Pitsinos EN, Couladouros EA..  (1998)  Inhibition of topoisomerase I by naphthoquinone derivatives.,  8  (23): [PMID:9873739] [10.1016/s0960-894x(98)00600-3]

3. Müller K, Prinz H, Gawlik I, Ziereis K, Huang HS..  (1997)  Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.,  40  (23): [PMID:9371243] [10.1021/jm970292n]

4. Tandon VK, Yadav DB, Chaturvedi AK, Shukla PK..  (2005)  Synthesis of (1,4)-naphthoquinono-[3,2-c]-1H-pyrazoles and their (1,4)-naphthohydroquinone derivatives as antifungal, antibacterial, and anticancer agents.,  15  (13): [PMID:15913995] [10.1016/j.bmcl.2005.04.066]

5. Millet R, Urig S, Jacob J, Amtmann E, Moulinoux JP, Gromer S, Becker K, Davioud-Charvet E..  (2005)  Synthesis of 5-nitro-2-furancarbohydrazides and their cis-diamminedichloroplatinum complexes as bitopic and irreversible human thioredoxin reductase inhibitors.,  48  (22): [PMID:16250662] [10.1021/jm050256l]

6. 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]

7. Cao S, Murphy BT, Foster C, Lazo JS, Kingston DG..  (2009)  Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases.,  17  (6): [PMID:19028102] [10.1016/j.bmc.2008.10.090]

8. PubChem BioAssay data set, 

9. Fischer TC, Gosch C, Mirbeth B, Gselmann M, Thallmair V, Stich K..  (2012)  Potent and specific bactericidal effect of juglone (5-hydroxy-1,4-naphthoquinone) on the fire blight pathogen Erwinia amylovora.,  60  (49): [PMID:23163769] [10.1021/jf303584r]

10. Akhtar Y, Isman MB, Niehaus LA, Lee CH, Lee HS..  (2012)  Antifeedant and toxic effects of naturally occurring and synthetic quinones to the cabbage looper, Trichoplusia ni,  31  (1): [10.1016/j.cropro.2011.09.009]

11. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

12. Bremer PT, Hixon MS, Janda KD..  (2014)  Benzoquinones as inhibitors of botulinum neurotoxin serotype A.,  22  (15): [PMID:24984937] [10.1016/j.bmc.2014.06.004]

13. Zhang J, Liu Y, Shi D, Hu G, Zhang B, Li X, Liu R, Han X, Yao X, Fang J..  (2017)  Synthesis of naphthazarin derivatives and identification of novel thioredoxin reductase inhibitor as potential anticancer agent.,  140  [PMID:28987605] [10.1016/j.ejmech.2017.09.027]

14. Joshi P, Sonawane VR, Williams IS, McCann GJP, Gatchie L, Sharma R, Satti N, Chaudhuri B, Bharate SB..  (2018)  Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository.,  9  (2): [PMID:30108931] [10.1039/C7MD00388A]

15. Furqan M, Fayyaz A, Firdous F, Raza H, Bilal A, Saleem RSZ, Shahzad-Ul-Hussan S, Wang D, Youssef FS, Al Musayeib NM, Ashour ML, Hussain H, Faisal A..  (2022)  Identification and Characterization of Natural and Semisynthetic Quinones as Aurora Kinase Inhibitors.,  85  (6.0): [PMID:35687347] [10.1021/acs.jnatprod.1c01222]

16. La Monica G, Bono A, Lauria A, Martorana A..  (2022)  Targeting SARS-CoV-2 Main Protease for Treatment of COVID-19: Covalent Inhibitors Structure-Activity Relationship Insights and Evolution Perspectives.,  65  (19.0): [PMID:36169610] [10.1021/acs.jmedchem.2c01005]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• AstraZeneca Deposited Data