2-(4-hydroxyanilino)-1,4-naphthoquinone profile

2-(4-hydroxyanilino)-1,4-naphthoquinone, also known as **Lawsone** or **Henna**, is a natural dye obtained from the henna plant ( _Lawsonia inermis_).

**Importance for Research:**

Lawsone has been investigated extensively due to its diverse biological activities and potential applications in various research fields:

* **Antioxidant properties:** Lawsone exhibits potent antioxidant activity, scavenging free radicals and protecting cells from oxidative damage. This property has been explored for its potential benefits in preventing aging, cancer, and other diseases.
* **Anti-inflammatory properties:** Lawsone has shown anti-inflammatory effects in various studies, reducing inflammation and pain in models of inflammatory diseases.
* **Antibacterial and antifungal properties:** Lawsone exhibits antibacterial and antifungal activity against a wide range of microorganisms, making it a promising agent for treating infections.
* **Anti-cancer properties:** Studies have indicated that Lawsone might possess anti-cancer properties, inducing cell death in cancer cells and inhibiting their growth and spread.
* **Wound healing:** Lawsone has traditionally been used for wound healing, and research suggests it can promote wound closure and tissue regeneration.
* **Cosmetics and skincare:** Lawsone is the primary pigment in henna, used for temporary skin and hair dyeing. Research focuses on developing safer and more effective henna-based products for cosmetic applications.
* **Bioimaging:** Lawsone has been investigated as a potential fluorescent probe for bioimaging applications, allowing researchers to visualize specific cellular components or processes.

**Ongoing Research:**

Current research on Lawsone is exploring its:

* Mechanisms of action: Investigating how Lawsone interacts with cellular targets to exert its various biological effects.
* Potential drug development: Studying the feasibility of developing Lawsone-based drugs for treating different diseases.
* Safety and toxicity: Determining the safe and effective dosage of Lawsone for various applications and identifying potential side effects.
* Potential interactions with other drugs: Investigating how Lawsone might interact with other medications, which is crucial for safe and effective treatment.

In conclusion, 2-(4-hydroxyanilino)-1,4-naphthoquinone (Lawsone) is a natural compound with a wide range of biological activities and potential applications in various research fields, including medicine, cosmetics, and bioimaging. Further research is ongoing to understand its mechanisms of action, safety, and potential for developing new therapeutic agents.

2-(4-hydroxyanilino)-1,4-naphthoquinone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	739245
CHEMBL ID	1631459
CHEMBL ID	1972249
MeSH ID	M0585542

Synonym
CBDIVE_004489
2-(4-hydroxy-phenylamino)-[1,4]naphthoquinone
MLS000778717 ,
smr000415498
STK386862
2-[(4-hydroxyphenyl)amino]naphthalene-1,4-dione
2-(4-hydroxyanilino)naphthalene-1,4-dione
CHEMBL1631459
AKOS001582697
HMS2757P10
2-(4-hydroxyanilino)-1,4-naphthoquinone
cid_739245
bdbm47462
CHEMBL1972249
2-[(4-hydroxyphenyl)amino]-1,4-dihydronaphthalene-1,4-dione
BLXXUTVXRNZUQX-UHFFFAOYSA-N
sr-01000106189
SR-01000106189-1
SR-01000106189-2

Excerpt	Reference	Relevance
"The purpose of the study was to obtain further in vivo data of antitumor effects and mechanisms triggered by juglone and Q7 in combination with ascorbate."	( In vivo inhibition of tumor progression by 5 hydroxy-1,4-naphthoquinone (juglone) and 2-(4-hydroxyanilino)-1,4-naphthoquinone (Q7) in combination with ascorbate. Benites, J; Calderon, PB; Castro, LSEPW; Gomes Castro, AJ; Kviecinski, MR; Mena Barreto Silva, FR; Ourique, F; Pedrosa, RC; Rios, D; Valderrama, JA; Zirbel, G, 2016)	0.66

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	79.4328	0.0040	23.8416	100.0000	AID485290
Chain A, Beta-lactamase	Escherichia coli K-12	Potency	89.1251	0.0447	17.8581	100.0000	AID485294
Chain A, Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	7.0627	0.1409	11.1940	39.8107	AID2451
Chain A, JmjC domain-containing histone demethylation protein 3A	Homo sapiens (human)	Potency	11.2202	0.6310	35.7641	100.0000	AID504339
Luciferase	Photinus pyralis (common eastern firefly)	Potency	5.3582	0.0072	15.7588	89.3584	AID588342
BRCA1	Homo sapiens (human)	Potency	35.4813	0.8913	7.7225	25.1189	AID624202
WRN	Homo sapiens (human)	Potency	50.1187	0.1683	31.2583	100.0000	AID651768
ATAD5 protein, partial	Homo sapiens (human)	Potency	4.7092	0.0041	10.8903	31.5287	AID504466; AID504467
GLS protein	Homo sapiens (human)	Potency	19.9526	0.3548	7.9355	39.8107	AID624170
TDP1 protein	Homo sapiens (human)	Potency	13.7882	0.0008	11.3822	44.6684	AID686978; AID686979
Microtubule-associated protein tau	Homo sapiens (human)	Potency	26.2000	0.1800	13.5574	39.8107	AID1460; AID1468
thioredoxin glutathione reductase	Schistosoma mansoni	Potency	79.4328	0.1000	22.9075	100.0000	AID485364
Smad3	Homo sapiens (human)	Potency	10.0000	0.0052	7.8098	29.0929	AID588855
apical membrane antigen 1, AMA1	Plasmodium falciparum 3D7	Potency	28.1838	0.7079	12.1943	39.8107	AID720542
nonstructural protein 1	Influenza A virus (A/WSN/1933(H1N1))	Potency	7.9433	0.2818	9.7212	35.4813	AID2326
67.9K protein	Vaccinia virus	Potency	29.9033	0.0001	8.4406	100.0000	AID720579; AID720580
bromodomain adjacent to zinc finger domain 2B	Homo sapiens (human)	Potency	28.1838	0.7079	36.9043	89.1251	AID504333
P53	Homo sapiens (human)	Potency	12.5893	0.0731	9.6858	31.6228	AID504706
pyruvate kinase	Leishmania mexicana mexicana	Potency	7.9433	0.3981	13.7447	31.6228	AID1721; AID1722
IDH1	Homo sapiens (human)	Potency	25.9290	0.0052	10.8652	35.4813	AID686970
Bloom syndrome protein isoform 1	Homo sapiens (human)	Potency	28.1838	0.5406	17.6392	96.1227	AID2528
mitogen-activated protein kinase 1	Homo sapiens (human)	Potency	28.1838	0.0398	16.7842	39.8107	AID1454
ras-related protein Rab-9A	Homo sapiens (human)	Potency	3.5481	0.0002	2.6215	31.4954	AID485297
eyes absent homolog 2 isoform a	Homo sapiens (human)	Potency	7.5699	1.1998	14.6419	50.1187	AID720540
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens (human)	Potency	37.9330	0.4256	12.0591	28.1838	AID504891
DNA polymerase eta isoform 1	Homo sapiens (human)	Potency	19.9526	0.1000	28.9256	213.3130	AID588591
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	100.0000	0.0501	27.0736	89.1251	AID588590
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	35.4813	0.0079	8.2332	1,122.0200	AID2546
geminin	Homo sapiens (human)	Potency	24.8446	0.0046	11.3741	33.4983	AID624296; AID624297
Vpr	Human immunodeficiency virus 1	Potency	7.0795	1.5849	19.6264	63.0957	AID651644
muscleblind-like protein 1 isoform 1	Homo sapiens (human)	Potency	3.1623	0.0041	9.9625	28.1838	AID2675
Glycoprotein hormones alpha chain	Homo sapiens (human)	Potency	11.2202	4.4668	8.3448	10.0000	AID624291
Endothelin receptor type B	Rattus norvegicus (Norway rat)	Potency	7.9433	0.5623	15.1609	31.6228	AID1721
Endothelin-1 receptor	Rattus norvegicus (Norway rat)	Potency	7.9433	0.5623	15.1609	31.6228	AID1721
C-terminal-binding protein 1	Homo sapiens (human)	Potency	6.7467	0.3014	9.3210	19.0148	AID720541
phosphoglycerate kinase	Trypanosoma brucei brucei TREU927	Potency	25.1189	0.0757	8.4742	29.0628	AID602233
ATP-dependent phosphofructokinase	Trypanosoma brucei brucei TREU927	Potency	19.0115	0.0601	10.7453	37.9330	AID485367
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
calpain II, partial	Sus scrofa (pig)	IC50 (µMol)	5.0958	1.7742	4.9338	7.7087	AID1420
Janus kinase 2 (a protein tyrosine kinase)	Homo sapiens (human)	IC50 (µMol)	7.5320	0.2230	4.2372	7.5320	AID1699
rac GTPase-activating protein 1 isoform a	Homo sapiens (human)	IC50 (µMol)	23.7200	7.3900	57.8904	301.2400	AID624330
Ephrin type-B receptor 2	Homo sapiens (human)	IC50 (µMol)	38.0000	0.0025	1.5875	8.5000	AID240825
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
recombinase A	Mycobacterium tuberculosis H37Rv	EC50 (µMol)	3.6095	0.0180	23.2882	287.6000	AID434968; AID435010
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
replicative DNA helicase	Mycobacterium tuberculosis H37Rv	AC50	146.3900	0.0570	30.7482	325.3000	AID449749; AID449750
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
G protein-coupled receptor signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of cell population proliferation	Glycoprotein hormones alpha chain	Homo sapiens (human)
hormone-mediated signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
regulation of signaling receptor activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of steroid biosynthetic process	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of cell migration	Glycoprotein hormones alpha chain	Homo sapiens (human)
thyroid gland development	Glycoprotein hormones alpha chain	Homo sapiens (human)
luteinizing hormone secretion	Glycoprotein hormones alpha chain	Homo sapiens (human)
organ growth	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Glycoprotein hormones alpha chain	Homo sapiens (human)
negative regulation of organ growth	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone secretion	Glycoprotein hormones alpha chain	Homo sapiens (human)
thyroid hormone generation	Glycoprotein hormones alpha chain	Homo sapiens (human)
negative regulation of protein kinase activity	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of autophagosome assembly	Ephrin type-B receptor 2	Homo sapiens (human)
angiogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
urogenital system development	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of protein phosphorylation	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of immunoglobulin production	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of cell adhesion	Ephrin type-B receptor 2	Homo sapiens (human)
nervous system development	Ephrin type-B receptor 2	Homo sapiens (human)
axon guidance	Ephrin type-B receptor 2	Homo sapiens (human)
axonal fasciculation	Ephrin type-B receptor 2	Homo sapiens (human)
learning or memory	Ephrin type-B receptor 2	Homo sapiens (human)
learning	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of gene expression	Ephrin type-B receptor 2	Homo sapiens (human)
phosphorylation	Ephrin type-B receptor 2	Homo sapiens (human)
peptidyl-tyrosine phosphorylation	Ephrin type-B receptor 2	Homo sapiens (human)
optic nerve morphogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
hindbrain tangential cell migration	Ephrin type-B receptor 2	Homo sapiens (human)
central nervous system projection neuron axonogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
corpus callosum development	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of blood coagulation	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of cell migration	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of B cell proliferation	Ephrin type-B receptor 2	Homo sapiens (human)
retinal ganglion cell axon guidance	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of synaptic plasticity	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of tumor necrosis factor production	Ephrin type-B receptor 2	Homo sapiens (human)
B cell activation	Ephrin type-B receptor 2	Homo sapiens (human)
inner ear morphogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of receptor signaling pathway via JAK-STAT	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of Ras protein signal transduction	Ephrin type-B receptor 2	Homo sapiens (human)
ephrin receptor signaling pathway	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of neuronal synaptic plasticity	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of long-term neuronal synaptic plasticity	Ephrin type-B receptor 2	Homo sapiens (human)
camera-type eye morphogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of axonogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of body fluid levels	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of filopodium assembly	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of synapse assembly	Ephrin type-B receptor 2	Homo sapiens (human)
roof of mouth development	Ephrin type-B receptor 2	Homo sapiens (human)
dendritic spine development	Ephrin type-B receptor 2	Homo sapiens (human)
dendritic spine morphogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of dendritic spine morphogenesis	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascade	Ephrin type-B receptor 2	Homo sapiens (human)
cellular response to lipopolysaccharide	Ephrin type-B receptor 2	Homo sapiens (human)
commissural neuron axon guidance	Ephrin type-B receptor 2	Homo sapiens (human)
postsynaptic membrane assembly	Ephrin type-B receptor 2	Homo sapiens (human)
trans-synaptic signaling by trans-synaptic complex, modulating synaptic transmission	Ephrin type-B receptor 2	Homo sapiens (human)
neuron projection retraction	Ephrin type-B receptor 2	Homo sapiens (human)
vesicle-mediated intercellular transport	Ephrin type-B receptor 2	Homo sapiens (human)
tight junction assembly	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of cytokine production involved in inflammatory response	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of long-term synaptic potentiation	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of protein localization to plasma membrane	Ephrin type-B receptor 2	Homo sapiens (human)
cellular response to amyloid-beta	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of NMDA glutamate receptor activity	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of NMDA glutamate receptor activity	Ephrin type-B receptor 2	Homo sapiens (human)
positive regulation of protein localization to cell surface	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of T-helper 17 type immune response	Ephrin type-B receptor 2	Homo sapiens (human)
regulation of behavioral fear response	Ephrin type-B receptor 2	Homo sapiens (human)
protein phosphorylation	Ephrin type-B receptor 2	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	C-terminal-binding protein 1	Homo sapiens (human)
protein phosphorylation	C-terminal-binding protein 1	Homo sapiens (human)
negative regulation of cell population proliferation	C-terminal-binding protein 1	Homo sapiens (human)
viral genome replication	C-terminal-binding protein 1	Homo sapiens (human)
negative regulation of DNA-templated transcription	C-terminal-binding protein 1	Homo sapiens (human)
positive regulation of DNA-templated transcription	C-terminal-binding protein 1	Homo sapiens (human)
synaptic vesicle endocytosis	C-terminal-binding protein 1	Homo sapiens (human)
white fat cell differentiation	C-terminal-binding protein 1	Homo sapiens (human)
regulation of cell cycle	C-terminal-binding protein 1	Homo sapiens (human)
synaptic vesicle clustering	C-terminal-binding protein 1	Homo sapiens (human)
regulation of transcription by RNA polymerase II	C-terminal-binding protein 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
hormone activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
protein binding	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
amyloid-beta binding	Ephrin type-B receptor 2	Homo sapiens (human)
protein tyrosine kinase activity	Ephrin type-B receptor 2	Homo sapiens (human)
transmembrane-ephrin receptor activity	Ephrin type-B receptor 2	Homo sapiens (human)
signaling receptor binding	Ephrin type-B receptor 2	Homo sapiens (human)
protein binding	Ephrin type-B receptor 2	Homo sapiens (human)
ATP binding	Ephrin type-B receptor 2	Homo sapiens (human)
axon guidance receptor activity	Ephrin type-B receptor 2	Homo sapiens (human)
identical protein binding	Ephrin type-B receptor 2	Homo sapiens (human)
protein-containing complex binding	Ephrin type-B receptor 2	Homo sapiens (human)
transcription corepressor binding	C-terminal-binding protein 1	Homo sapiens (human)
chromatin binding	C-terminal-binding protein 1	Homo sapiens (human)
transcription corepressor activity	C-terminal-binding protein 1	Homo sapiens (human)
protein binding	C-terminal-binding protein 1	Homo sapiens (human)
oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor	C-terminal-binding protein 1	Homo sapiens (human)
protein domain specific binding	C-terminal-binding protein 1	Homo sapiens (human)
identical protein binding	C-terminal-binding protein 1	Homo sapiens (human)
NAD binding	C-terminal-binding protein 1	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	C-terminal-binding protein 1	Homo sapiens (human)
DNA-binding transcription factor binding	C-terminal-binding protein 1	Homo sapiens (human)
transcription coactivator activity	C-terminal-binding protein 1	Homo sapiens (human)
transcription coregulator binding	C-terminal-binding protein 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
extracellular region	Glycoprotein hormones alpha chain	Homo sapiens (human)
extracellular space	Glycoprotein hormones alpha chain	Homo sapiens (human)
Golgi lumen	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone complex	Glycoprotein hormones alpha chain	Homo sapiens (human)
pituitary gonadotropin complex	Glycoprotein hormones alpha chain	Homo sapiens (human)
extracellular space	Glycoprotein hormones alpha chain	Homo sapiens (human)
extracellular region	Ephrin type-B receptor 2	Homo sapiens (human)
nucleoplasm	Ephrin type-B receptor 2	Homo sapiens (human)
cytosol	Ephrin type-B receptor 2	Homo sapiens (human)
plasma membrane	Ephrin type-B receptor 2	Homo sapiens (human)
cell surface	Ephrin type-B receptor 2	Homo sapiens (human)
axon	Ephrin type-B receptor 2	Homo sapiens (human)
dendrite	Ephrin type-B receptor 2	Homo sapiens (human)
presynaptic membrane	Ephrin type-B receptor 2	Homo sapiens (human)
neuronal cell body	Ephrin type-B receptor 2	Homo sapiens (human)
dendritic spine	Ephrin type-B receptor 2	Homo sapiens (human)
postsynaptic membrane	Ephrin type-B receptor 2	Homo sapiens (human)
hippocampal mossy fiber to CA3 synapse	Ephrin type-B receptor 2	Homo sapiens (human)
postsynapse	Ephrin type-B receptor 2	Homo sapiens (human)
glutamatergic synapse	Ephrin type-B receptor 2	Homo sapiens (human)
plasma membrane	Ephrin type-B receptor 2	Homo sapiens (human)
dendrite	Ephrin type-B receptor 2	Homo sapiens (human)
nucleus	C-terminal-binding protein 1	Homo sapiens (human)
nucleoplasm	C-terminal-binding protein 1	Homo sapiens (human)
presynaptic active zone cytoplasmic component	C-terminal-binding protein 1	Homo sapiens (human)
glutamatergic synapse	C-terminal-binding protein 1	Homo sapiens (human)
GABA-ergic synapse	C-terminal-binding protein 1	Homo sapiens (human)
transcription repressor complex	C-terminal-binding protein 1	Homo sapiens (human)
nucleus	C-terminal-binding protein 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (38)

Assay ID	Title	Year	Journal	Article
AID548156	Anticancer activity against human T24 cells assessed as inhibition of cell proliferation at 10 ug/ml after 10 days using crystal violet staining by clonogenic assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1187960	Cytotoxicity against african green monkey Vero cells by MTT assay	2014	Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17	2-Phenylaminonaphthoquinones and related compounds: synthesis, trypanocidal and cytotoxic activities.
AID548155	Lipophilicity, log P of the compound	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548150	Cytotoxicity against human DU145 cells after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1677754	Cytotoxicity against human MCF-7 assessed as reduction in cell viability incubated for 72 hrs by MTT assay	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Novel 2-amino-1,4-naphthoquinone hybrids: Design, synthesis, cytotoxicity evaluation and in silico studies.
AID548164	Anticancer activity against human T24 cells assessed as decreased in intracellular ATP level after 6 hrs by ATPlite assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1186373	Inhibition of phosphatidylserine-stimulated GTPase activity of sheep brain Dynamin 1 expressed in Sf21 cells assessed as inhibition of orthophosphate release from GTP by malachite green method	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Development of quinone analogues as dynamin GTPase inhibitors.
AID548162	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 10 ug/ml after 24 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548163	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 100 ug/ml after 24 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1677757	Cytotoxicity against human HEK-293 assessed as reduction in cell viability incubated for 72 hrs by MTT assay	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Novel 2-amino-1,4-naphthoquinone hybrids: Design, synthesis, cytotoxicity evaluation and in silico studies.
AID548151	Cytotoxicity against mouse BALB/3T3 cells after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID240825	Inhibition of EPH receptor B2 using ELISA	2005	Journal of medicinal chemistry, May-05, Volume: 48, Issue:9	Frontal affinity chromatography with MS detection of EphB2 tyrosine kinase receptor. 2. Identification of small-molecule inhibitors via coupling with virtual screening.
AID548158	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 1 ug/ml after 6 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548159	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 10 ug/ml after 6 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548152	Selectivity index, ratio of EC50 for mouse BALB/3T3 cells to EC50 for human DU145 cells	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548161	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 1 ug/ml after 24 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548153	Selectivity index, ratio of EC50 for mouse BALB/3T3 cells to EC50 for human MCF7 cells	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548157	Anticancer activity against human T24 cells assessed as decreased in intracellular ATP level at 100 ug/ml after 6 hrs by ATPlite assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548148	Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID548154	Selectivity index, ratio of EC50 for mouse BALB/3T3 cells to EC50 for human T24 cells	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1677756	Cytotoxicity against human U937 assessed as reduction in cell viability incubated for 72 hrs by MTT assay	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Novel 2-amino-1,4-naphthoquinone hybrids: Design, synthesis, cytotoxicity evaluation and in silico studies.
AID1677755	Cytotoxicity against human HL-60 assessed as reduction in cell viability incubated for 72 hrs by MTT assay	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Novel 2-amino-1,4-naphthoquinone hybrids: Design, synthesis, cytotoxicity evaluation and in silico studies.
AID548149	Cytotoxicity against human T24 cells after 48 hrs by MTT assay	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID1187958	Trypanocidal activity against epimastigote stage of Trypanosoma cruzi infected in african green monkey Vero cells assessed as cell viability after 24 hrs by MTT assay	2014	Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17	2-Phenylaminonaphthoquinones and related compounds: synthesis, trypanocidal and cytotoxic activities.
AID548160	Induction of apoptosis in human T24 cells assessed as increase of caspase-3-mediated DEVDase activity at 100 ug/ml after 6 hrs	2010	European journal of medicinal chemistry, Dec, Volume: 45, Issue:12	Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	2 (16.67)	29.6817
2010's	8 (66.67)	24.3611
2020's	2 (16.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	12 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
ag-1296 6,7-dimethoxy-3-phenylquinoxaline: ATP-competitive inhibitor of receptor kinase	2.02	1	quinoxaline derivative
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	7.13	1	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
pd 153035 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline: structure given in first source. PD-153035 : A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7.	2.02	1	aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist
ag 1879 3-(4-chlorophenyl)-1-(1,1-dimethylethyl)-1H-pyrazolo(3,4-d)pyrimidin-4-amine: Fyn kinase inhibitor	2.02	1	aromatic amine; monochlorobenzenes; pyrazolopyrimidine	beta-adrenergic antagonist; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.05	1	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	2.08	1	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
whi p180 [no description available]	2.02	1
sb 203580 [no description available]	2.02	1	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
Src Inhibitor-1 Src Inhibitor-1 : A member of the class of quinazolines that is quinazoline which is substituted at position 4 by a p-phenoxyanilino group and at positions 6 and 7 by methoxy groups. It is a potent, competitive dual site (both the ATP- and peptide-binding) Src kinase inhibitor. Src Inhibitor-1 is one of the 'gold standards' for Src kinase inhibition that has been shown to use PP1 or PP2 in parallel with Src-I1 to inhbit Src family kinases.	2.02	1	aromatic ether; polyether; quinazolines; secondary amino compound	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.51	2
cb676475 CB676475: structure in first source	2.02	1	quinazolines
nifurtimox Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.	2.1	1	nitrofuran antibiotic
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.51	2	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.05	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.05	1
Bladder Cancer [description not available]	2.08	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.08	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.08	1
Disease Exacerbation [description not available]	2.13	1
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.13	1

2-(4-hydroxyanilino)-1,4-naphthoquinone

Description

Cross-References

Synonyms (19)

Research Excerpts

Compound-Compound Interactions

Protein Targets (43)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (82)

Molecular Functions (21)

Ceullar Components (22)

Bioassays (38)

Research

Studies (12)

Market Indicators

Research Demand Index: 11.90

Study Types

2-(4-hydroxyanilino)-1,4-naphthoquinone

Description

Cross-References

Synonyms (19)

Research Excerpts

Compound-Compound Interactions

Protein Targets (43)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (82)

Molecular Functions (21)

Ceullar Components (22)

Bioassays (38)

Research

Studies (12)

Market Indicators

Research Demand Index: 11.90

Study Types

Related Drugs (13)

Related Conditions (7)