Page last updated: 2024-12-08

5-amino-8-hydroxyquinoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-amino-8-hydroxyquinoline: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID416002
CHEMBL ID449298
SCHEMBL ID688655
MeSH IDM0521011

Synonyms (34)

Synonym
13207-66-4
AC-7829
BB 0221209
AS-0308-225 ,
5-aminoquinolin-8-ol
5-amino-quinolin-8-ol
AKOS000111586
CHEMBL449298
FT-0659557
A806359
5-amino-8-hydroxyquinoline
BRD-K00624318-300-01-3
STK737829
8-quinolinol, 5-amino-
SCHEMBL688655
5-amino-8-quinolinol
5-amino-8-quinolinol #
AM85404
bdbm32142
cid_416002
5-azanylquinolin-8-ol
DTXSID20328975
J-516727
5-amino-8-hydroxyquinoline hclsalt
CS-W001023
GS-5740
mfcd00185837
CCG-321501
5-aminoquinoline-8-ol
5-aminooxin
SY045850
SB67953
HY-W001023
PD119507
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
90-kda heat shock protein beta HSP90 beta, partialHomo sapiens (human)IC50 (µMol)22.29140.17369.803229.2701AID712; AID754
heat shock protein HSP 90-alpha isoform 2Homo sapiens (human)IC50 (µMol)22.29140.17369.803229.2701AID712; AID754
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)2.05000.00022.45859.9600AID1640021
Indoleamine 2,3-dioxygenase 1Homo sapiens (human)IC50 (µMol)3.00000.05373.075710.0000AID443993
Catechol O-methyltransferaseRattus norvegicus (Norway rat)IC50 (µMol)29.51210.00222.81277.0795AID1149251
Proteasome subunit beta type-5Homo sapiens (human)IC50 (µMol)0.60000.00050.939410.0000AID1301250; AID1301251; AID1301252; AID1301253; AID1301254; AID1301255; AID1301256; AID1301257
Indoleamine 2,3-dioxygenase 1Mus musculus (house mouse)IC50 (µMol)1.00000.00601.625110.0000AID443995
Tryptophan 2,3-dioxygenaseMus musculus (house mouse)IC50 (µMol)5.00001.00002.48675.0000AID443997
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
regulation of activated T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell tolerance inductionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of chronic inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of type 2 immune responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
female pregnancyIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic process to kynurenineIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
response to lipopolysaccharideIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of interleukin-10 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of interleukin-12 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
multicellular organismal response to stressIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
kynurenic acid biosynthetic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
swimming behaviorIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
'de novo' NAD biosynthetic process from tryptophanIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
proteolysisProteasome subunit beta type-5Homo sapiens (human)
response to oxidative stressProteasome subunit beta type-5Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (19)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
electron transfer activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
heme bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
indoleamine 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
metal ion bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
threonine-type endopeptidase activityProteasome subunit beta type-5Homo sapiens (human)
protein bindingProteasome subunit beta type-5Homo sapiens (human)
peptidase activityProteasome subunit beta type-5Homo sapiens (human)
endopeptidase activityProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cytosolIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
smooth muscle contractile fiberIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
stereocilium bundleIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
cytoplasmIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
nucleusProteasome subunit beta type-5Homo sapiens (human)
cytoplasmProteasome subunit beta type-5Homo sapiens (human)
proteasome complexProteasome subunit beta type-5Homo sapiens (human)
nucleusProteasome subunit beta type-5Homo sapiens (human)
nucleoplasmProteasome subunit beta type-5Homo sapiens (human)
centrosomeProteasome subunit beta type-5Homo sapiens (human)
cytosolProteasome subunit beta type-5Homo sapiens (human)
extracellular exosomeProteasome subunit beta type-5Homo sapiens (human)
proteasome core complexProteasome subunit beta type-5Homo sapiens (human)
proteasome core complex, beta-subunit complexProteasome subunit beta type-5Homo sapiens (human)
cytosolProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID443993Inhibition of human recombinant IDO expressed in Escherichia coli BL21 AI2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID443997Inhibition of mouse recombinant TDO expressed in mouse P815B cells assessed as blockade of tryptophan degradation by HPLC2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID568480Antifungal activity against Aspergillus niger KCTC 1231 after 2 days by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID444000Cytotoxicity against mouse P815B cells expressing mouse recombinant TDO by MTT assay2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID1244907Cytotoxicity against human HL60 cells after 48 hrs by MTT assay2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID568481Antifungal activity against Aspergillus flavus KCCM 11899 after 2 days by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID568477Antifungal activity against Candida tropicalis KCCM 50662 after 1 day by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID568478Antifungal activity against Candida krusei KCCM 11655 after 1 day by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID1244912Selectivity ratio of IC50 for human HL7702 cells to IC50 for human SMMC7721 cells2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID1301256Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human MDAY-D2 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectrop2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID1301254Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human NB4 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectrophoto2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID412143Antifungal activity against Candida tropicalis KCCM 50662 after 1 day2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles.
AID1244911Cytotoxicity against human HL7702 cells after 48 hrs by MTT assay2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID1244909Cytotoxicity against human SW480 cells after 48 hrs by MTT assay2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID1301251Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human KMH11 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectropho2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID1301257Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human K562 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectrophot2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID412146Antifungal activity against Cryptococcus neoformans KCCM 50564 after 1 day2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles.
AID1301250Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human UTMC2 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectropho2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID1301253Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human OCI-AML2 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectro2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID568479Antifungal activity against Cryptococcus neoformans KCCM 50564 after 2 days by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID443996Inhibition of human recombinant IDO expressed in HEK293 cells assessed as blockade of tryptophan degradation by HPLC2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID443999Cytotoxicity against HEK293 cells expressing human recombinant IDO by MTT assay2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID443995Inhibition of mouse recombinant IDO expressed in mouse P815B cells assessed as blockade of tryptophan degradation by HPLC2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
AID1301255Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human KG1A cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectrophot2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID412144Antifungal activity against Candida albicans KCCM 50235 after 1 day2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles.
AID1149251Inhibition of Sprague-Dawley rat liver COMT after 10 mins using 0.05 uCi [14CH3]-SAM as substrate1976Journal of medicinal chemistry, Apr, Volume: 19, Issue:4
Catechol O-methyltransferase. 8. Structure-activity relationships for inhibtion by 8-hydroxyquinolines.
AID1244910Cytotoxicity against human SMMC7721 cells after 48 hrs by MTT assay2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID568476Antifungal activity against Candida albicans KCCM 50235 after 1 day by twofold broth dilution method2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Synthesis and antifungal activity of furo[2,3-f]quinolin-5-ols.
AID412145Antifungal activity against Candida krusei KCCM 11655 after 1 day2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles.
AID1301252Inhibition of human 20S proteasome chymotryptic-like activity using Suc-LLVY-AMC as substrate expressed in human KMS18 cells assessed as free 7-amino-4-methylcoumarin release preincubated for 22 hrs followed by substrate addition by fluorescent spectropho2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Substituted quinolines as noncovalent proteasome inhibitors.
AID1244908Cytotoxicity against human A549 cells after 48 hrs by MTT assay2015European journal of medicinal chemistry, Sep-18, Volume: 102Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID412147Antifungal activity against Aspergillus niger KCTC 1231 after 2 days2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles.
AID443998Cytotoxicity against mouse P815B cells expressing mouse recombinant IDO by MTT assay2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Rational design of indoleamine 2,3-dioxygenase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (9.09)18.7374
1990's0 (0.00)18.2507
2000's2 (18.18)29.6817
2010's7 (63.64)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.28

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.28 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]