Page last updated: 2024-10-15

nbi 31772

Description

NBI 31772: an insulin-like growth factor-binding protein ligand; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

NBI-31772 : An isoquinoline substituted by 3,4-dihydroxybenzoyl, carboxy, hydroxy, and hydroxy groups at positions 1, 3, 6, and 7, respectively. It is a potent inhibitor of insulin-like growth factor-1 binding protein (IGFBP). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135543997
CHEMBL ID292700
CHEBI ID195417
SCHEMBL ID6014808
MeSH IDM0401633

Synonyms (27)

Synonym
nbi-31772
nbi 31772
CHEMBL292700 ,
1-(3,4-dihydroxy-benzoyl)-6,7-dihydroxy-isoquinoline-3-carboxylic acid
bdbm50106431
1-(3,4-dihydroxybenzoyl)-6,7-dihydroxyisoquinoline-3-carboxylic acid
6,7-dihydroxy-1-(3,4-dihydroxybenzoyl)isoquinoline-3-carboxylic acid
374620-70-9
nbi31772
1-(3',4'-dihydroxybenzoyl)-6,7-dihydroxyisoquinoline-3-carboxylic acid
CHEBI:195417
1-(3,4-dihydroxybenzoyl)-6,7-dihydroxy-3-isoquinolinecarboxylic acid
nbi-31772 hydrate
3-isoquinolinecarboxylic acid, 1-(3,4-dihydroxybenzoyl)-6,7-dihydroxy-
SCHEMBL6014808
AKOS025147334
DTXSID80741040
1-[(3,4-dioxocyclohexa-1,5-dien-1-yl)(hydroxy)methylidene]-6,7-dihydroxy-1,2-dihydroisoquinoline-3-carboxylic acid
unii-7dyh3xnp6h
7DYH3XNP6H ,
4-(3-(dihydroxymethylidene)-6,7-dihydroxy-2h-isoquinoline-1-carbonyl)cyclohexa-3,5-diene-1,2-dione
MS-25209
ZPA62070
EX-A6162
[1-(3',4'-dihydroxybenzoyl)-6,7-dihydroxyisoquinoline-3-carboxylic acid]
CS-0032990
HY-110135

Bioavailability

ExcerptReference
" Whereas IGF-I peptide variants, which bind to IGFBPs but not the IGF-I receptor, have been shown to be potent IGF/IGFBP inhibitors, small molecule nonpeptide IGF/IGFBP inhibitors have the potential advantages of oral bioavailability and flexible dosing regimen."( Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
Chen, C; Ling, N; Liu, XJ; Lu, ZX; Xie, Q; Zhu, YF, 2001
)
"The insulin-like growth factor-binding protein 4 (IGFBP-4), which exists in many different tissues and biological fluids, modulates insulin-like growth factor 1 (IGF-1) bioavailability in part by competitive sequestration and prevention of interaction with cell membrane IGF-1 receptors."( Development of a scintillation proximity assay for human insulin-like growth factor-binding protein 4 compatible with inhibitor high-throughput screening.
Khawaja, XZ, 2007
)

Dosage Studied

ExcerptReference
" Whereas IGF-I peptide variants, which bind to IGFBPs but not the IGF-I receptor, have been shown to be potent IGF/IGFBP inhibitors, small molecule nonpeptide IGF/IGFBP inhibitors have the potential advantages of oral bioavailability and flexible dosing regimen."( Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
Chen, C; Ling, N; Liu, XJ; Lu, ZX; Xie, Q; Zhu, YF, 2001
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
insulin-like growth factor-binding protein inhibitorAny inhibitor that acts on insulin-like growth factor-binding proteins.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
benzenediols
tetrolA polyol that contains 4 hydroxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Insulin-like growth factor-binding protein 1Homo sapiens (human)Ki0.00510.00510.00510.0051AID93211
Insulin-like growth factor-binding protein 3Homo sapiens (human)Ki0.00560.00560.00560.0056AID93214; AID93215
Insulin-like growth factor-binding protein 2Homo sapiens (human)Ki0.00210.00210.00210.0021AID93212
Insulin-like growth factor-binding protein 4Homo sapiens (human)Ki0.00100.00100.00100.0010AID93216
Insulin-like growth factor-binding protein 6Homo sapiens (human)Ki0.02360.02360.02360.0236AID93355
Insulin-like growth factor-binding protein 5Homo sapiens (human)Ki0.00540.00520.00540.0056AID93353; AID93354
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
signal transductionInsulin-like growth factor-binding protein 1Homo sapiens (human)
insulin receptor signaling pathwayInsulin-like growth factor-binding protein 1Homo sapiens (human)
response to organic cyclic compoundInsulin-like growth factor-binding protein 1Homo sapiens (human)
positive regulation of cell growthInsulin-like growth factor-binding protein 1Homo sapiens (human)
tissue regenerationInsulin-like growth factor-binding protein 1Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayInsulin-like growth factor-binding protein 1Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 1Homo sapiens (human)
negative regulation of protein phosphorylationInsulin-like growth factor-binding protein 3Homo sapiens (human)
protein phosphorylationInsulin-like growth factor-binding protein 3Homo sapiens (human)
negative regulation of cell population proliferationInsulin-like growth factor-binding protein 3Homo sapiens (human)
MAPK cascadeInsulin-like growth factor-binding protein 3Homo sapiens (human)
regulation of cell growthInsulin-like growth factor-binding protein 3Homo sapiens (human)
osteoblast differentiationInsulin-like growth factor-binding protein 3Homo sapiens (human)
apoptotic processInsulin-like growth factor-binding protein 3Homo sapiens (human)
negative regulation of signal transductionInsulin-like growth factor-binding protein 3Homo sapiens (human)
regulation of glucose metabolic processInsulin-like growth factor-binding protein 3Homo sapiens (human)
negative regulation of smooth muscle cell migrationInsulin-like growth factor-binding protein 3Homo sapiens (human)
positive regulation of apoptotic processInsulin-like growth factor-binding protein 3Homo sapiens (human)
positive regulation of MAPK cascadeInsulin-like growth factor-binding protein 3Homo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 3Homo sapiens (human)
type B pancreatic cell proliferationInsulin-like growth factor-binding protein 3Homo sapiens (human)
positive regulation of myoblast differentiationInsulin-like growth factor-binding protein 3Homo sapiens (human)
negative regulation of smooth muscle cell proliferationInsulin-like growth factor-binding protein 3Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 3Homo sapiens (human)
female pregnancyInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to nutrientInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to xenobiotic stimulusInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to mechanical stimulusInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to estradiolInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to retinoic acidInsulin-like growth factor-binding protein 2Homo sapiens (human)
cellular response to hormone stimulusInsulin-like growth factor-binding protein 2Homo sapiens (human)
positive regulation of activated T cell proliferationInsulin-like growth factor-binding protein 2Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to estrogenInsulin-like growth factor-binding protein 2Homo sapiens (human)
response to glucocorticoidInsulin-like growth factor-binding protein 2Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayInsulin-like growth factor-binding protein 2Homo sapiens (human)
MAPK cascadeInsulin-like growth factor-binding protein 4Homo sapiens (human)
regulation of cell growthInsulin-like growth factor-binding protein 4Homo sapiens (human)
signal transductionInsulin-like growth factor-binding protein 4Homo sapiens (human)
regulation of glucose metabolic processInsulin-like growth factor-binding protein 4Homo sapiens (human)
response to organic cyclic compoundInsulin-like growth factor-binding protein 4Homo sapiens (human)
positive regulation of MAPK cascadeInsulin-like growth factor-binding protein 4Homo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 4Homo sapiens (human)
type B pancreatic cell proliferationInsulin-like growth factor-binding protein 4Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayInsulin-like growth factor-binding protein 4Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 4Homo sapiens (human)
signal transductionInsulin-like growth factor-binding protein 6Homo sapiens (human)
negative regulation of cell population proliferationInsulin-like growth factor-binding protein 6Homo sapiens (human)
cell migrationInsulin-like growth factor-binding protein 6Homo sapiens (human)
positive regulation of stress-activated MAPK cascadeInsulin-like growth factor-binding protein 6Homo sapiens (human)
positive regulation of MAPK cascadeInsulin-like growth factor-binding protein 6Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayInsulin-like growth factor-binding protein 6Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 6Homo sapiens (human)
regulation of cell growthInsulin-like growth factor-binding protein 5Homo sapiens (human)
osteoblast differentiationInsulin-like growth factor-binding protein 5Homo sapiens (human)
signal transductionInsulin-like growth factor-binding protein 5Homo sapiens (human)
female pregnancyInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of smooth muscle cell migrationInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of translationInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of cell migrationInsulin-like growth factor-binding protein 5Homo sapiens (human)
hair follicle morphogenesisInsulin-like growth factor-binding protein 5Homo sapiens (human)
intracellular signal transductionInsulin-like growth factor-binding protein 5Homo sapiens (human)
glucose homeostasisInsulin-like growth factor-binding protein 5Homo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 5Homo sapiens (human)
type B pancreatic cell proliferationInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of osteoblast differentiationInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of growthInsulin-like growth factor-binding protein 5Homo sapiens (human)
insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 5Homo sapiens (human)
lung alveolus developmentInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of smooth muscle cell proliferationInsulin-like growth factor-binding protein 5Homo sapiens (human)
striated muscle cell differentiationInsulin-like growth factor-binding protein 5Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionInsulin-like growth factor-binding protein 5Homo sapiens (human)
mammary gland involutionInsulin-like growth factor-binding protein 5Homo sapiens (human)
response to growth hormoneInsulin-like growth factor-binding protein 5Homo sapiens (human)
cellular response to cAMPInsulin-like growth factor-binding protein 5Homo sapiens (human)
cellular response to organic cyclic compoundInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of muscle tissue developmentInsulin-like growth factor-binding protein 5Homo sapiens (human)
negative regulation of skeletal muscle hypertrophyInsulin-like growth factor-binding protein 5Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferationInsulin-like growth factor-binding protein 5Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell migrationInsulin-like growth factor-binding protein 5Homo sapiens (human)
regulation of insulin-like growth factor receptor signaling pathwayInsulin-like growth factor-binding protein 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
signaling receptor bindingInsulin-like growth factor-binding protein 1Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 1Homo sapiens (human)
insulin-like growth factor bindingInsulin-like growth factor-binding protein 1Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 1Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 1Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
insulin-like growth factor bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
protein tyrosine phosphatase activator activityInsulin-like growth factor-binding protein 3Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
metal ion bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
fibronectin bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 3Homo sapiens (human)
signaling receptor bindingInsulin-like growth factor-binding protein 2Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 2Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 2Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 2Homo sapiens (human)
signaling receptor bindingInsulin-like growth factor-binding protein 4Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 4Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 4Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 4Homo sapiens (human)
signaling receptor bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
identical protein bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
fibronectin bindingInsulin-like growth factor-binding protein 6Homo sapiens (human)
protein bindingInsulin-like growth factor-binding protein 5Homo sapiens (human)
insulin-like growth factor I bindingInsulin-like growth factor-binding protein 5Homo sapiens (human)
fibronectin bindingInsulin-like growth factor-binding protein 5Homo sapiens (human)
insulin-like growth factor II bindingInsulin-like growth factor-binding protein 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
extracellular regionInsulin-like growth factor-binding protein 1Homo sapiens (human)
endoplasmic reticulum lumenInsulin-like growth factor-binding protein 1Homo sapiens (human)
Golgi apparatusInsulin-like growth factor-binding protein 1Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 1Homo sapiens (human)
extracellular regionInsulin-like growth factor-binding protein 3Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 3Homo sapiens (human)
nucleusInsulin-like growth factor-binding protein 3Homo sapiens (human)
endoplasmic reticulum lumenInsulin-like growth factor-binding protein 3Homo sapiens (human)
insulin-like growth factor binding protein complexInsulin-like growth factor-binding protein 3Homo sapiens (human)
insulin-like growth factor ternary complexInsulin-like growth factor-binding protein 3Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 3Homo sapiens (human)
extracellular regionInsulin-like growth factor-binding protein 2Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 2Homo sapiens (human)
apical plasma membraneInsulin-like growth factor-binding protein 2Homo sapiens (human)
extracellular exosomeInsulin-like growth factor-binding protein 2Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 2Homo sapiens (human)
extracellular regionInsulin-like growth factor-binding protein 4Homo sapiens (human)
endoplasmic reticulum lumenInsulin-like growth factor-binding protein 4Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 4Homo sapiens (human)
extracellular regionInsulin-like growth factor-binding protein 6Homo sapiens (human)
insulin-like growth factor binary complexInsulin-like growth factor-binding protein 6Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 6Homo sapiens (human)
extracellular regionInsulin-like growth factor-binding protein 5Homo sapiens (human)
endoplasmic reticulum lumenInsulin-like growth factor-binding protein 5Homo sapiens (human)
insulin-like growth factor binding protein complexInsulin-like growth factor-binding protein 5Homo sapiens (human)
insulin-like growth factor ternary complexInsulin-like growth factor-binding protein 5Homo sapiens (human)
extracellular spaceInsulin-like growth factor-binding protein 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID93211The compound was tested for binding affinity against insulin-like growth factor binding protein 12001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID21899Calculated partition coefficient (clogP)2003Bioorganic & medicinal chemistry letters, Jun-02, Volume: 13, Issue:11
6,7-dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain.
AID93212The compound was tested for binding affinity against insulin-like growth factor binding protein 22001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID93216The compound was tested for binding affinity against Insulin-like growth factor binding protein 42001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID93354The compound was tested for binding affinity against Insulin-like growth factor binding protein 52001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID93355The compound was tested for binding affinity against Insulin-like growth factor binding protein 62001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID93214Ability to displace Insulin-Like Growth Factor (IGF-I) from its binding to human insulin-like growth factor binding protein 3 (hIGFBP-3)2003Bioorganic & medicinal chemistry letters, Jun-02, Volume: 13, Issue:11
6,7-dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain.
AID93215Inhibitory activity against Insulin-like growth factor binding protein 32001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
AID93353Ability of compound to displace Insulin-Like Growth Factor (IGF-I) from its binding to Insulin-like growth factor binding protein 5 (IGFBP-5)2003Bioorganic & medicinal chemistry letters, Jun-02, Volume: 13, Issue:11
Quinoline-carboxylic acids are potent inhibitors that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's11 (78.57)29.6817
2010's2 (14.29)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]