Page last updated: 2024-11-12

ks370g

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Description

KS370G: antihyperglycemic; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11391937
CHEMBL ID67498
SCHEMBL ID18385862
MeSH IDM0553516

Synonyms (31)

Synonym
CHEMBL67498
caffeic acid phenethyl amide
2-propenamide, 3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)-
105955-01-9
bdbm50429750
103188-47-2
SCHEMBL18385862
ks 370g, >=98% (hplc)
3-(3,4-dihydroxyphenyl)-n-phenethylpropenamide
3-(3,4-dihydroxyphenyl)-n-phenethylpropenamide, (e)-
n-trans-caffeoyl phenethylamine
2-propenamide, 3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)-, (2e)-
BTT4WXT3J9 ,
(2e)-3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)-2-propenamide
caffeol-.beta.-phenethylamine
3-(3,4-dihydroxy-phenyl)-n-phenethyl-acrylamide
ks370g
ks 370g
(e)-3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)prop-2-enamide
(e)-3-(3,4-dihydroxyphenyl)-n-phenethylpropenamide
ks 370 g
ks-370-g
(2e)-3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)prop-2-enamide
caffeol-beta-phenethylamine
unii-btt4wxt3j9
(2e)-3-(3,4-dihydroxyphenyl)-n-(2-phenylethyl)acrylamide
DTXSID101030308
Z1625092019
AKOS040745953
CS-0063781
HY-114683

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with KS370G also induced heme oxygenase (HO)-1 and suppressors of cytokine signaling (SOCS)-3 expression in the microglia."( Anti-neuroinflammatory effect of a novel caffeamide derivative, KS370G, in microglial cells.
Huang, BR; Huang, SS; Kuo, YH; Lin, HY; Liu, YS; Lu, DY; Yeh, WL, 2013
)
0.97

Pharmacokinetics

ExcerptReferenceRelevance
" This method was used to determine the pharmacokinetic profiles of CAPA and CAPE in male Sprague-Dawley rats following intravenous bolus administration of 5, 10 and 20 mg/kg of CAPA and 20 mg/kg of CAPE."( Development and validation of an LCMS method to determine the pharmacokinetic profiles of caffeic acid phenethyl amide and caffeic acid phenethyl ester in male Sprague-Dawley rats.
Bowman, PD; Kerwin, SM; Stavchansky, S; Yang, J, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Interstitial collagenaseHomo sapiens (human)IC50 (µMol)3.30130.00020.850210.0000AID735584
72 kDa type IV collagenaseHomo sapiens (human)IC50 (µMol)0.00820.00001.284810.0000AID735583
Matrix metalloproteinase-9Homo sapiens (human)IC50 (µMol)0.00730.00000.705310.0000AID735582
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (65)

Processvia Protein(s)Taxonomy
proteolysisInterstitial collagenaseHomo sapiens (human)
protein metabolic processInterstitial collagenaseHomo sapiens (human)
extracellular matrix disassemblyInterstitial collagenaseHomo sapiens (human)
collagen catabolic processInterstitial collagenaseHomo sapiens (human)
positive regulation of protein-containing complex assemblyInterstitial collagenaseHomo sapiens (human)
cellular response to UV-AInterstitial collagenaseHomo sapiens (human)
extracellular matrix organizationInterstitial collagenaseHomo sapiens (human)
angiogenesis72 kDa type IV collagenaseHomo sapiens (human)
ovarian follicle development72 kDa type IV collagenaseHomo sapiens (human)
ovulation from ovarian follicle72 kDa type IV collagenaseHomo sapiens (human)
luteinization72 kDa type IV collagenaseHomo sapiens (human)
blood vessel maturation72 kDa type IV collagenaseHomo sapiens (human)
intramembranous ossification72 kDa type IV collagenaseHomo sapiens (human)
proteolysis72 kDa type IV collagenaseHomo sapiens (human)
negative regulation of cell adhesion72 kDa type IV collagenaseHomo sapiens (human)
heart development72 kDa type IV collagenaseHomo sapiens (human)
embryo implantation72 kDa type IV collagenaseHomo sapiens (human)
parturition72 kDa type IV collagenaseHomo sapiens (human)
response to xenobiotic stimulus72 kDa type IV collagenaseHomo sapiens (human)
response to mechanical stimulus72 kDa type IV collagenaseHomo sapiens (human)
peripheral nervous system axon regeneration72 kDa type IV collagenaseHomo sapiens (human)
response to activity72 kDa type IV collagenaseHomo sapiens (human)
protein metabolic process72 kDa type IV collagenaseHomo sapiens (human)
extracellular matrix disassembly72 kDa type IV collagenaseHomo sapiens (human)
protein catabolic process72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of cell migration72 kDa type IV collagenaseHomo sapiens (human)
collagen catabolic process72 kDa type IV collagenaseHomo sapiens (human)
response to retinoic acid72 kDa type IV collagenaseHomo sapiens (human)
cellular response to reactive oxygen species72 kDa type IV collagenaseHomo sapiens (human)
response to nicotine72 kDa type IV collagenaseHomo sapiens (human)
endodermal cell differentiation72 kDa type IV collagenaseHomo sapiens (human)
response to hydrogen peroxide72 kDa type IV collagenaseHomo sapiens (human)
response to estrogen72 kDa type IV collagenaseHomo sapiens (human)
negative regulation of vasoconstriction72 kDa type IV collagenaseHomo sapiens (human)
ephrin receptor signaling pathway72 kDa type IV collagenaseHomo sapiens (human)
macrophage chemotaxis72 kDa type IV collagenaseHomo sapiens (human)
response to electrical stimulus72 kDa type IV collagenaseHomo sapiens (human)
response to hyperoxia72 kDa type IV collagenaseHomo sapiens (human)
face morphogenesis72 kDa type IV collagenaseHomo sapiens (human)
bone trabecula formation72 kDa type IV collagenaseHomo sapiens (human)
prostate gland epithelium morphogenesis72 kDa type IV collagenaseHomo sapiens (human)
cellular response to amino acid stimulus72 kDa type IV collagenaseHomo sapiens (human)
cellular response to interleukin-172 kDa type IV collagenaseHomo sapiens (human)
cellular response to estradiol stimulus72 kDa type IV collagenaseHomo sapiens (human)
cellular response to UV-A72 kDa type IV collagenaseHomo sapiens (human)
cellular response to fluid shear stress72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of oxidative stress-induced neuron intrinsic apoptotic signaling pathway72 kDa type IV collagenaseHomo sapiens (human)
response to amyloid-beta72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation72 kDa type IV collagenaseHomo sapiens (human)
extracellular matrix organization72 kDa type IV collagenaseHomo sapiens (human)
response to hypoxia72 kDa type IV collagenaseHomo sapiens (human)
tissue remodeling72 kDa type IV collagenaseHomo sapiens (human)
skeletal system developmentMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of protein phosphorylationMatrix metalloproteinase-9Homo sapiens (human)
proteolysisMatrix metalloproteinase-9Homo sapiens (human)
apoptotic processMatrix metalloproteinase-9Homo sapiens (human)
embryo implantationMatrix metalloproteinase-9Homo sapiens (human)
cell migrationMatrix metalloproteinase-9Homo sapiens (human)
extracellular matrix disassemblyMatrix metalloproteinase-9Homo sapiens (human)
macrophage differentiationMatrix metalloproteinase-9Homo sapiens (human)
collagen catabolic processMatrix metalloproteinase-9Homo sapiens (human)
cellular response to reactive oxygen speciesMatrix metalloproteinase-9Homo sapiens (human)
endodermal cell differentiationMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of apoptotic processMatrix metalloproteinase-9Homo sapiens (human)
negative regulation of apoptotic processMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of DNA bindingMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwayMatrix metalloproteinase-9Homo sapiens (human)
ephrin receptor signaling pathwayMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of keratinocyte migrationMatrix metalloproteinase-9Homo sapiens (human)
cellular response to lipopolysaccharideMatrix metalloproteinase-9Homo sapiens (human)
cellular response to cadmium ionMatrix metalloproteinase-9Homo sapiens (human)
cellular response to UV-AMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondriaMatrix metalloproteinase-9Homo sapiens (human)
regulation of neuroinflammatory responseMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of receptor bindingMatrix metalloproteinase-9Homo sapiens (human)
response to amyloid-betaMatrix metalloproteinase-9Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferationMatrix metalloproteinase-9Homo sapiens (human)
negative regulation of epithelial cell differentiation involved in kidney developmentMatrix metalloproteinase-9Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathwayMatrix metalloproteinase-9Homo sapiens (human)
negative regulation of cation channel activityMatrix metalloproteinase-9Homo sapiens (human)
negative regulation of cysteine-type endopeptidase activity involved in apoptotic signaling pathwayMatrix metalloproteinase-9Homo sapiens (human)
extracellular matrix organizationMatrix metalloproteinase-9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
endopeptidase activityInterstitial collagenaseHomo sapiens (human)
metalloendopeptidase activityInterstitial collagenaseHomo sapiens (human)
serine-type endopeptidase activityInterstitial collagenaseHomo sapiens (human)
peptidase activityInterstitial collagenaseHomo sapiens (human)
zinc ion bindingInterstitial collagenaseHomo sapiens (human)
fibronectin binding72 kDa type IV collagenaseHomo sapiens (human)
endopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
metalloendopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
serine-type endopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
protein binding72 kDa type IV collagenaseHomo sapiens (human)
metallopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
zinc ion binding72 kDa type IV collagenaseHomo sapiens (human)
endopeptidase activityMatrix metalloproteinase-9Homo sapiens (human)
metalloendopeptidase activityMatrix metalloproteinase-9Homo sapiens (human)
serine-type endopeptidase activityMatrix metalloproteinase-9Homo sapiens (human)
protein bindingMatrix metalloproteinase-9Homo sapiens (human)
collagen bindingMatrix metalloproteinase-9Homo sapiens (human)
peptidase activityMatrix metalloproteinase-9Homo sapiens (human)
metallopeptidase activityMatrix metalloproteinase-9Homo sapiens (human)
zinc ion bindingMatrix metalloproteinase-9Homo sapiens (human)
identical protein bindingMatrix metalloproteinase-9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionInterstitial collagenaseHomo sapiens (human)
extracellular matrixInterstitial collagenaseHomo sapiens (human)
extracellular spaceInterstitial collagenaseHomo sapiens (human)
collagen-containing extracellular matrix72 kDa type IV collagenaseHomo sapiens (human)
extracellular region72 kDa type IV collagenaseHomo sapiens (human)
extracellular space72 kDa type IV collagenaseHomo sapiens (human)
nucleus72 kDa type IV collagenaseHomo sapiens (human)
mitochondrion72 kDa type IV collagenaseHomo sapiens (human)
plasma membrane72 kDa type IV collagenaseHomo sapiens (human)
sarcomere72 kDa type IV collagenaseHomo sapiens (human)
collagen-containing extracellular matrix72 kDa type IV collagenaseHomo sapiens (human)
extracellular space72 kDa type IV collagenaseHomo sapiens (human)
extracellular regionMatrix metalloproteinase-9Homo sapiens (human)
extracellular spaceMatrix metalloproteinase-9Homo sapiens (human)
collagen-containing extracellular matrixMatrix metalloproteinase-9Homo sapiens (human)
extracellular exosomeMatrix metalloproteinase-9Homo sapiens (human)
tertiary granule lumenMatrix metalloproteinase-9Homo sapiens (human)
ficolin-1-rich granule lumenMatrix metalloproteinase-9Homo sapiens (human)
extracellular spaceMatrix metalloproteinase-9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1718310Growth inhibition of human KMM-1 cells at 1 to 10 uM after 48 hrs by PrestoBlue cell viability assay2020Journal of natural products, 12-24, Volume: 83, Issue:12
Antimyeloma Potential of Caffeic Acid Phenethyl Ester and Its Analogues through Sp1 Mediated Downregulation of IKZF1-IRF4-MYC Axis.
AID735580Selectivity ratio of IC50 for human recombinant MMP1 to IC50 for human recombinant MMP92013Bioorganic & medicinal chemistry letters, Mar-01, Volume: 23, Issue:5
Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
AID263688Inhibitory activity against tyrosinase at 100uM2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase.
AID780240Antiproliferative activity against human LNCAP cells after 72 hrs in presence of DHT2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID735581Selectivity ratio of IC50 for human recombinant MMP1 to IC50 for human recombinant MMP22013Bioorganic & medicinal chemistry letters, Mar-01, Volume: 23, Issue:5
Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
AID125798Evaluated for the antioxidant property by measuring the inhibition of microsomal lipid peroxidation2001Bioorganic & medicinal chemistry letters, Jan-22, Volume: 11, Issue:2
Synthesis and evaluation of caffeic acid amides as antioxidants.
AID1718330Down regulation of cyclin D3 expression in human KMM-1 cells at 5 to 50 uM after 48 hrs by immunoblotting analysis2020Journal of natural products, 12-24, Volume: 83, Issue:12
Antimyeloma Potential of Caffeic Acid Phenethyl Ester and Its Analogues through Sp1 Mediated Downregulation of IKZF1-IRF4-MYC Axis.
AID735583Inhibition of human recombinant MMP2 using succinylated gelatin as substrate incubated for 30 mins prior to substrate addition measured after 60 mins2013Bioorganic & medicinal chemistry letters, Mar-01, Volume: 23, Issue:5
Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
AID780242Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 24 hrs by WST-1 assay2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID735584Inhibition of human recombinant MMP1 using succinylated gelatin as substrate incubated for 30 mins prior to substrate addition measured after 60 mins2013Bioorganic & medicinal chemistry letters, Mar-01, Volume: 23, Issue:5
Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
AID735582Inhibition of human recombinant MMP9 using succinylated gelatin as substrate incubated for 30 mins prior to substrate addition measured after 60 mins2013Bioorganic & medicinal chemistry letters, Mar-01, Volume: 23, Issue:5
Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.
AID780232Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.
AID1542227Inhibition of synthetic AcPHF6 peptide aggregation in pH 7.4 phosphate buffer assessed as reduction in fluorescence intensity at 50 uM and measured every minute over 2 hrs with 5 secs shaking prior to each reading by ThT fluorescence assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.
AID1524671Covalent inhibition of purified Sporosarcinia pasteurii urease by phenol red based method
AID514357Cytoprotective activity against H2O2-induced oxidative stress in HUVEC cells after 18 hrs by Cell-Titer Blue assay2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: comparison of cytoprotective effects to caffeic acid phenethyl ester (CAPE).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (11.11)29.6817
2010's14 (77.78)24.3611
2020's2 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.02

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.02 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

All Compounds (24.57)

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%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]