linarin profile

linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Linaria	genus	A plant genus of the family Plantaginaceae. Members contain linarin (also called acaciin).[MeSH]	Plantaginaceae	A plant family of order Lamiales. The Plantago genus is best known. Lesser known members include Hippuris, Littorella and Callitriche.[MeSH]
Linaria japonica	species	[no description available]	Plantaginaceae	A plant family of order Lamiales. The Plantago genus is best known. Lesser known members include Hippuris, Littorella and Callitriche.[MeSH]

ID Source	ID
PubMed CID	5317025
CHEMBL ID	509502
SCHEMBL ID	1155704
MeSH ID	M0051999

Synonym
acacetin 7-o-rutinoside
buddleoside
hbh2i685iu ,
einecs 207-547-6
acacetin 7-o-alpha-l-rhamnopyranosyl-(1->6)-beta-d-glucopyranoside
acacetin-7-o-(6''-o-rhamnose)-beta-d-glucoside
acacetin-7-o-rutinoside
5-hydroxy-4'-methoxyflavone-7-o-rutinoside
linarine
unii-hbh2i685iu
linarigenin glycoside
acacetin-7-o-.eta-d-rutinoside
7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-4h-benzopyran-4-one
linarin
480-36-4
CHEMBL509502
acaciin
acacetin 7-rutinoside
5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
S9290
AKOS015896769
SCHEMBL1155704
mfcd00151178
linarin [mi]
acacetin-.beta.-rutinoside
5,7-dihydroxy-4-methoxyflavone-d-glucosido-l-rhamnoside
7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-
linarigenin-glucoside
Q-100519
YFVGIJBUXMQFOF-PJOVQGMDSA-N
4h-1-benzopyran-4-one, 7-[[6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-5-hydroxy-2-(4-methoxyphenyl)-
DTXSID40197382
AC-8009
HY-N0528
7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-5-hydroxy-4'-methoxyflavone
5-hydroxy-2-(4-methoxyphenyl)-7-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one
buddleoside,(s)
5-hydroxy-2-(4-methoxyphenyl)-7-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one
Q1775837
HMS3887E11
5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4h-chromen-7-yl 6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside
STL564542
CCG-270166
buddleoside;linarine
CS-0009062
linarin;buddleoside
bdbm50524083
7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-5-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one

Excerpt	Reference	Relevance
"Linarin is a flavonoid glycoside, and it can promote osteoblastogenesis."	( Linarin Protects against Cadmium-Induced Osteoporosis Via Reducing Oxidative Stress and Inflammation and Altering RANK/RANKL/OPG Pathway. Cheng, R; Cui, Y; Du, B; Fang, J; Liu, J; Wang, X; Yang, Y; Zhang, P, 2022)	2.89
"Linarin is a natural flavonoid glycoside that is widely available in Compositae, Chrysanthemum indicum and Dendrocalamus and processes protective effects in several animal models."	( Inhibiting TLR4 signaling by linarin for preventing inflammatory response in osteoarthritis. Chen, Y; Liu, H; Pan, X; Qi, W; Shang, P; Sun, S; Xu, X; Yan, Z; Zhan, J, 2021)	1.63

Excerpt	Reference	Relevance
"Linarin (LIN) has been widely used for different diseases."	( Linarin Protects the Kidney against Ischemia/Reperfusion Injury via the Inhibition of Bioactive ETS2/IL-12. Bin, Z; Caixia, C; Chengyu, Y; Congjuan, L; Hong, L; Long, Z; Xuefei, S; Yan, X, 2021)	2.79

Excerpt	Reference	Relevance
"Linarin could also inhibit acetylcholinesterase activity induced by Aβ(25-35) in PC12 cells."	( Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death. Fan, P; Lou, H; Perez, RG, 2011)	1.39
"Linarin was found to inhibit NO production in the LPS-activated RAW 264.7 cells."	( The effect of linarin on LPS-induced cytokine production and nitric oxide inhibition in murine macrophages cell line RAW264.7. Ha, NJ; Han, S; Kim, K; Lee, CK; Lee, S; Sung, KH; Yim, D, 2002)	1.4

Excerpt	Reference	Relevance
"Linarin treatment reversed the lethality induced by GalN/LPS."	( Protective effect of linarin against D-galactosamine and lipopolysaccharide-induced fulminant hepatic failure. Cho, HI; Kim, JS; Kim, SJ; Kim, YH; Kwak, JH; Lee, SK; Lee, SM; Park, JH, 2014)	1.44
"The linarin-treated total lymphocytes exhibited cytotoxicity in a dose dependent manner between 20 microg/ml and 40 microg/ml."	( The effect of linarin on LPS-induced cytokine production and nitric oxide inhibition in murine macrophages cell line RAW264.7. Ha, NJ; Han, S; Kim, K; Lee, CK; Lee, S; Sung, KH; Yim, D, 2002)	1.16

Excerpt	Reference	Relevance
" The developed assay method was applied to the pharmacokinetic study in rats after a single intramuscular administration of 713 µg/kg linarin."	( Rapid LC-MS/MS determination and pharmacokinetic application of linarin in rat plasma. Lin, L; Liu, H; Yan, C, 2013)	0.83
" Then, the pharmacokinetic profiles of linarin in rats after oral administration of linarin (50 mg/kg) alone and in combination with piperine (20 mg/kg) were determined using a validated LC-MS/MS method."	( Effects of piperine on the intestinal permeability and pharmacokinetics of linarin in rats. Di, X; Feng, X; Liu, Y; Wang, X, 2014)	0.9
" The validated method was successfully applied to the pharmacokinetic study of linarin in rat plasma after intramuscular administration of monomeric compound and traditional Chinese medicinal preparation - Yejuhua injection."	( Determination and pharmacokinetics of linarin in rat plasma after intramuscular administration of linarin solution and Yejuhua injection by HPLC. Bi, K; Jia, Y; Li, X; Mao, X; Xu, X; Zhao, X, 2015)	0.92
" The developed method was successfully applied to a pharmacokinetic study of linarin, naringenin and formononetin in rats after oral administration of Bushen Guchi Pill."	( Simultaneous determination of linarin, naringenin and formononetin in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Bushen Guchi Pill. Dong, L; Guo, P; Wang, C; Wei, J; Yan, W; Zhang, Z, 2015)	0.93
" The validated method has been successfully applied to pharmacokinetic and tissue distribution study of linarin."	( A rapid and sensitive LC-MS/MS method for the determination of linarin in small-volume rat plasma and tissue samples and its application to pharmacokinetic and tissue distribution study. Di, X; Feng, X; Liu, Y; Wang, X, 2016)	0.89

Excerpt	Reference	Relevance
"To study the relaxation effect of buddleoside combined with luteolin on aortic rings in SD rats and its mechanism."	( [Relaxation effect of buddleoside combined with luteolin on isolated vessels in vivo and its mechanism]. Chen, B; Chen, SH; Liang, KL; Lv, GY; Su, J; Yang, Y, 2017)	0.46

Excerpt	Reference	Relevance
"Although linarin possesses diverse pharmacological activities, its poor oral bioavailability has been a concern for further development."	( Effects of piperine on the intestinal permeability and pharmacokinetics of linarin in rats. Di, X; Feng, X; Liu, Y; Wang, X, 2014)	1.05

Excerpt	Relevance	Reference
" BLIN stimulated total anti-DHAV-1 antibody secretion in ducklings at the dosage of 4 mg per duckling, but did not stimulate IL-2 and IFN-γ secretion significantly."	( Anti-DHAV-1 reproduction and immuno-regulatory effects of a flavonoid prescription on duck virus hepatitis. Chen, Y; Hu, Y; Liu, J; Wang, D; Wang, Y; Wu, Y; Yang, J; Yao, F; Zeng, L, 2017)	0.46

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Tyrosinase	Homo sapiens (human)	IC50 (µMol)	50.0000	0.0230	4.4593	10.0000	AID1594853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
melanin biosynthetic process from tyrosine	Tyrosinase	Homo sapiens (human)
eye pigment biosynthetic process	Tyrosinase	Homo sapiens (human)
visual perception	Tyrosinase	Homo sapiens (human)
cell population proliferation	Tyrosinase	Homo sapiens (human)
response to UV	Tyrosinase	Homo sapiens (human)
response to blue light	Tyrosinase	Homo sapiens (human)
response to vitamin D	Tyrosinase	Homo sapiens (human)
melanin biosynthetic process	Tyrosinase	Homo sapiens (human)
thymus development	Tyrosinase	Homo sapiens (human)
response to cAMP	Tyrosinase	Homo sapiens (human)
pigmentation	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
tyrosinase activity	Tyrosinase	Homo sapiens (human)
copper ion binding	Tyrosinase	Homo sapiens (human)
protein binding	Tyrosinase	Homo sapiens (human)
identical protein binding	Tyrosinase	Homo sapiens (human)
protein homodimerization activity	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Tyrosinase	Homo sapiens (human)
lysosome	Tyrosinase	Homo sapiens (human)
Golgi-associated vesicle	Tyrosinase	Homo sapiens (human)
melanosome membrane	Tyrosinase	Homo sapiens (human)
melanosome	Tyrosinase	Homo sapiens (human)
intracellular membrane-bounded organelle	Tyrosinase	Homo sapiens (human)
perinuclear region of cytoplasm	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay ID	Title	Year	Journal	Article
AID734905	Lipophilicity, log P of the compound	2013	Journal of natural products, Jan-25, Volume: 76, Issue:1	Enhancement of the water solubility of flavone glycosides by disruption of molecular planarity of the aglycone moiety.
AID598189	Antiproliferative activity against PDGF-BB-induced rat VSMC proliferation at 10 uM after 24 hrs by WST1 (CCK-8) assay	2011	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11	A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
AID598193	Antiproliferative activity against PDGF-BB-induced rat VSMC proliferation after 24 hrs by WST1 (CCK-8) assay	2011	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11	A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
AID613351	Cytoprotective activity in amyloid beta-induced apoptosis in rat PC12 cells administered 1 hr prior to amyloid beta challenge measured after 24 hrs by using Annexin V/PI staining based flow cytometric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1625179	Antimicrobial activity against Candida albicans ATCC 10231 after 48 hrs by microbroth dilution method	2019	Journal of natural products, 03-22, Volume: 82, Issue:3	Antifungal Phenylpropanoid Glycosides from Lippia rubella.
AID613358	Neuroprotective activity in amyloid beta-induced rat PC12 cells assessed as increase of Bcl-2 expression at 0.1 to 10 uM administered 1 hrs prior to amyloid beta challenge measured after 24 hrs by Western blotting	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1162204	Cytotoxicity against mouse RAW264.7 cells at 0.01 to 100 uM after 24 hrs by MTT assay	2014	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18	New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production.
AID613357	Increase in GSK3 beta phosphorylation at Ser9 in amyloid beta-induced rat PC12 cells at 0.1 to 10 uM administered 1 hrs prior to amyloid beta challenge measured after 24 hrs by Western blotting pretreated with PI3K inhibitor LY294002 before compound addit	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID598192	Cytotoxicity against PDGF-BB-induced rat VSMC at 50 uM	2011	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11	A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
AID1594855	Antimicrobial activity against bacteria	2019	Journal of natural products, 06-28, Volume: 82, Issue:6	Isolation of Sesquiterpene-Amino Acid Conjugates, Onopornoids A-D, and a Flavonoid Glucoside from Onopordum alexandrinum.
AID613353	Inhibition of amyloid beta-induced apoptosis in rat PC12 cells assessed as decrease in caspase-3 dependent cleavage of Ac-DEVD-pNA administered 1 hr prior to amyloid beta challenge measured after 24 hrs by spectrophotometric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1594854	Antimicrobial activity against Leishmania	2019	Journal of natural products, 06-28, Volume: 82, Issue:6	Isolation of Sesquiterpene-Amino Acid Conjugates, Onopornoids A-D, and a Flavonoid Glucoside from Onopordum alexandrinum.
AID1625182	Antifungal activity against Cryptococcus neoformans ATCC 24067 after 48 hrs by micro broth dilution method	2019	Journal of natural products, 03-22, Volume: 82, Issue:3	Antifungal Phenylpropanoid Glycosides from Lippia rubella.
AID338974	Inhibition of cow milk xanthine oxidase at 50 ug/mL
AID613346	Cytoprotective activity in amyloid beta-induced apoptosis in rat PC12 cells at 10 uM administered 1 hr prior to amyloid beta challenge measured after 24 hrs by using Annexin V/PI staining based flow cytometric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1775659	Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	2021	Journal of natural products, 03-26, Volume: 84, Issue:3	Sesquiterpenoids from
AID613350	Cytoprotective activity in amyloid beta-induced apoptosis in rat PC12 cells at 1 uM administered 1 hr prior to amyloid beta challenge measured after 24 hrs by using Annexin V/PI staining based flow cytometric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID613356	Increase in GSK3 beta phosphorylation at Ser9 in amyloid beta-induced rat PC12 cells at 0.1 to 10 uM administered 1 hrs prior to amyloid beta challenge measured after 24 hrs by Western blotting	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID613355	Induction of PIK3-mediated Akt phosphorylation in amyloid beta-induced rat PC12 cells at 10 uM, treated 1 hrs prior to amyloid beta challenge measured after 24 hrs by Western blotting in presence of PI3K inhibitor LY294002 before compound addition	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1698073	Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cells assessed as increase in cell viability after 24 hrs by EZ-Cytox assay
AID1625180	Antifungal activity against Candida parapsilosis ATCC 22019 after 24 hrs by micro broth dilution method	2019	Journal of natural products, 03-22, Volume: 82, Issue:3	Antifungal Phenylpropanoid Glycosides from Lippia rubella.
AID598191	Antiproliferative activity against PDGF-BB-induced rat VSMC proliferation at 50 uM after 24 hrs by WST1 (CCK-8) assay	2011	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11	A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
AID1625181	Antifungal activity against Cryptococcus neoformans isolate T1444 after 48 hrs by micro broth dilution method	2019	Journal of natural products, 03-22, Volume: 82, Issue:3	Antifungal Phenylpropanoid Glycosides from Lippia rubella.
AID613354	Neuroprotective effect against amyloid beta-induced apoptosis in rat PC12 cells assessed as upregulation of PI3K-mediated Akt phosphorylation administered 1 hr prior to amyloid beta challenge measured after 24 hrs by Western blotting	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID613347	Neuroprotective activity in amyloid beta-induced cytotoxicity in rat PC12 cells assessed as cell viability pretreated 1 hrs prior to amyloid beta challenge measured after 24 hrs by MTT assay	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID1594853	Inhibition of tyrosinase (unknown origin)	2019	Journal of natural products, 06-28, Volume: 82, Issue:6	Isolation of Sesquiterpene-Amino Acid Conjugates, Onopornoids A-D, and a Flavonoid Glucoside from Onopordum alexandrinum.
AID613348	Inhibition of AChE activity in amyloid beta25-35-induced rat PC12 cells at 0.1 to 10 uM, 1 hrs prior to induction after 24 hrs by Ellman assay	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID734906	Aqueous solubility of the compound in water after 2 days by HPLC analysis	2013	Journal of natural products, Jan-25, Volume: 76, Issue:1	Enhancement of the water solubility of flavone glycosides by disruption of molecular planarity of the aglycone moiety.
AID1162203	Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells pre-incubated for 2 hrs before LPS stimulation for 24 hrs by Griess assay method	2014	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18	New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production.
AID598190	Antiproliferative activity against PDGF-BB-induced rat VSMC proliferation at 30 uM after 24 hrs by WST1 (CCK-8) assay	2011	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11	A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
AID1775658	Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 24 hrs by Griess reagent based assay	2021	Journal of natural products, 03-26, Volume: 84, Issue:3	Sesquiterpenoids from
AID613352	Inhibition of amyloid beta-induced mitochondrial dysfunction in rat PC12 cells at 0.1 to 10 uM administered 1 hr prior to amyloid beta challenge measured after 24 hrs using JC1 fluorescent dye based flow cytometeric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID613359	Neuroprotective effect against amyloid beta-induced rat PC12 cells assessed as increase of Bcl-2 expression at 0.1 to 10 uM administered 1 hrs prior to amyloid beta challenge measured after 24 hrs by Western blotting pretreated with PI3K inhibitor LY29400	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
AID613349	Cytoprotective activity in amyloid beta-induced apoptosis in rat PC12 cells at 0.1 uM administered 1 hr prior to amyloid beta challenge measured after 24 hrs by using Annexin V/PI staining based flow cytometric analysis	2011	Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13	Neuroprotective effects of linarin through activation of the PI3K/Akt pathway in amyloid-β-induced neuronal cell death.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (2.33)	18.7374
1990's	4 (4.65)	18.2507
2000's	17 (19.77)	29.6817
2010's	50 (58.14)	24.3611
2020's	13 (15.12)	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	90 (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
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.03	1	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.13	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
histamine [no description available]	2.15	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.07	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.57	2	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	1.99	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	2.02	1	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.08	1	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.06	1	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
aldosterone [no description available]	2.08	1	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	7.17	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.47	2	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.25	1
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2	1	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.07	1	flavanones
oleanolic acid [no description available]	2.03	1	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	8.45	7	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.07	1	flavones	metabolite; nematicide
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.06	1	dialdehyde	biomarker
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	7.41	1	cadmium molecular entity; zinc group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.54	2	D-galactosamine; primary amino compound	toxin
rhamnose [no description available]	2.02	1	L-rhamnose
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.97	4	D-glucopyranose	epitope; mouse metabolite
baicalin [no description available]	2.86	3	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
1-octacosanol 1-octacosanol: RN given refers to parent cpd. octacosan-1-ol : An ultra-long-chain primary fatty alcohol that is octacosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group.	2.03	1	fatty alcohol 28:0; ultra-long-chain primary fatty alcohol	plant metabolite
hesperetin [no description available]	2.31	1	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
lupenone lupenone: structure in first source	2.03	1	triterpenoid	metabolite
loliolide loliolide: RN given refers to (6S-cis)-isomer	2.31	1	benzofurans	metabolite
arctiin arctiin: from fruits of Arctium lappa L; RN given refers to (3R-trans)-isomer; RN for cpd without isomeric designation not avail 12/92	2.21	1	glycoside; lignan
taraxasterol taraxasterol: from Cirsium segetum. taraxasterol : A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3.	2.03	1	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory agent; metabolite
buddlejasaponin iv buddlejasaponin IV: a triterpenoid saponin from the roots of Bupleurum rigidum; structure in first source	2.06	1
rhodioloside [no description available]	2.06	1	glycoside
cirsimarin cirsimarin: a flavone glycoside from Microtea debilis; structure given in first source	2.17	1	flavonoids; glycoside
nevadensin nevadensin: from Lysionotus pauceflora Maxim; RN & N1 from 9th CI. nevadensin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 8 and 4' and hydroxy groups at positions 5 and 7 respectively.	2.1	1	dihydroxyflavone; trimethoxyflavone	plant metabolite
pectolinarin pectolinarin: antihemorrhagic principle from Chinese plant Cirsium japonicum DC.. pectolinarin : A disaccharide derivative that consists of pectolinarigenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.67	3	dimethoxyflavone; disaccharide derivative; glycosyloxyflavone; monohydroxyflavanone; rutinoside	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; plant metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.08	1	amino acid zwitterion; angiotensin II	human metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	7.11	1	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
notoginsenoside r1 notoginsenoside R1 : A ginsenoside found in Panax notoginseng that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy groups at positions 6 and 20 have been converted to the corresponding beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside and beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.	2.86	3	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antioxidant; apoptosis inducer; neuroprotective agent; phytoestrogen; plant metabolite
naringin [no description available]	7.47	2	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.44	2	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
glycosides [no description available]	5.75	78
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	7.1	1	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
sesquiterpenes [no description available]	2.44	2
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.46	2	caffeic acid	geroprotector; mouse metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	3.48	7	cinnamate ester; tannin	food component; plant metabolite
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.02	1	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.73	3
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.86	3
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.41	1	long-chain fatty acid
quercetin [no description available]	2.44	2	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.31	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
formononetin [no description available]	7.11	1	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	3.68	9	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	8.67	9	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.77	10	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
luteolin-7-glucuronide luteolin-7-glucuronide: isolated from Lycopus europaeus L.; active against pregnant mare serum gonadotropin. luteolin 7-O-beta-D-glucosiduronic acid : A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position.	2.31	1	glycosyloxyflavone; luteolin O-glucuronoside; monosaccharide derivative; trihydroxyflavone	metabolite
luteolin-7-glucoside luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.57	2	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	2.47	2	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.82	3	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.21	1	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.07	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.21	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
diosmetin [no description available]	3.01	4	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
diosmin [no description available]	8.15	5	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.03	1	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
robustaflavone robustaflavone: bis-apigenin coupled at 6 and 3' positions; a potential non-nucleoside anti-hepatitis B agent;. robustaflavone : A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-6 of the chromene ring. Isolated from Thuja orientalis and Rhus succedanea it exhibits antioxidant, cytotoxic and anti-hepatitis B activity.	2.02	1	biflavonoid; hydroxyflavone; ring assembly	anti-HBV agent; antineoplastic agent; antioxidant; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	2.11	1	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
forsythiaside forsythiaside: RN given refers to (E)-isomer; structure given in first source; from the unripe fruit of Forsythia suspensa (qinglianquiao)	2.21	1	hydroxycinnamic acid
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	8.01	4	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	2.08	1	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.08	1	thromboxanes B	human metabolite; mouse metabolite
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	1.99	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.4	2	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
icariin [no description available]	2.86	3	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
apigenin-7-o-beta-d-glucuronide [no description available]	2.31	1	flavonoids; glucosiduronic acid
tilianin tilianin: from several medicinal plants including Agastache rugosa and Dracocephalum moldavia	8.08	4
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.07	1	carbon group element atom; elemental lead; metal atom	neurotoxin
valerenic acid valerenic acid: a saturated oplopanone type indene from Valeriana officinalis. valerenic acid : A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.	2.44	2	carbobicyclic compound; monocarboxylic acid; sesquiterpenoid	GABA modulator; plant metabolite; sedative; volatile oil component
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.21	1	hydroxycinnamic acid
apigenin-7-o-rutinoside [no description available]	2.77	3
Phenylethyl beta-D-glucopyranoside [no description available]	2.06	1	glycoside
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.05	1
fortunellin fortunellin: from Mentha piperita; structure in first source	2.07	1
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.52	2
Pechueloic acid [no description available]	2.1	1	sesquiterpenoid
piperidines Piperidines: A family of hexahydropyridines.	2.1	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.08	1	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.66	2
Age-Related Osteoporosis [description not available]	2.83	3
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.	2.66	2
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	7.83	3
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.41	1
Acute Ischemic Stroke [description not available]	2.41	1
Cerebral Ischemia [description not available]	2.41	1
Injury, Ischemia-Reperfusion [description not available]	2.82	3
Ischemic Stroke Stroke due to BRAIN ISCHEMIA resulting in interruption or reduction of blood flow to a part of the brain. When obstruction is due to a BLOOD CLOT formed within in a cerebral blood vessel it is a thrombotic stroke. When obstruction is formed elsewhere and moved to block a cerebral blood vessel (see CEREBRAL EMBOLISM) it is referred to as embolic stroke. Wake-up stroke refers to ischemic stroke occurring during sleep while cryptogenic stroke refers to ischemic stroke of unknown origin.	2.41	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.41	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.82	3
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.41	1
Bone Loss, Osteoclastic [description not available]	2.76	2
Bone Loss, Perimenopausal [description not available]	2.6	1
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	2.6	1
Acute Liver Injury, Drug-Induced [description not available]	2.59	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.08	4
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.59	2
Acute Kidney Failure [description not available]	2.31	1
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.31	1
Arthritis, Degenerative [description not available]	2.31	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	7.31	1
2019 Novel Coronavirus Disease [description not available]	2.31	1
Injury, Myocardial Reperfusion [description not available]	2.15	1
Benign Neoplasms, Brain [description not available]	2.15	1
Glial Cell Tumors [description not available]	2.55	2
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.15	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.55	2
Blood Pressure, High [description not available]	2.52	2
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.52	2
Lung Injury, Acute [description not available]	2.17	1
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	7.17	1
Abnormal Movements [description not available]	2.21	1
Acute Confusional Senile Dementia [description not available]	2.21	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.21	1
Caliciviridae Infections Virus diseases caused by CALICIVIRIDAE. They include HEPATITIS E; VESICULAR EXANTHEMA OF SWINE; acute respiratory infections in felines, rabbit hemorrhagic disease, and some cases of gastroenteritis in humans.	2.21	1
Acute Hepatic Failure [description not available]	2.1	1
Liver Failure, Acute A form of rapid-onset LIVER FAILURE, also known as fulminant hepatic failure, caused by severe liver injury or massive loss of HEPATOCYTES. It is characterized by sudden development of liver dysfunction and JAUNDICE. Acute liver failure may progress to exhibit cerebral dysfunction even HEPATIC COMA depending on the etiology that includes hepatic ISCHEMIA, drug toxicity, malignant infiltration, and viral hepatitis such as post-transfusion HEPATITIS B and HEPATITIS C.	2.1	1
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	2.1	1
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	2.15	1
Hepatitis, Animal INFLAMMATION of the LIVER in non-human animals.	2.15	1
Bacterial Pneumonia [description not available]	2.06	1
Chlamydia pneumoniae Infections [description not available]	2.06	1
Pneumonia, Bacterial Inflammation of the lung parenchyma that is caused by bacterial infections.	2.06	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.46	2
Absence Seizure [description not available]	2.08	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.08	1
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	2.08	1
Cancer of Prostate [description not available]	2.02	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.02	1
Pyrexia [description not available]	1.99	1
Ache [description not available]	2.4	2
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	1.99	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.4	2
Anasarca [description not available]	1.99	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.99	1

linarin

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Synonyms (49)

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Overview

Effects

Actions

Treatment

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Protein Targets (1)

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Bioassays (34)

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Studies (86)

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Research Demand Index: 33.25

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linarin

Description

Related Flora

Cross-References

Synonyms (49)

Research Excerpts

Overview

Effects

Actions

Treatment

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Protein Targets (1)

Inhibition Measurements

Biological Processes (11)

Molecular Functions (5)

Ceullar Components (7)

Bioassays (34)

Research

Studies (86)

Market Indicators

Research Demand Index: 33.25

Study Types

Related Drugs (87)

Related Conditions (56)