Compounds > glaucocalyxin a

Page last updated: 2024-11-12

glaucocalyxin a

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Description

glaucocalyxin A: chemical constituent of Rabdosia japonica var. glaucocalyx [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Rabdosia	genus	[no description available]	Lamiaceae	The mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
Rabdosia japonica	species	[no description available]	Lamiaceae	The mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID Source	ID
PubMed CID	10471963
CHEMBL ID	549359
MeSH ID	M0155336

Synonyms (13)

Synonym
glaucocalyxin a
CHEMBL549359
79498-31-0
AC-34443
7alpha,14beta-dihydroxy-ent-kaur-16-ene-3,5-dione
CS-0018634
HY-N2112
AKOS037514678
(1r,2r,4s,9r,10s,13s,16r)-2,16-dihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-6,15-dione
wangzaozin b
leukamenin f
MS-25010
bdbm50552053

Research Excerpts

Overview

Glaucocalyxin A (GLA) is an alkaloid derived from a Chinese medicinal plant that exhibits anti-inflammatory, anti-tumor and neuroprotective properties. The compound has been found to ameliorate myocardial I/R injury in mice.

Excerpt	Reference	Relevance
"Glaucocalyxin A (GLA) is a bioactive natural compound with anti-inflammatory activity. "	( Glaucocalyxin A Attenuates IL-1 Li, Y; Wu, H; Zhang, Y; Zhu, W, 2022)	3.61
"Glaucocalyxin A (GLA) is a bioactive ent-kauranoid diterpenoid derived from the herbal medicine, Rabdosia japonica var. "	( Glaucocalyxin A alleviates LPS-mediated septic shock and inflammation via inhibiting NLRP3 inflammasome activation. Ai, Y; Bai, Z; Chen, Y; Hou, X; Li, H; Li, R; Shi, W; Wang, C; Wang, Z; Xiao, X; Xu, G; Zhan, X, 2020)	3.44
"Glaucocalyxin A (GLA) is a biologically active ent-kauranoid diterpenoid that has been found to ameliorate myocardial I/R injury in mice."	( Glaucocalyxin A Protects H9c2 Cells Against Hypoxia/Reoxygenation-Induced Injury Through the Activation of Akt/Nrf2/HO-1 Pathway. Dang, X; Lv, J; Niu, Z; Pan, L; Pei, H; Peng, Z; Wang, H; Zhang, R, )	2.3
"Glaucocalyxin A (GLA) is an alkaloid derived from a Chinese medicinal plant that exhibits anti-inflammatory, anti-tumor and neuroprotective properties."	( Glaucocalyxin A suppresses inflammatory responses and induces apoptosis in TNF-a-induced human rheumatoid arthritis via modulation of the STAT3 pathway. Li, W; Ma, K; Wang, F; Yang, Y; Zhang, C, 2021)	2.79
"Glaucocalyxin A (GLA) is a diterpenoid component isolated from Rabdosia japonica var."	( Glaucocalyxin A induces apoptosis and autophagy in tongue squamous cell carcinoma cells by regulating ROS. Jiang, Q; Qiu, J; Shi, F; Xue, D, 2021)	2.79
"Glaucocalyxin A (GLA) is a biologically active ent-kauranoid diterpenoid isolated from Rabdosia japonica var. "	( Glaucocalyxin A Attenuates the Activation of Hepatic Stellate Cells Through the TGF-β1/Smad Signaling Pathway. Dong, Z; Gao, Q; Guo, H, 2018)	3.37
"Glaucocalyxin A (GLA) is a natural ent-Kaurane diterpenoid that possesses cardioprotective effect. "	( Glaucocalyxin A attenuates angiotensin II-induced cardiac fibrosis in cardiac fibroblasts. Su, Q; Zhang, Y, 2018)	3.37
"Glaucocalyxin A (GLA), is a diterpenoid extracted from Hara and has been studied for decades for its diverse bioactivities. "	( Preparation, optimization of the inclusion complex of glaucocalyxin A with sulfobutylether-β-cyclodextrin and antitumor study. Chen, G; Ren, L; Wang, J, 2019)	2.21
"Glaucocalyxin A is a natural ent-Kaurane diterpenoid. "	( Glaucocalyxin A: a review. Jin, Y; Liu, X; Wu, X; Xiang, Z, 2014)	3.29
"Glaucocalyxin A (GLA) is a biologically active ent-kauranoid diterpenoid isolated from Rabdosia japonica var. "	( Glaucocalyxin A induces apoptosis in human leukemia HL-60 cells through mitochondria-mediated death pathway. Gao, LW; Wang, B; Wang, JW; Yang, WH; Zhang, J, 2011)	3.25
"Glaucocalyxin A (Gla A) is a new diterpenoid isolated from ethereal extract of the leaves of Rabdosia japonica (Burm f) Hara var glaucocalyx (Maxim) Hara (Labiatae) collected in Northeastern China. "	( Effects of glaucocalyxin A on aggregation and cAMP levels of rabbit platelets in vitro. Long, K; Zhang, B, 1993)	2.12
"Glaucocalyxin A is a new diterpenoid isolated from the ethereal extract of the leaves of Rabdosia japonica (Burm f) Hara var glaucocalyx (Maxim) Hara (Labiatae) collected in the northeastern China. "	( Inhibition by glaucocalyxin A of aggregation of rabbit platelets induced by ADP, arachidonic acid and platelet-activating factor, and inhibition of [3H]-PAF binding. Bin, Z; Kun, L, 1992)	2.09

Pharmacokinetics

Excerpt	Reference	Relevance
" A pharmacokinetic analysis of glaucocalyxin A after intravenous administration in rats revealed that glaucocalyxin A followed a two-compartment open model."	( Pharmacokinetic analysis of glaucocalyxin A in rat plasma by liquid-liquid extraction and HPLC. Cao, L; Chen, Z; Li, Y; Shen Li, Y; Sun, J, 2009)	0.93

Bioavailability

Excerpt	Reference	Relevance
"The purpose of this study was to develop a new formulation to enhance the bioavailability simultaneously with controlled release of glaucocalyxin A (GLA)."	( Controlled release of glaucocalyxin - a self-nanoemulsifying system from osmotic pump tablets with enhanced bioavailability. Guoguang, C; Lili, R; Pingkai, O; Yanfei, M, 2017)	0.66
"In this study, controlled release of GLA was achieved by the osmotic release strategy taking advantage of the bioavailability enhancing capacity of self-nanoemulsifying drug delivery systems (SNEDDS)."	( Controlled release of glaucocalyxin - a self-nanoemulsifying system from osmotic pump tablets with enhanced bioavailability. Guoguang, C; Lili, R; Pingkai, O; Yanfei, M, 2017)	0.46
"It was concluded that simultaneous controlling on GLA release and enhanced bioavailability had been achieved by a combination of osmotic pump tablet and SNEDDS."	( Controlled release of glaucocalyxin - a self-nanoemulsifying system from osmotic pump tablets with enhanced bioavailability. Guoguang, C; Lili, R; Pingkai, O; Yanfei, M, 2017)	0.46
" However, GLA presents poor solubility in water and low bioavailability through oral administration which has hindered its application in the clinic."	( Preparation, optimization of the inclusion complex of glaucocalyxin A with sulfobutylether-β-cyclodextrin and antitumor study. Chen, G; Ren, L; Wang, J, 2019)	0.76

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Platelet glycoprotein VI	Homo sapiens (human)	IC50 (µMol)	0.0115	0.0020	1.5588	4.0000	AID1692274; AID1692275
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Process	via Protein(s)	Taxonomy
positive regulation of platelet aggregation	Platelet glycoprotein VI	Homo sapiens (human)
enzyme-linked receptor protein signaling pathway	Platelet glycoprotein VI	Homo sapiens (human)
platelet activation	Platelet glycoprotein VI	Homo sapiens (human)
collagen-activated tyrosine kinase receptor signaling pathway	Platelet glycoprotein VI	Homo sapiens (human)
collagen-activated signaling pathway	Platelet glycoprotein VI	Homo sapiens (human)
platelet aggregation	Platelet glycoprotein VI	Homo sapiens (human)
immune response-regulating signaling pathway	Platelet glycoprotein VI	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Process	via Protein(s)	Taxonomy
transmembrane signaling receptor activity	Platelet glycoprotein VI	Homo sapiens (human)
protein binding	Platelet glycoprotein VI	Homo sapiens (human)
collagen binding	Platelet glycoprotein VI	Homo sapiens (human)
signaling receptor activity	Platelet glycoprotein VI	Homo sapiens (human)
collagen receptor activity	Platelet glycoprotein VI	Homo sapiens (human)
protein tyrosine kinase binding	Platelet glycoprotein VI	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Process	via Protein(s)	Taxonomy
membrane raft	Platelet glycoprotein VI	Homo sapiens (human)
plasma membrane	Platelet glycoprotein VI	Homo sapiens (human)
cell surface	Platelet glycoprotein VI	Homo sapiens (human)
extracellular exosome	Platelet glycoprotein VI	Homo sapiens (human)
tetraspanin-enriched microdomain	Platelet glycoprotein VI	Homo sapiens (human)
plasma membrane	Platelet glycoprotein VI	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay ID	Title	Year	Journal	Article
AID1161858	Induction of apoptosis in human KB cells assessed as early apoptotic cells level at 10 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 7.08%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161839	Antiproliferative activity against human HL7702 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID426932	Cytotoxicity against human SH-SY5Y cells after 48 hrs by SRB method	2009	Journal of natural products, Jun, Volume: 72, Issue:6	ent-Kaurane diterpenoids from Isodon pharicus.
AID1692275	Antagonist activity at GP6 in human platelet assessed as reduction in CRP-induced platelet-aggregation preincubated for 10 mins followed by collagen stimulation by aggregometry	2020	Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21	Progress toward a Glycoprotein VI Modulator for the Treatment of Thrombosis.
AID426933	Cytotoxicity against human PC3 cells after 48 hrs by SRB method	2009	Journal of natural products, Jun, Volume: 72, Issue:6	ent-Kaurane diterpenoids from Isodon pharicus.
AID1161837	Antiproliferative activity against human KB cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161860	Induction of apoptosis in human KB cells assessed as necrotic cells level at 10 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 3.23%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID426931	Cytotoxicity against human A549 cells after 48 hrs by SRB method	2009	Journal of natural products, Jun, Volume: 72, Issue:6	ent-Kaurane diterpenoids from Isodon pharicus.
AID1161865	Chemical stability in 10 mM pH 7.4 PBS buffer assessed as parent compound remaining at 1 uM at 37 degC after 24 hrs by HPLC method	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161864	Induction of apoptosis in human KB cells assessed as necrotic cells level at 20 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 3.23%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID426934	Cytotoxicity against human MCF7 cells after 48 hrs by SRB method	2009	Journal of natural products, Jun, Volume: 72, Issue:6	ent-Kaurane diterpenoids from Isodon pharicus.
AID1161855	Induction of apoptosis in human KB cells assessed as late apoptotic cells level at 5 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 2.26%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161861	Induction of apoptosis in human KB cells assessed as viable cells level at 20 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 87.4%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161840	Induction of apoptosis in human KB cells after 48 hrs by Annexin V and propidium iodide staining based flow cytometry	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161867	Prodrug conversion in human KB cells lysates assessed as formation of cysteine conjugates at 500 uM in presence of 10 mM cysteine by LC-HRMS method	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161854	Induction of apoptosis in human KB cells assessed as early apoptotic cells level at 5 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 7.08%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161838	Antiproliferative activity against human HL60 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161866	Stability in 80% rat plasma assessed as parent compound remaining at 1 uM at 37 degC after 24 hrs by HPLC method	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161835	Antiproliferative activity against human SGC7901 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID426930	Cytotoxicity against human NB4 cells after 48 hrs by SRB method	2009	Journal of natural products, Jun, Volume: 72, Issue:6	ent-Kaurane diterpenoids from Isodon pharicus.
AID1692271	Inhibition of ADP-induced platelet aggregation in rabbit platelet suspension preincubated for 10 mins followed by ADP stimulation by turbidimetric method	2020	Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21	Progress toward a Glycoprotein VI Modulator for the Treatment of Thrombosis.
AID1161863	Induction of apoptosis in human KB cells assessed as late apoptotic cells level at 20 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 2.26%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161859	Induction of apoptosis in human KB cells assessed as late apoptotic cells level at 10 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 2.26%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161834	Antiproliferative activity against mouse B16 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1692273	Inhibition of PAF-induced platelet aggregation in rabbit platelet suspension preincubated for 10 mins followed by PAF stimulation by turbidimetric method	2020	Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21	Progress toward a Glycoprotein VI Modulator for the Treatment of Thrombosis.
AID1161857	Induction of apoptosis in human KB cells assessed as viable cells level at 10 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 87.4%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1692274	Antagonist activity at GP6 in human platelet assessed as reduction in collagen-induced platelet-aggregation preincubated for 10 mins followed by collagen stimulation by aggregometry	2020	Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21	Progress toward a Glycoprotein VI Modulator for the Treatment of Thrombosis.
AID1692272	Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet suspension preincubated for 10 mins followed by AA stimulation by turbidimetric method	2020	Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21	Progress toward a Glycoprotein VI Modulator for the Treatment of Thrombosis.
AID1161869	Retention time of the compound in human KB cells lysates treated with 500 uM oridonin in presence of 10 mM cysteine by LC-HRMS method	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161856	Induction of apoptosis in human KB cells assessed as necrotic cells level at 5 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 3.23%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161862	Induction of apoptosis in human KB cells assessed as early apoptotic cells level at 20 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 7.08%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161836	Antiproliferative activity against human A549 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161853	Induction of apoptosis in human KB cells assessed as viable cells level at 5 uM after 48 hrs by Annexin V and propidium iodide staining based flow cytometry (Rvb = 87.4%)	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
AID1161833	Antiproliferative activity against human SMMC7721 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.04)	18.7374
1990's	3 (6.12)	18.2507
2000's	4 (8.16)	29.6817
2010's	24 (48.98)	24.3611
2020's	17 (34.69)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.35

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

Metric	This Compound (vs All)
Research Demand Index	19.35 (24.57)
Research Supply Index	3.95 (2.92)
Research Growth Index	5.66 (4.65)
Search Engine Demand Index	15.26 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (19.35)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (2.00%)	5.53%
Reviews	1 (2.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	48 (96.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.25	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2.25	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.1	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	2.25	1	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.25	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
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.	7.54	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	3.8	2	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
thiazoles [no description available]	1.98	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oleanolic acid [no description available]	2	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.08	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.08	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.05	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.05	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
imazodan imazodan: RN & structure given in first source;	1.98	1	0
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	2.25	1	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	2.25	1	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
biphenyl-2-carboxylic acid biphenyl-2-carboxylic acid: structure in first source	2.25	1	0
honokiol [no description available]	2.25	1	0	biphenyls
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.38	2	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
olmesartan olmesartan: an active metabolite of CS 866	2.25	1	0	biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent
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).	7.17	1	0	amino acid zwitterion; angiotensin II	human metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.54	2	0	cyclodextrin
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	6.98	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
lycopene [no description available]	2.25	1	0	acyclic carotene	antioxidant; plant metabolite
gw 3965 GW 3965: a liver X receptor ligand	2.25	1	0	diarylmethane
t0901317 T0901317: an LXRalpha and LXRbeta agonist	2.25	1	0
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	1.97	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.1	1	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.39	2	0
quercetin [no description available]	2.1	1	0	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
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	3.47	1	1
cinanserin Cinanserin: A serotonin antagonist with limited antihistaminic, anticholinergic, and immunosuppressive activity.. cinanserin : An aryl sulfide that is (2E)-3-phenyl-N-(2-sulfanylphenyl)prop-2-enamide in which the hydrogen of the thiol group is substituted by a 3-(dimethylamino)propyl group. It is a 5-hydroxytryptamine receptor antagonist and an inhibitor of SARS-CoV replication.	2.25	1	0	aryl sulfide; cinnamamides; secondary carboxamide; tertiary amino compound	anticoronaviral agent; antiviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
exp-3179 [no description available]	2.25	1	0
ro 19-3704 Ro 19-3704: platelet activating factor antagonist	1.98	1	0
glaucocalyxin b glaucocalyxin B: chemical constituent of Rabdhosia japonica var. glaucocalyx	2.71	3	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2	1	0
pci 32765 ibrutinib: a Btk protein inhibitor. ibrutinib : A member of the class of acrylamides that is (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies.	2.25	1	0	acrylamides; aromatic amine; aromatic ether; N-acylpiperidine; pyrazolopyrimidine; tertiary carboxamide	antineoplastic agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
lfm a13 LFM-A13 : An enamide obtained by formal condensation of the carboxy group of (2Z)-2-cyano-3-hydroxybut-2-enoic acid with the amino group of 2,5-dibromoaniline. It is a dual-function inhibitor of Bruton's tyrosine kinase (BTK) and Polo-like kinases (PLK) that exhibits anticancer properties.	2.25	1	0	aromatic amide; dibromobenzene; enamide; enol; nitrile; secondary carboxamide	antineoplastic agent; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 2.7.11.21 (polo kinase) inhibitor; geroprotector; platelet aggregation inhibitor
acp-196 acalabrutinib: inhibits Bruton’s tyrosine kinase; has antineoplastic activity. acalabrutinib : A member of the class of imidazopyrazines that is imidazo[1,5-a]pyrazine substituted by 4-(pyridin-2-ylcarbamoyl)phenyl, (2S)-1-(but-2-ynoyl)pyrrolidin-2-yl, and amino groups at positions 1, 3 and 8, respectively. It is an irreversible second-generation Bruton's tyrosine kinase (BTK) inhibitor that is approved by the FDA for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy.	2.25	1	0	aromatic amine; benzamides; imidazopyrazine; pyridines; pyrrolidinecarboxamide; secondary carboxamide; tertiary carboxamide; ynone	antineoplastic agent; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
oridonin [no description available]	2.31	1	0

Condition	Relationship Strength	Studies
Blood Clot [description not available]	2.58	2
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	7.58	2
Carcinoma, Epidermoid [description not available]	2.76	2
Cancer of Mouth [description not available]	2.41	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.76	2
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.41	1
Arthritis, Degenerative [description not available]	2.41	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.	2.41	1
Blood Poisoning [description not available]	2.41	1
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	7.41	1
Carcinoma, Non-Small Cell Lung [description not available]	2.41	1
Cancer of Lung [description not available]	2.69	2
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.41	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.69	2
Cirrhosis, Liver [description not available]	2.84	3
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.84	3
Arteriosclerosis, Coronary [description not available]	2.25	1
Innate Inflammatory Response [description not available]	2.69	2
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	2.25	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.69	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.84	3
Endotoxin Shock [description not available]	2.25	1
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	2.25	1
Anoxemia [description not available]	2.41	1
Cancer of Stomach [description not available]	2.41	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.41	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.41	1
Malignant Melanoma [description not available]	2.31	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.31	1
Adjuvant Arthritis [description not available]	2.31	1
Rheumatoid Arthritis [description not available]	7.31	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.31	1
Cancer of the Tongue [description not available]	2.31	1
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.31	1
Bone Loss, Osteoclastic [description not available]	2.31	1
Age-Related Osteoporosis [description not available]	2.31	1
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.	7.31	1
Hepatocellular Carcinoma [description not available]	2.17	1
Cancer of Liver [description not available]	2.17	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.17	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.17	1
Bladder Cancer [description not available]	7.17	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.17	1
Osteogenic Sarcoma [description not available]	2.89	3
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	2.89	3
Cirrhosis [description not available]	2.17	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.17	1
Disease Exacerbation [description not available]	2.21	1
Bone Cancer [description not available]	2.61	2
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.61	2
Benign Neoplasms [description not available]	2.57	2
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.57	2
Benign Neoplasms, Brain [description not available]	2.08	1
Astrocytoma, Grade IV [description not available]	2.08	1
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.	2.08	1
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	7.08	1
Breast Cancer [description not available]	7.08	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.08	1
Injury, Myocardial Reperfusion [description not available]	2.13	1
Heart Disease, Ischemic [description not available]	2.13	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	7.13	1
Alveolitis, Fibrosing [description not available]	2.15	1
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	7.15	1
Leucocythaemia [description not available]	2.06	1
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	7.06	1

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