Compounds > auriculasin
Page last updated: 2024-12-11

auriculasin

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

Description

auriculasin: isolated from the fruits of Maclura pomifera; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
MacluragenusA plant genus of the family MORACEAE. Members contain maclurin, antifungal chalcones, and other compounds.[MeSH]MoraceaeThe mulberry plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. They have milky latex and small, petalless male or female flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID5358846
CHEMBL ID459129
CHEBI ID178564
MeSH IDM0506215

Synonyms (18)

Synonym
CHEBI:178564
7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
cudraisoflavone a
NSC285656 ,
auriculasin
60297-37-2
nsc-285656
CHEMBL459129
LMPK12050247
bdbm50442400
DTXSID50418510
ncgc00384963-01!7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
FS-8648
7-(3,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)-2h,6h-pyrano[3,2-g]chromen-6-one
nsc 285656
HY-N2911
CS-0023510
AKOS040761390

Research Excerpts

Effects

ExcerptReferenceRelevance
"Auriculasin has a wide range of pharmacological effects, including anticancer and anti-inflammatory effects. "( In Vitro Metabolism of Auriculasin and Its Inhibitory Effects on Human Cytochrome P450 and UDP-Glucuronosyltransferase Enzymes.
Ge, G; Guo, Z; Shan, L; Shi, X; Song, Y; Su, D; Zhang, G, 2019)		2.27
"Auriculasin has a wide range of pharmacological effects, including anticancer and anti-inflammatory effects. "( In Vitro Metabolism of Auriculasin and Its Inhibitory Effects on Human Cytochrome P450 and UDP-Glucuronosyltransferase Enzymes.
Ge, G; Guo, Z; Shan, L; Shi, X; Song, Y; Su, D; Zhang, G, 2019)		2.27

Treatment

ExcerptReferenceRelevance
"Auriculasin treatment resulted in selective apoptotic cell death in LNCaP prostate cancer cells, characterized by DNA fragmentation, accumulation of sub-G1 cell population, cleavage of poly (ADP-ribose) polymerase (PARP), regulation of Bax/Bcl-2 ratio, increase of cytosolic apoptosis-inducing factor (AIF) and endonuclease G (EndoG), in addition to inhibiting tumor growth in a xenograft mouse model."( Auriculasin-induced ROS causes prostate cancer cell death via induction of apoptosis.
Cho, HD; Lee, JH; Lee, MK; Moon, KD; Park, KH; Seo, KI, 2018)		2.64
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoflavanonesMembers of the class of isoflavans that have a 3,4-dihydro-3-aryl-2H-1-benzopyran-4-one skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Plasma kallikreinHomo sapiens (human)Ki4.40000.00023.34749.6000AID1271911
SialidaseClostridium perfringensIC50 (µMol)0.30000.00102.45729.8000AID779446
SialidaseClostridium perfringensKi0.13000.10301.97847.4100AID779447
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)3.60000.00053.49849.7600AID1271910
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)Ki4.40000.19004.83279.6000AID1271911
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

Processvia Protein(s)Taxonomy
Factor XII activationPlasma kallikreinHomo sapiens (human)
proteolysisPlasma kallikreinHomo sapiens (human)
blood coagulationPlasma kallikreinHomo sapiens (human)
zymogen activationPlasma kallikreinHomo sapiens (human)
plasminogen activationPlasma kallikreinHomo sapiens (human)
fibrinolysisPlasma kallikreinHomo sapiens (human)
positive regulation of fibrinolysisPlasma kallikreinHomo sapiens (human)
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityPlasma kallikreinHomo sapiens (human)
protein bindingPlasma kallikreinHomo sapiens (human)
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
extracellular regionPlasma kallikreinHomo sapiens (human)
extracellular spacePlasma kallikreinHomo sapiens (human)
plasma membranePlasma kallikreinHomo sapiens (human)
extracellular exosomePlasma kallikreinHomo sapiens (human)
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID354483Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as mouse bearing papillomas at 85 nmol administered 1 hr before TPA treatment measured after 8 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID1271910Inhibition of human recombinant PTP1B using p-nitrophenyl phosphate as substrate by spectrophotometric analysis2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Novel chromenedione derivatives displaying inhibition of protein tyrosine phosphatase 1B (PTP1B) from Flemingia philippinensis.
AID1385658Antibacterial activity against Staphylococcus aureus TISTR 1466 by 2-fold serial dilution method2018Journal of natural products, 08-24, Volume: 81, Issue:8
Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa.
AID354482Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as number of skin papillomas per mouse at 85 nmol administered 1 hr before TPA treatment measured after 20 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID779447Non-competitive inhibition of Clostridium perfringens neuraminidase using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by Dixon plot method2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Bacterial neuraminidase inhibitory effects of prenylated isoflavones from roots of Flemingia philippinensis.
AID1385661Antibacterial activity against Pseudomonas aeruginosa TISTR 292 by 2-fold serial dilution method2018Journal of natural products, 08-24, Volume: 81, Issue:8
Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa.
AID779446Inhibition of Clostridium perfringens neuraminidase using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by fluorimetry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Bacterial neuraminidase inhibitory effects of prenylated isoflavones from roots of Flemingia philippinensis.
AID354487Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as number of skin papillomas per mouse at 85 nmol administered 1 hr before TPA treatment measured after 17 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID1271911Non-competitive inhibition of human recombinant PTP1B using p-nitrophenyl phosphate as substrate by spectrophotometry based Lineweaver-Burk plot2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Novel chromenedione derivatives displaying inhibition of protein tyrosine phosphatase 1B (PTP1B) from Flemingia philippinensis.
AID1385659Antibacterial activity against Staphylococcus epidermidis ATCC 12228 by 2-fold serial dilution method2018Journal of natural products, 08-24, Volume: 81, Issue:8
Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa.
AID1385657Antibacterial activity against Bacillus subtilis TISTR 008 by 2-fold serial dilution method2018Journal of natural products, 08-24, Volume: 81, Issue:8
Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa.
AID354486Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as number of skin papillomas per mouse at 85 nmol administered 1 hr before TPA treatment measured after 14 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID354485Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as mouse bearing papillomas at 85 nmol administered 1 hr before TPA treatment measured after 20 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID354484Inhibition of DMBA-induced/TPA-promoted carcinogenesis in ICR mouse assessed as mouse bearing papillomas at 85 nmol administered 1 hr before TPA treatment measured after 10 weeks2004Journal of natural products, Jul, Volume: 67, Issue:7
Chemical constituents of Millettia taiwaniana: structure elucidation of five new isoflavonoids and their cancer chemopreventive activity.
AID1385660Antibacterial activity against Salmonella typhimurium TISTR 781 by 2-fold serial dilution method2018Journal of natural products, 08-24, Volume: 81, Issue:8
Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (14.29)29.6817
2010's9 (64.29)24.3611
2020's3 (21.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.13

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

MetricThis Compound (vs All)
Research Demand Index20.13 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.20 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pomiferin
pomiferin: structure in first source		2.1510isoflavanones
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.		2.4110dialdehydebiomarker
vancomycin
Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.		2.1710glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite
ursolic acid
[no description available]		2.1310hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
gentamicin c1
[no description available]		2.1710
tetrandrine
tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity		3.4110bisbenzylisoquinoline alkaloid;
isoquinolines
inermin
inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.		2.1710maackiain
osajin
osajin: from Maclura pomifera		2.8130isoflavanones
6,8-diprenylgenistein
6,8-diprenylgenistein: a lysoPAF acetyltransferase inhibitor isolated from licorice root; structure in first source. 5,7,4'-trihydroxy-6,8-diprenylisoflavone : A member of the class of 7-hydroxyisoflavones that is genistein substituted by prenyl groups at positions 6 and 8. It has been isolated from Derris scandens and Glycyrrhiza uralensis.		2.51207-hydroxyisoflavonesantibacterial agent;
plant metabolite
genistein
[no description available]		2.08107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
andrographolide
[no description available]		3.4110carbobicyclic compound;
gamma-lactone;
labdane diterpenoid;
primary alcohol;
secondary alcohol		anti-HIV agent;
anti-inflammatory drug;
antineoplastic agent;
metabolite
warangalone
warangalone: structure in first source		2.7830
ConditionIndicatedRelationship StrengthStudiesTrials
Colorectal Cancer
[description not available]		07.4110
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.4110
Benign Neoplasms
[description not available]		03.2310
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.		03.2310
Cancer of Prostate
[description not available]		02.5920
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.5920
ADDH
[description not available]		02.1710
Attention Deficit Disorder with Hyperactivity
A behavior disorder originating in childhood in which the essential features are signs of developmentally inappropriate inattention, impulsivity, and hyperactivity. Although most individuals have symptoms of both inattention and hyperactivity-impulsivity, one or the other pattern may be predominant. The disorder is more frequent in males than females. Onset is in childhood. Symptoms often attenuate during late adolescence although a minority experience the full complement of symptoms into mid-adulthood. (From DSM-V)		02.1710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0310
Anasarca
[description not available]		02.0310
Ache
[description not available]		02.0310
Gastric Ulcer
[description not available]		02.0310
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.0310
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.0310
Stomach Ulcer
Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).		02.0310