ankaflavin profile

ankaflavin: from Monascus-fermented red rice; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	15294091
CHEMBL ID	1215462
MeSH ID	M0483817

Synonym
ankaflavin
CHEMBL1215462
50980-32-0
AKOS037515363
HY-N6642
(3s,3ar,9ar)-9a-methyl-3-octanoyl-6-[(e)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
(3s,3ar,9ar)-9a-methyl-3-octanoyl-6-((e)-prop-1-en-1-yl)-3a,4,8,9a-tetrahydro-2h-furo[3,2-g]isochromene-2,9(3h)-dione
CS-0062873
F82247
MS-26390
XA165909

Excerpt	Reference	Relevance
"Ankaflavin (AK) is a typical yellow pigment extracted from "	( Binding of ankaflavin with bovine serum albumin (BSA) in the presence of carrageenan and protective effects of Chen, M; Cheng, L; Deng, W; Guo, Q; Li, Z; Liu, H; Lu, J; Peng, X; Sun, Y; Wang, C; Wang, W; Wu, S; Zhao, N, 2023)	2.74
"Ankaflavin (AK) is an active compound having anti-inflammatory, anti-cancer, antiatherosclerotic, and hypolipidemic effects. "	( Ankaflavin: a natural novel PPARγ agonist upregulates Nrf2 to attenuate methylglyoxal-induced diabetes in vivo. Chang, YY; Hsu, WH; Hsu, YW; Kuo, HF; Lee, BH; Pan, TM, 2012)	3.26

Excerpt	Reference	Relevance
" Ankaflavin was found to be toxic to human cancer cell lines Hep G2 and A549 with a similar IC50 value of 15 microg/mL, while it posed no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration."	( Ankaflavin from Monascus-fermented red rice exhibits selective cytotoxic effect and induces cell death on Hep G2 cells. Ho, CY; Lee, MH; Lin, YL; Su, NW, 2005)	2.68
" Monacolin K also serves as a well-known hypolipidemic medication, but its side effect myopathy is a concern."	( Monascin and ankaflavin have more anti-atherosclerosis effect and less side effect involving increasing creatinine phosphokinase activity than monacolin K under the same dosages. Hsu, YW; Hung, YP; Lee, CL; Pan, TM, 2013)	0.76

Assay ID	Title	Year	Journal	Article
AID499311	Inhibition of yeast full-length recombinant HSP90 ATPase activity expressed in Escherichia coli strain BL21(DE3) assessed as inorganic phosphate release after 3 hrs	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499307	Antiproliferative activity against human NCI-H460 cells after 72 hrs	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499312	Binding affinity to HSP90 after 4 hrs by fluorescence polarization assay	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499309	Antiproliferative activity against human JR8 cells after 72 hrs	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499310	Antiproliferative activity against human IGROV1 cells after 72 hrs	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499308	Antiproliferative activity against human A431 cells after 72 hrs	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (2.94)	29.6817
2010's	28 (82.35)	24.3611
2020's	5 (14.71)	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	4 (11.43%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	31 (88.57%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.07	1	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.05	1	4-nitrophenols	human xenobiotic metabolite; mouse 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.	2.06	1	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
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	4.89	5	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
diosgenin [no description available]	2.06	1	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.13	1
ergosterol [no description available]	2.51	2	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.58	2	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.07	1	benzamides
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.05	1
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.05	1
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.07	1
geldanamycin [no description available]	2.05	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound	antimicrobial agent; antineoplastic agent; antiviral agent; cysteine protease inhibitor; Hsp90 inhibitor
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.05	1	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
tanespimycin CP 127374: analog of herbimycin A	2.05	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
rubropunctatin rubropunctatin: an antineoplastic pigment isolated from Monascus; structure in first source	2.13	1
monascin monascin: a pigment isolated from Monascus pilosus fermented rice; has antineoplastic activity; structure in first source. monascin : An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours.	8.61	26	alpha,beta-unsaturated ketone; gamma-lactone; organic heterotricyclic compound; polyketide	antilipemic drug; antineoplastic agent; fungal metabolite; PPARgamma agonist
monascorubrin monascorubrin: isolated from Monascus species	2.49	2	azaphilone; enone; gamma-lactone; polyketide; triketone	anti-inflammatory agent; antineoplastic agent; biological pigment; food colouring; fungal metabolite; Hsp90 inhibitor
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.07	1
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.13	1
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2.06	1
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.58	2
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.05	1
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.17	1	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	2.05	1
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.	2.05	1
Alcoholic Liver Diseases [description not available]	2.63	2
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.63	2
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	3.91	2
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	3.91	2
Breast Cancer [description not available]	2.58	2
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.17	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.58	2
Extravascular Hemolysis [description not available]	2.25	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.25	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	8.4	2
Fatty Liver, Nonalcoholic [description not available]	2.51	2
Liver Steatosis [description not available]	2.1	1
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.1	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.51	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.7	3
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.01	1
Asthma, Bronchial [description not available]	2.11	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.11	1
Injury, Ischemia-Reperfusion [description not available]	2.11	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.	7.11	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.09	1
Elevated Cholesterol [description not available]	3.09	1
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	3.09	1
Cirrhosis, Liver [description not available]	2.13	1
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.	2.13	1
Cancer of Larynx [description not available]	2.06	1
Laryngeal Neoplasms Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.	2.06	1
Age-Related Osteoporosis [description not available]	2.06	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.	2.06	1
Airway Hyper-Responsiveness [description not available]	2.07	1
Alloxan Diabetes [description not available]	2.07	1
Insulin Sensitivity [description not available]	2.07	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.07	1
Atherogenesis [description not available]	3	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	8	1
Hepatocellular Carcinoma [description not available]	2.02	1
Cancer of Liver [description not available]	2.02	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.	2.02	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.02	1

ankaflavin

Description

Cross-References

Synonyms (11)

Research Excerpts

Overview

Toxicity

Bioassays (6)

Research

Studies (34)

Market Indicators

Research Demand Index: 30.34

Study Types

ankaflavin

Description

Cross-References

Synonyms (11)

Research Excerpts

Overview

Toxicity

Bioassays (6)

Research

Studies (34)

Market Indicators

Research Demand Index: 30.34

Study Types

Related Drugs (24)

Related Conditions (41)