isohumulone profile

Isohumulone is a bitter compound found in hops, which are used in brewing beer. It is produced by the hop plant during its maturation process and is one of the primary contributors to the bitter taste of beer. Isohumulone is a prenylated chalcone derivative, synthesized via a complex series of enzymatic reactions. The biosynthesis of isohumulone involves several enzymes, including chalcone synthase, prenyltransferase, and oxidase enzymes. Isohumulone is responsible for the characteristic bitterness of beer, which is a desired attribute in many beer styles. It also contributes to the flavor and aroma of beer, although its contribution to aroma is less pronounced than that of other hop compounds. Isohumulone has been shown to possess antioxidant properties, and some research suggests that it may have health benefits. The study of isohumulone is driven by its importance in the brewing industry, its potential health benefits, and its unique chemical structure.'

isohumulone: hop-derived compound [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	93090
CHEBI ID	197058
SCHEMBL ID	316229
MeSH ID	M0216659

Synonym
isohumulone
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
CHEBI:197058
isohumulone a
3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one
25522-96-7
unii-e2s413495y
einecs 247-072-1
e2s413495y ,
SCHEMBL316229
3-penten-1-one, 1-[1,2-dihydroxy-3-isovaleryl-5-(3-methyl-2-butenyl)-4-oxo-2-cyclopenten-1-yl]-4-methyl-
QARXXMMQVDCYGZ-UHFFFAOYSA-N
2-cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-one #
3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)-1-cyclopent-2-enone
Q3155510
DTXSID90948427
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

Excerpt	Reference	Relevance
"Isohumulone treatment did not result in significant body weight gain, although pioglitazone treatment did increase body weight (10.6% increase versus control group)."	( Isohumulones, bitter acids derived from hops, activate both peroxisome proliferator-activated receptor alpha and gamma and reduce insulin resistance. Ezaki, O; Fujiwara, D; Ikeshima, E; Kanaya, T; Kondo, K; Odai, H; Oikawa, S; Shiraki, M; Tsuboyama-Kasaoka, N; Yajima, H, 2004)	2.49

Excerpt	Reference	Relevance
" The most important pharmacokinetic parameters (C(max), t(max), half life, clearance, and AUC(0-∞)) and the absolute bioavailability were determined for each class of hop acid."	( Bioavailability of hop-derived iso-α-acids and reduced derivatives. Boussery, K; Bracke, M; Cattoor, K; De Keukeleire, D; Deforce, D; Heyerick, A; Remon, JP; Van Bocxlaer, J, 2011)	0.37

Excerpt	Relevance	Reference
" dosing to New Zealand white rabbits, the absolute bioavailability for IAA was determined to be 13."	( Bioavailability of hop-derived iso-α-acids and reduced derivatives. Boussery, K; Bracke, M; Cattoor, K; De Keukeleire, D; Deforce, D; Heyerick, A; Remon, JP; Van Bocxlaer, J, 2011)	0.37
" Diet-induced obese mice (DIO) were dosed orally with KDT501 and acute effects on glucose homeostasis determined."	( Intestinal bitter taste receptor activation alters hormone secretion and imparts metabolic benefits. Albert, V; Behrens, M; Bland, JS; Fang, M; Galmozzi, A; Godio, C; Grayson, N; Kim, SM; Kim, W; Kok, BP; Littlejohn, NK; Meyerhof, W; Saez, E; Siuzdak, G; Srinivasan, S, 2018)	0.48

Class	Description
monoterpenoid	Any terpenoid derived from a monoterpene. The term includes compounds in which the C10 skeleton of the parent monoterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (10.00)	18.2507
2000's	12 (60.00)	29.6817
2010's	6 (30.00)	24.3611
2020's	0 (0.00)	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	3 (14.29%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	18 (85.71%)	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
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.03	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.03	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.02	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	3.4	1	1	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	1.98	1	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.03	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.03	1	0	catechin	antioxidant; plant metabolite
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	6.69	20	3	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	2.03	1	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
denatonium benzoate [no description available]	1.98	1	0
sucrose octaacetate sucrose octaacetate: bitter tasting cpd preferred by rats to quinine; RN given refers to ((beta-D)-fructofuranosyl)-isomer	1.98	1	0	glycoside
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.02	1	0
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.03	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.1	1	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
3-methyl-2-butene-1-thiol [no description available]	2.03	1	0	alkanethiol
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.03	1	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.03	1	0
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.98	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
brucine brucine: was heading 1991-94 (see under STRYCHNINE 1975-90); DIMETHOXYSTRYCHNINE was see BRUCINE 1975-94; use STRYCHNINE to search BRUCINE 1975-94; very toxic alkaloid from Nux vomica similar to strychnine; used as reagent in analytical chemistry; was MH 1991-94	1.98	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound
alpha bitter acid humulon: antibiotic from hops; structure	2.42	2	0	aromatic ketone; cyclic ketone; diketone; tertiary alpha-hydroxy ketone; triol	antibacterial drug; antioxidant; cyclooxygenase 2 inhibitor; metabolite
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.03	1	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	1.98	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
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.	2.02	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	2.17	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.03	1	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tenuazonic acid Tenuazonic Acid: 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.. tenuazonic acid : A member of the class of pyrrolidin-2-ones that is 5-(butan-2-yl)pyrrolidine-2,4-dione carrying an additional acetyl group at position 3. A mycotoxin produced by various plant pathogenic fungi.	2.03	1	0
reutericyclin reutericyclin: a new tetramic acid related to tenuazonic acid found in sourdough produced by Lactobacillus reuteri LTH2584 exhibits antimicrobial activity	2.03	1	0

Condition	Relationship Strength	Studies	Trials
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.85	2	1
Diabetes Mellitus, Adult-Onset [description not available]	3.85	2	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.17	1	0
Insulin Sensitivity [description not available]	4.13	3	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.85	2	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.	9.13	3	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	3.43	1	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	8.43	1	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).	8.82	2	1
Weight Gain Increase in BODY WEIGHT over existing weight.	3.4	1	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)	2.02	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.02	1	0
Cancer of Colon [description not available]	2.02	1	0
Condition, Preneoplastic [description not available]	2.02	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.02	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.02	1	0
Blood Pressure, High [description not available]	2.03	1	0
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.	2.03	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.03	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.03	1	0

isohumulone

Description

Cross-References

Synonyms (19)

Research Excerpts

Treatment

Bioavailability

Dosage Studied

Drug Classes (1)

Research

Studies (20)

Market Indicators

Research Demand Index: 34.61

Study Types