Page last updated: 2024-11-08

alpha bitter acid

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

Description

humulon: antibiotic from hops; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID442911
CHEMBL ID1592914
CHEMBL ID3814665
CHEBI ID5769
SCHEMBL ID144835
SCHEMBL ID13629033
SCHEMBL ID17584889
MeSH IDM0051460

Synonyms (31)

Synonym
26472-41-3
NCGC00160174-01
(6r)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
CHEBI:5769
humulon
(6r)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
(6r)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone
alpha-humulon
SCHEMBL144835
SCHEMBL13629033
2,4-cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-, (r)-
2,4-cyclohexadien-1-one, 3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methyl-2-butenyl)-, (r)-(-)-
VMSLCPKYRPDHLN-OAQYLSRUSA-N
3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one #
CHEMBL1592914
CHEMBL3814665 ,
SCHEMBL17584889
alpha-lupulic acid
alpha-bitter acid
((r)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1oxobutyl)-2,4-cyclohexadien-1-one)
ncgc00160174-01!humulone
bdbm50177000
humulone (r-humulone)
Q419456
(+)-humulone
DTXSID501019081
(-)-(r)-humulone
2,4-cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-, (6r)-
MS-25761
CS-0032512
HY-N6084

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Preliminary pharmacokinetics of these compounds in humans shows relatively small interindividual differences and an estimated short half-life of ∼30 min."( Pharmacokinetics of iso-α-acids in volunteers following the consumption of beer.
Drummer, OH; Gerostamoulos, D; Rodda, LN,
)
0.13
" Preliminary pharmacokinetics of these compounds in humans shows relatively small inter-individual differences and an estimated short half-life varying between ∼38 and 46min for the three groups."( Pharmacokinetics of reduced iso-α-acids in volunteers following clear bottled beer consumption.
Drummer, OH; Gerostamoulos, D; Rodda, LN, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" 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
" Further studies are needed to determine the bioavailability of these compounds and their possible beneficial health effects when taken by moderate beer consumption."( Beer and beer compounds: physiological effects on skin health.
Becker, T; Chen, W; Qian, F; Ring, J, 2014
)
0.4

Dosage Studied

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

Roles (4)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (5)

ClassDescription
diketoneA compound that contains two ketone functionalities.
triolA chemical compound containing three hydroxy groups.
cyclic ketone
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl 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]

Pathways (2)

PathwayProteinsCompounds
lupulone and humulone biosynthesis416
superpathway of bitter acids biosynthesis525

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency89.12510.354828.065989.1251AID504847
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency17.90080.00798.23321,122.0200AID2546; AID2551
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)IC50 (µMol)9.65000.00011.68479.3200AID1304625; AID1304628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
negative regulation of endothelial cell proliferationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte chemotaxis involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte migration involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
humoral immune responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of bone mineralizationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dendritic cell migrationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
glucose homeostasisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of fat cell differentiationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of insulin secretionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of vascular wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory response to woundingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cytokine production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cellular response to oxidative stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene A4 biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of sprouting angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cellPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxin biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
arachidonate 5-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
iron ion bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
protein bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
hydrolase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
extracellular spacePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelope lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nucleoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear matrixPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear membranePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
secretory granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
perinuclear region of cytoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
ficolin-1-rich granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1304629Inhibition of 5-LO in human polymorphonuclear leukocytes assessed as residual activity at 10 uM preincubated for 10 mins followed by addition of arachidonic acid as substrate measured after 10 mins by HPLC method relative to control2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
AID1304631Inhibition of mPGES-1 in microsomes of IL1-beta induced human A549 cells assessed as PGE2 formation by measuring enzyme residual activity at 10 uM preincubated for 15 mins followed by addition of PGH2 as substrate measured after 1 min by RP-HPLC method re2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
AID1304625Inhibition of recombinant human 5-LO expressed in Escherichia coli MV1190 cells preincubated for 10 mins followed by addition of arachidonic acid as substrate measured after 10 mins by RP-HPLC method2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
AID1304628Inhibition of 5-LO in human polymorphonuclear leukocytes preincubated for 10 mins followed by addition of arachidonic acid as substrate measured after 10 mins by HPLC method2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (9.38)18.7374
1990's8 (12.50)18.2507
2000's19 (29.69)29.6817
2010's21 (32.81)24.3611
2020's10 (15.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.89

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.89 (24.57)
Research Supply Index4.23 (2.92)
Research Growth Index4.87 (4.65)
Search Engine Demand Index50.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.49%)5.53%
Reviews3 (4.48%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other63 (94.03%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]