Compounds > alpha-amyrenone
Page last updated: 2024-12-07

alpha-amyrenone

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

Description

alpha-amyrenone: from Marsdenia officinalis Tsiang [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
MarsdeniagenusA plant genus of the family ASCLEPIADACEAE. Members contain pregnane glycosides (marsdekoiside & marstomentosides, maryal) and hainaneosides (SAPONINS).[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]
Marsdenia officinalisspecies[no description available]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID12306155
CHEMBL ID518475
SCHEMBL ID18821195
MeSH IDM0199751

Synonyms (11)

Synonym
alpha-amyrenone
CHEMBL518475 ,
xll7mh4ojo ,
unii-xll7mh4ojo
alfa-amyrenone
SCHEMBL18821195
Q27293894
(4ar,6ar,6bs,8ar,11r,12s,12ar,14ar,14br)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydropicen-3-one
bdbm50531261
EX-A6941
AKOS040734610

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The mixture of α,β-amyrenone, dosed orally, was able to reduce mechanical hypersensitivity and paw-oedema induced by carrageenan, interfering with neutrophil migration."( Contribution of α,β-Amyrenone to the Anti-Inflammatory and Antihypersensitivity Effects of Aleurites moluccana (L.) Willd.
Bellé Bresolin, TM; Cechinel Filho, V; Claudino, VD; da Silva Machado, M; De Souza, MM; Lucinda-Silva, RM; Malheiros, A; Meyre-Silva, C; Quintão, NL; Reichert, S; Rocha, LW; Silva, GF; Wagner, TM, 2014)		0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)40.00000.00010.995010.0000AID1617780
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (59)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1617778Inhibition of ovine recombinant COX1 assessed as decrease in formation of PGE2 using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID334272Growth inhibition of mouse B16 2F2 cells after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID1617777Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID334273Induction of melanogenesis in mouse B16 2F2 cells assessed as intracellular melanin content after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID1617779Inhibition of ovine recombinant COX1 assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617774Inhibition of human recombinant 5-LOX expressed in insect cells assessed as decrease in production of 5-HPETE and 5-HETE using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric io2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617781Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis r2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617776Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol orange as2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617775Inhibition of human recombinant 5-LOX expressed in insect cells assessed residual activity using arachidonic acid at 42 uM as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol o2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617780Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as decrease in PGE2 formation using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (28.57)18.2507
2000's1 (14.29)29.6817
2010's3 (42.86)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.3110aminonaphthalene;
naphthalenesulfonic acid		fluorescent probe
masoprocol
nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)		2.2110catechols;
lignan;
tetrol		antioxidant;
ferroptosis inhibitor;
geroprotector;
plant metabolite
glycyrrhetinic acid
[no description available]		2.2110cyclic terpene ketone;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		immunomodulator;
plant metabolite
oleanolic acid
[no description available]		3.1150hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
zileuton
[no description available]		2.21101-benzothiophenes;
ureas		anti-asthmatic drug;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
ferroptosis inhibitor;
leukotriene antagonist;
non-steroidal anti-inflammatory drug
ursolic acid
[no description available]		2.4620hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		2.0110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
medicagenic acid
medicagenic acid: aglycone constituent of lucerne saponins, upon which their fungastatic & hemolytic activity depends		2.2110triterpenoid
betulin
betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.		2.0110diol;
pentacyclic triterpenoid		analgesic;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
metabolite
beta-amyrin
beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.		3.1150pentacyclic triterpenoid;
secondary alcohol		Aspergillus metabolite;
plant metabolite
alpha-amyrin
alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.		2.4620pentacyclic triterpenoid;
secondary alcohol
hederagenin
[no description available]		2.2110dihydroxy monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin		plant metabolite
betulinic acid methyl ester
betulinic acid methyl ester: from the roots of Saussurea lappa; structure in first source		2.0110triterpenoid
arjunolic acid
arjunolic acid: oleanane type; isol from Cochlospermum tinctorium (Bixaceae); structure given in first source; RN given refers to (2alpha,3beta,4alpha)-isomer; RN for cpd without isomeric designation not avail 12/89. arjunolic acid : A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.		2.2110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite
maslinic acid
(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria		2.2110dihydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
plant metabolite
3-acetyllupeol
3-acetyllupeol: from root of Euphorbia fischeriana Steud; RN refers to (3beta)-isomer		2.0110organic molecular entitymetabolite
lupenone
lupenone: structure in first source		2.4420triterpenoidmetabolite
uvaol
uvaol: from Vauquelinia corymbosa (Rosaceae)		2.4620triterpenoidmetabolite
gypsogenin
gypsogenin: originally from Gypsophila species; structure in first source. gypsogenin : A sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23.		2.2110aldehyde;
monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin
Lup-20(29)-en-28-al, 3beta-hydroxy-
[no description available]		2.0110triterpenoid
erythrodiol
[no description available]		2.4620diol;
pentacyclic triterpenoid;
primary alcohol;
secondary alcohol		plant metabolite
taraxasterol
taraxasterol: from Cirsium segetum. taraxasterol : A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3.		2.0710pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory agent;
metabolite
asiatic acid
[no description available]		2.2110monocarboxylic acid;
pentacyclic triterpenoid;
triol		angiogenesis modulating agent;
metabolite
boswellic acid
boswellic acid: ursane type; RN given refers to (3alpha,4beta)-isomer; active principle of salai guggal; see also record for salai guggal		2.2110triterpenoid
lupeol
[no description available]		2.4420pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
amyrin acetate
[no description available]		1.9710
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.3110cyclodextrin
betulonal
betulonal: originally isolated from white birch bark (Betula pendula); structure in first source		2.0110
boswellic acid
[no description available]		2.2110
orlistat
Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.		2.3110beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative		anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
sc 560
SC560 : A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors, SC-560 is selective for COX-1.		2.2110aromatic ether;
monochlorobenzenes;
organofluorine compound;
pyrazoles		angiogenesis modulating agent;
antineoplastic agent;
apoptosis inducer;
cyclooxygenase 1 inhibitor;
non-steroidal anti-inflammatory drug
corosolic acid
[no description available]		2.2110triterpenoidmetabolite
11-keto-boswellic acid
[no description available]		2.2110
betulone
[no description available]		2.0110triterpenoidmetabolite
acetyl-11-ketoboswellic acid
acetyl-11-ketoboswellic acid: a 5-lipoxygenase inhibitor; structure given in first source		2.2110triterpenoid
3-o-acetyl-beta-boswellic acid
3-O-acetyl-beta-boswellic acid: isolated from Boswellia serrata; structure in first source		2.2110
11-deoxy glycyrrhetinic acid
[no description available]		2.2110triterpenoid
ConditionIndicatedRelationship StrengthStudiesTrials
B16 Melanoma
[description not available]		02.0110
Anasarca
[description not available]		02.110
Allergic Reaction
[description not available]		02.110
Innate Inflammatory Response
[description not available]		02.110
Ache
[description not available]		02.110
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.110
Hypersensitivity
Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.		02.110
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.		02.110
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.110