Page last updated: 2024-12-06

Tormentic acid

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

Description

Tormentic acid is a triterpenoid compound found in various plants, including the European mountain ash (Sorbus aucuparia) and the Japanese rowan (Sorbus commixta). It has been shown to possess anti-inflammatory, antioxidant, and anti-cancer properties. Research on tormentic acid focuses on understanding its biological mechanisms and exploring its potential therapeutic applications. The compound is synthesized via a complex biosynthetic pathway involving multiple enzymatic steps. It is often studied for its potential use in treating inflammatory conditions, such as rheumatoid arthritis, as well as for its ability to protect cells from oxidative stress. Tormentic acid's anti-cancer properties have also garnered interest, with studies investigating its effects on different cancer cell lines.'

tormentic acid: aglycone of Rosamultin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73193
CHEMBL ID239077
CHEBI ID70682
SCHEMBL ID94231

Synonyms (31)

Synonym
2.alpha.,19.alpha.-trihydroxy-urs-12-en-28-oic acid
nsc720893
nsc-720893
(1r,2r,4as,6ar,6as,6br,8ar,10r,11r,12ar,14bs)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
2.alpha.,3.alpha.,19.alpha.-trihydroxyurs-12-en-28-oic acid
13850-16-3
tormentic acid
chebi:70682 ,
tomentic acid
CHEMBL239077
2,3,19-trihydroxyurs-12-en-28-oic acid (2alpha,3beta)-
9wl8lh7u78 ,
urs-12-en-28-oic acid, 2,3,19-trihydroxy-, (2alpha,3beta)-
unii-9wl8lh7u78
SCHEMBL94231
AKOS032962136
HY-N4137
(1r,2r,4as,6as,6br,8ar,10r,11r,12ar,12br,14bs)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
DTXSID40930135
2,3,19-trihydroxyurs-12-en-28-oic acid
Q15634134
CS-0032207
bdbm50593989
tormenticacid
urs-12-en-28-oic acid, 2,3,19-trihydroxy-, (2.alpha.,3.beta.)-
2.alpha.,3.beta.,19-trihydroxyurs-12-en-28-oic acid
tormentolic acid
urs-12-en-28-oic acid, 2.alpha.,3.beta.,19-trihydroxy-
2.alpha.,19.alpha.-dihydroxyursolic acid
2.alpha.,3.beta.,19.alpha.-trihydroxyurs-12-en-28-oic acid
(2.alpha.,3.beta.)-2,3,19-trihydroxyurs-12-en-28-oic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
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 (1)

ClassDescription
triterpenoidAny terpenoid derived from a triterpene. The term includes compounds in which the C30 skeleton of the parent triterpene 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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sentrin-specific protease 1Homo sapiens (human)IC50 (µMol)4.30000.00642.64466.1000AID1868240
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IISentrin-specific protease 1Homo sapiens (human)
proteolysisSentrin-specific protease 1Homo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processSentrin-specific protease 1Homo sapiens (human)
protein sumoylationSentrin-specific protease 1Homo sapiens (human)
protein desumoylationSentrin-specific protease 1Homo sapiens (human)
regulation of mRNA stabilitySentrin-specific protease 1Homo sapiens (human)
apoptotic signaling pathwaySentrin-specific protease 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
endopeptidase activitySentrin-specific protease 1Homo sapiens (human)
protein bindingSentrin-specific protease 1Homo sapiens (human)
deSUMOylase activitySentrin-specific protease 1Homo sapiens (human)
SUMO-specific endopeptidase activitySentrin-specific protease 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleoplasmSentrin-specific protease 1Homo sapiens (human)
cytoplasmSentrin-specific protease 1Homo sapiens (human)
focal adhesionSentrin-specific protease 1Homo sapiens (human)
nuclear membraneSentrin-specific protease 1Homo sapiens (human)
nucleusSentrin-specific protease 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID682480Induction of apoptosis in human 518A2 cells after 24 to 48 hrs by DNA laddering assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID402091Antiviral activity against HIV1 3B in human H9 cells after 4 days by p24 antigen ELISA1998Journal of natural products, Sep, Volume: 61, Issue:9
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
AID682478Induction of apoptosis in human 8505C cells assessed as migration of phosphatidylserine from inner to outer cell membrane at 30 uM after 6 hrs by Annexin V-FITC/PI based FACS analysis2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1868244Cytotoxicity against human SK-OV-3 cells assessed as cell viability at 500 uM incubated for 48 hrs by SRB assay2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID1165539Anti-inflammatory activity in mouse RAW264.7 cells assessed as inhibition of lipopolysaccharide-induced nitric oxide production incubated for 24 hrs by Griess reagent based assay2014Journal of natural products, Oct-24, Volume: 77, Issue:10
Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia.
AID1416504Cytotoxicity against human Bel7402 cells after 24 hrs by MTT assay2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID1416511Induction of morphological changes in human MCF7 cells after 24 hrs by phase contrast microscopic method2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID682467Cytotoxicity against human A2780 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID682464Cytotoxicity against human 518A2 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1868242Cytotoxicity against human SK-OV-3 cells assessed as reduction in cell viability at 25 uM incubated for 48 hrs by SRB assay2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID1416503Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID302037Cytotoxicity against human multidrug resistant Lucena1 cells assessed as cell viability after 48 hrs by MTT assay2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Natural triterpenoids from Cecropia lyratiloba are cytotoxic to both sensitive and multidrug resistant leukemia cell lines.
AID1868239Inhibition of recombinant human SENP1 assessed as reduction in deSUMOylation of RanGAP1-SUMO1 at 5 uM using RanGAP1-SUMO1 as substrate preincubated for 10 mins followed by substrate addition and measured after 30 mins relative to control2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID527183Cytotoxicity against human HT-29 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID682470Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1416507Cytotoxicity against human HepG2 cells assessed as inhibition of cell proliferation at 100 ug/ml after 24 hrs by MTT assay relative to control2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID682468Cytotoxicity against human A549 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID354613Inhibition of HIV1 recombinant protease expressed in Escherichia coli DH5alpha at 17.9 ug/mL after 2 hrs by HPLC assay1996Journal of natural products, Jul, Volume: 59, Issue:7
Anti-HIV triterpene acids from Geum japonicum.
AID1416509Cytotoxicity against human A549 cells assessed as inhibition of cell proliferation at 100 ug/ml after 24 hrs by MTT assay relative to control2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID682477Induction of apoptosis in human 8505C cells assessed as induction of cell death after 24 to 48 hrs by AO/PI exclusion dye assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID527182Cytotoxicity against human NCI-H460 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID1416510Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferation at 100 ug/ml after 24 hrs by MTT assay relative to control2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID1416508Cytotoxicity against human Bel7402 cells assessed as inhibition of cell proliferation at 100 ug/ml after 24 hrs by MTT assay relative to control2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID1416505Cytotoxicity against human A549 cells after 24 hrs by MTT assay2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID527184Cytotoxicity against human CEM cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID1416506Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay2017MedChemComm, Aug-01, Volume: 8, Issue:8
Extraction of antioxidant and antiproliferative ingredients from fruits of
AID682472Cytotoxicity against human WW030272 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1868243Cytotoxicity against human SK-OV-3 cells assessed as reduction in cell viability incubated for 48 hrs by SRB assay2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID1165541Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 40 uM by MTT assay2014Journal of natural products, Oct-24, Volume: 77, Issue:10
Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia.
AID1868240Inhibition of recombinant human SENP1 assessed as reduction in deSUMOylation using RanGAP1-SUMO1 as substrate preincubated for 10 mins followed by substrate addition and measured after 30 mins2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID402092Cytotoxicity against mock-infected human H9 cells after 4 days1998Journal of natural products, Sep, Volume: 61, Issue:9
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
AID682469Cytotoxicity against human DLD1 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1364711Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM incubated for 24 hrs by MTT assay relative to untreated control2017Journal of natural products, 04-28, Volume: 80, Issue:4
Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID458321Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as reduction of cortisone to cortisol conversion at 20 uM by scintillation counting2010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches.
AID682471Cytotoxicity against mouse NIH/3T3 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID682466Cytotoxicity against human A253 cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID527185Cytotoxicity against human fibroblast cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID1868246Synergistic reversal of platinum resistance in cisplatin-resistant human SK-OV-3 cells assessed as combination index after 48 hrs in presence of cisplatin by SRB assay2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID1868241Inhibition of SENP1 in human SK-OV-3 cells assessed as increase in SUMOlytated JAK2 level at 5 uM after 48 hrs by immunoprecipitation method2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
AID527181Cytotoxicity against human MCF7 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID302036Cytotoxicity against human K562 cells assessed as cell viability after 48 hrs by MTT assay2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Natural triterpenoids from Cecropia lyratiloba are cytotoxic to both sensitive and multidrug resistant leukemia cell lines.
AID458318Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as reduction of cortisone to cortisol conversion by scintillation counting2010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches.
AID1364710Neuroprotective activity in rat C6 cells assessed as induction of nerve growth factor secretion at 20 uM incubated for 24 hrs by ELISA method relative to untreated control2017Journal of natural products, 04-28, Volume: 80, Issue:4
Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID682481Induction of apoptosis in human 8505C cells after 24 to 48 hrs by DNA laddering assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID682465Cytotoxicity against human 8505C cells after 96 hrs by SRB assay2012European journal of medicinal chemistry, Oct, Volume: 56Tormentic acid derivatives: synthesis and apoptotic activity.
AID1868245Reversal of platinum resistance in cisplatin-resistant human SK-OV-3 cells assessed as reduction in cisplatin IC50 after 48 hrs in presence of cisplatin by SRB assay (Rvb = 28.23 microM)2022Journal of natural products, 05-27, Volume: 85, Issue:5
Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (9.52)18.2507
2000's1 (4.76)29.6817
2010's6 (28.57)24.3611
2020's12 (57.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.78

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 Index27.78 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.76%)5.53%
Reviews2 (9.52%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]