Compounds > betulinic acid methyl ester
Page last updated: 2024-11-06

betulinic acid methyl ester

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Description

Betulinic acid methyl ester is a derivative of betulinic acid, a naturally occurring pentacyclic triterpenoid found in various plants. It has gained considerable attention in the field of medicinal chemistry due to its promising anti-cancer activity. It exhibits anti-proliferative effects against several cancer cell lines, including melanoma, leukemia, and prostate cancer. The compound's mechanism of action involves inhibiting cell growth and inducing apoptosis in cancer cells. It is currently under investigation as a potential therapeutic agent for cancer treatment. Betulinic acid methyl ester is typically synthesized via esterification of betulinic acid with methanol in the presence of an acid catalyst.'

betulinic acid methyl ester: from the roots of Saussurea lappa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
SaussureagenusA plant genus of the family ASTERACEAE, order Asterales, subclass Asteridae. It is a source of costus root oil and should not be confused with the genus COSTUS.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID73493
CHEMBL ID295602
CHEBI ID184030
SCHEMBL ID2421615
MeSH IDM0529025

Synonyms (25)

Synonym
lup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3.beta.)-
NSC152532 ,
28-o-methylbetulinic acid
2259-06-5
methyl (1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
methyl betulinate
betulinic acid methyl ester
(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1h-cyclopenta[a]chrysene-3a-carboxylate
(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid methyl ester
bdbm50240501
(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1h-cyclopenta[a]chrysene-3a-carboxylate
methyl 3-hydroxylup-20(29)-en-28-oate
methyl 3beta-hydroxylup-20(29)-en-28-oate
betulinic acid methylester
CHEMBL295602 ,
CHEBI:184030
methyl (1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
nsc 152532
einecs 218-857-6
SCHEMBL2421615
mfcd00017379
AKOS027381477
betulinate, methyl
CS-0034288
HY-N6587
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 2Bos taurus (cattle)Ki50.00000.00251.13257.5858AID1188769
Botulinum neurotoxin type A Clostridium botulinumIC50 (µMol)100.00000.50003.16927.2000AID590854
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled bile acid receptor 1Homo sapiens (human)EC50 (µMol)10.00000.02372.52598.9000AID444761
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
angiotensin-activated signaling pathwayCarbonic anhydrase 2Bos taurus (cattle)
regulation of monoatomic anion transportCarbonic anhydrase 2Bos taurus (cattle)
regulation of intracellular pHCarbonic anhydrase 2Bos taurus (cattle)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Bos taurus (cattle)
cell surface bile acid receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeG-protein coupled bile acid receptor 1Homo sapiens (human)
cellular response to bile acidG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of cholangiocyte proliferationG-protein coupled bile acid receptor 1Homo sapiens (human)
regulation of bicellular tight junction assemblyG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 2Bos taurus (cattle)
cyanamide hydratase activityCarbonic anhydrase 2Bos taurus (cattle)
protein transmembrane transporter activityBotulinum neurotoxin type A Clostridium botulinum
protein bindingG-protein coupled bile acid receptor 1Homo sapiens (human)
bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
cytoplasmCarbonic anhydrase 2Bos taurus (cattle)
plasma membraneCarbonic anhydrase 2Bos taurus (cattle)
cytoplasmG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
receptor complexG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (45)

Assay IDTitleYearJournalArticle
AID484833Cytotoxicity against human A431 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID484832Cytotoxicity against human A253 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID770953Cytotoxicity against human A549 cells assessed as cell viability after 96 hrs by SRB assay2013European journal of medicinal chemistry, Oct, Volume: 68Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
AID402978Cytotoxicity against human CEM cells after 72 hrs by MTT assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
AID770955Cytotoxicity against human MCF7 cells assessed as cell viability after 96 hrs by SRB assay2013European journal of medicinal chemistry, Oct, Volume: 68Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
AID444763Agonist activity at human FXR expressed in COS1 cells by luciferase reporter gene assay2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.
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.
AID444761Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporter gene assay2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.
AID402981Cytotoxicity against paclitaxel-resistant human K562 cells after 72 hrs by MTT assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
AID770958Cytotoxicity against human A2780 cells assessed as cell viability after 96 hrs by SRB assay2013European journal of medicinal chemistry, Oct, Volume: 68Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
AID338358Cytotoxicity against human Raji cells assessed as cell viability at 10 mol ratio after 48 hrs relative to TPA
AID482909Cytotoxicity against human SW1736 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID484834Cytotoxicity against human A549 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID590854Inhibition of Clostridium BoNT/A protease light chain2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease.
AID338352Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 100 mol ratio after 48 hrs relative to TPA
AID95520Cytotoxicity against human epidermoid carcinoma of the mouth (KB) cell line.1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis of betulinic acid derivatives with activity against human melanoma.
AID338357Cytotoxicity against human Raji cells assessed as cell viability at 100 mol ratio after 48 hrs relative to TPA
AID1188769Inhibition of bovine erythrocyte carbonic anhydrase 2 using 4-nitrophenyl acetate substrate by photometric assay2014European journal of medicinal chemistry, Oct-30, Volume: 86Sulfamates of methyl triterpenoates are effective and competitive inhibitors of carbonic anhydrase II.
AID468092Antiviral activity against SFV infected in BHK cells assessed as surviving virus fraction at 50 uM after 14 hrs by luciferase reporter gene assay2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID106299Cytotoxicity against cultured human melanoma (MEL-2) cell line.1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis of betulinic acid derivatives with activity against human melanoma.
AID482907Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID402980Cytotoxicity against human K562 cells after 72 hrs by MTT assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
AID482902Cytotoxicity against human DLD1 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID402979Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
AID482908Cytotoxicity against human SW480 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID402982Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
AID468095Cytotoxicity against human HuH7 cells assessed as cell viability at 50 uM after 24 hrs2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID484829Cytotoxicity against human 518A2 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID338355Cytotoxicity against human Raji cells assessed as cell viability at 5000 mol ratio after 48 hrs relative to TPA
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.
AID482906Cytotoxicity against human Liposarcoma cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID482905Cytotoxicity against human HT-29 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID482903Cytotoxicity against human HCT8 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID482901Cytotoxicity against human A2780 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID484831Cytotoxicity against human 8505C cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID338350Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 5000 mol ratio after 48 hrs relative to TPA
AID338353Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 10 mol ratio after 48 hrs relative to TPA
AID770957Cytotoxicity against human 8505C cells assessed as cell viability after 96 hrs by SRB assay2013European journal of medicinal chemistry, Oct, Volume: 68Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
AID338354Inhibition of EBV-early antigen activation in human Raji cells assessed as early antigen activation at 1 uM ratio after 48 hrs
AID482904Cytotoxicity against human HCT116 cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID444762Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporter gene assay relative to litocholic acid2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.
AID338356Cytotoxicity against human Raji cells assessed as cell viability at 1000 mol ratio after 48 hrs relative to TPA
AID484830Cytotoxicity against human FADU cells after 96 hrs by SRB assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity.
AID338351Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 1000 mol ratio after 48 hrs relative to TPA
AID770956Cytotoxicity against human 518A2 cells assessed as cell viability after 96 hrs by SRB assay2013European journal of medicinal chemistry, Oct, Volume: 68Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (8.33)18.2507
2000's4 (33.33)29.6817
2010's6 (50.00)24.3611
2020's1 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.46

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

MetricThis Compound (vs All)
Research Demand Index12.46 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.46)

All Compounds (24.57)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetazolamide
Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)		2.110monocarboxylic acid amide;
sulfonamide;
thiadiazoles		anticonvulsant;
diuretic;
EC 4.2.1.1 (carbonic anhydrase) inhibitor
flumazenil
Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.		3.0110ethyl ester;
imidazobenzodiazepine;
organofluorine compound		antidote to benzodiazepine poisoning;
GABA antagonist
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		2.0510butan-4-olidemetabolite;
neurotoxin
lithocholic acid
Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.		2.0510bile acid;
C24-steroid;
monohydroxy-5beta-cholanic acid		geroprotector;
human metabolite;
mouse metabolite
oleanolic acid
[no description available]		2.4320hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
ribavirin
Rebetron: Rebetron is tradename		2.05101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
ursolic acid
[no description available]		2.4320hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		3.6490hydroxy 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
platanic acid
platanic acid: inhibits HIV replication; isolated from Syzigium claviflorum; structure in first source. platanic acid : A pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3beta-hydroxy and an oxo group at position 20. It is isolated from the leaves of Syzygium claviflorum and exhibits anti-HIV activity.		2.4720hydroxy monocarboxylic acid;
methyl ketone;
pentacyclic triterpenoid		anti-HIV agent;
metabolite
3'-amino-3'-deoxyadenosine
[no description available]		2.0510
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.		2.9440diol;
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.		2.0110pentacyclic 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.		2.4320pentacyclic triterpenoid;
secondary alcohol
dehydrocostus lactone
dehydrocostus lactone : An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.		2.0510gamma-lactone;
guaiane sesquiterpenoid;
organic heterotricyclic compound;
sesquiterpene lactone		antimycobacterial drug;
antineoplastic agent;
apoptosis inducer;
cyclooxygenase 2 inhibitor;
metabolite;
trypanocidal drug
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.		2.0510hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite
friedelin
3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.		2.0510cyclic terpene ketone;
pentacyclic triterpenoid		anti-inflammatory drug;
antipyretic;
non-narcotic analgesic;
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		2.4320triterpenoidmetabolite
uvaol
uvaol: from Vauquelinia corymbosa (Rosaceae)		2.4320triterpenoidmetabolite
Lup-20(29)-en-28-al, 3beta-hydroxy-
[no description available]		2.4320triterpenoid
erythrodiol
[no description available]		2.0110diol;
pentacyclic triterpenoid;
primary alcohol;
secondary alcohol		plant metabolite
asiatic acid
[no description available]		2.0510monocarboxylic acid;
pentacyclic triterpenoid;
triol		angiogenesis modulating agent;
metabolite
betulonic acid
betulonic acid: isolated from Rush javanica; strucure in first source		3.2960triterpenoidanticoronaviral agent
mokko lactone
mokko lactone: isolated from mokko, Saussurea lappa; structure in first source		2.0510
lupeol
[no description available]		2.4120pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
betulonal
betulonal: originally isolated from white birch bark (Betula pendula); structure in first source		2.7130
methyl ursolate
methyl ursolate: structure in first source		2.110
sesquiterpenes
[no description available]		2.0510
betulone
[no description available]		2.0110triterpenoidmetabolite
alpha-amyrenone
alpha-amyrenone: from Marsdenia officinalis Tsiang		2.0110
beta-Elemonic acid
beta-elemonic acid: extracted from Boswellia carterii		2.0510triterpenoid
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Epidermoid
[description not available]		01.9910
Malignant Melanoma
[description not available]		01.9910
Cancer of Mouth
[description not available]		01.9910
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		01.9910
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		01.9910
Mouth Neoplasms
Tumors or cancer of the MOUTH.		01.9910
B16 Melanoma
[description not available]		02.0110
Anxiety
Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.		03.0110