Page last updated: 2024-08-05 11:53:20

pentacyclic triterpenoid

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ChEBI ID: 25872

Members (60)

MemberDefinitionRole
23-hydroxytormentic acidA pentacyclic triterpenoid that is asiatic acid substituted by a hydroxy group at position 19. It has been isolated from the leaves of Rosa laevigata.19alpha-hydroxyasiatic acid
23-hydroxyursolic acidA pentacyclic triterpenoid that is ursolic acid substituted by an additional hydroxy group at position 23. It has been isolated from Lagerstroemia speciosa and Juglans sinensis.23-hydroxyursolic acid
24-methylene cycloartanolA pentacyclic triterpenoid that is (9beta)-24-methylene-9,19-cyclolanostane which carries a hydroxy group at position 3beta. It is isolated from several plant species including Euphorbia, Epidendrum, Psychotria and Sideritis.24-methylenecycloartanol
2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acidA pentacyclic triterpenoid that is betulinic acid carrying an additional alpha-hydroxy group at position 2. It has been isolated from Breynia fruticosa.2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid
3-o-(alpha-l-arabinopyranosyl)hederageninA triterpenoid saponin that is hederagenin attached to an alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage.hederagenin 3-O-arabinoside
3-oxoglycyrrhetinic acid3-oxoglycyrrhetinic acid
7-deacetylgeduninA limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica.7-deacetylgedunin
acetyl aleuritolic acidA pentacyclic triterpenoid isolated from the leaves of Garcia parviflora.acetyl aleuritolic acid
alpha-amyrinA 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.alpha-amyrin
arjunolic acidA 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.arjunolic acid
asiatic acidA pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). It is isolated from Symplocos lancifolia and Vateria indica and exhibits anti-angiogenic activity.asiatic acid
astragaloside iiA triterpenoid saponin that is cycloastragenol glycosylated at positions 3 and 6 by 2-O-acetyl-beta-D-xylosyl and beta-D-glucosyl residues respectively.astragaloside II
astragaloside IVA pentacyclic triterpenoid that is cycloastragenol having beta-D-xylopyranosyl and beta-D-glucopyranosyl residues attached at positions O-3 and O-6 respectively. It is isolated from Astragalus membranaceus var mongholicus.astragaloside IV
bacteriohopane-32-olA pentacyclic triterpenoid that is hopane in which a hydrogen attached to C-29 is replaced by a 2-hydroxyethyl group.17beta(H),21beta(H)-bishomohopanol
beta-amyrinA 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.beta-amyrin
betulinA pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.betulin
betulinic acidA pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.betulinic acid
bevirimatA pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.bevirimat
cauloside DA triterpenoid saponin with hederagenin as the aglycone part. It has been isolated from the stem bark of Kalopanax pictus.cauloside D
celastrolA pentacyclic triterpenoid that is 24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid bearing an oxo substituent at position 2, a hydroxy substituent at position 3 and two methyl groups at positions 9 and 13. An antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF-alpha-induced NFkappaB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 muM).celastrol
cycloartenolcycloartenol
cycloeucalenoneA pentacyclic triterpenoid that is 4alpha,14-dimethyl-9beta,19-cyclo-5alpha-ergost-24(28)-ene which is substituted by an oxo group at position 3. It has been isolated from several plant species including Quercus variabilis, Ammocharis coranica, Solanum cernuum and Tinospora crispa.cycloeucalenone
cyclolaudenolA pentacyclic triterpenoid that is (24S)-methyl-9beta,19-cyclolanost-25-ene which carries a hydroxy group at position 3beta. It is isolated from several plant species inclduing Turraeanthus and Tillandsia.cyclolaudenol
cycloleucalenolcycloeucalenol
dihydrobetulinic acidA pentacyclic triterpenoid that is lupane having a 3beta-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and antileishmanial activity.dihydrobetulinic acid
diplopterolA hopanoid that is hopane substituted by a hydroxy group at position 22.hopan-22-ol
epi-maslinic acidA pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity.epi-maslinic acid
epoxyazadiradioneA limonoid that is azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes.epoxyazadiradione
erythrodiolA pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species.erythrodiol
euscaphic acidA pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata.euscaphic acid
friedelinA 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.friedelin
furostanol iA spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek.protodioscin
geduninA pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata.gedunin
glutinolA pentacyclic triterpenoid that is picene which has been fully hydrogenated except for a double bond between the 4a and 5 positions and is substituted by methyl groups at the 4, 4, 6bbeta, 8abeta, 11, 11, 12balpha and 14bbeta positions, and by a hydroxy group at the 3beta position.glutinol
glycyrrhetinic acidA pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.glycyrrhetinic acid
glycyrrhetyl 3-monoglucuronideA triterpenoid saponin that is the 3-O-beta-glucuronide of glycyrrhetic acid. It is a metabolite of glycyrrhizin contained in licorice and potentially a causative agent in the pathogenesis of pseudoaldosteronism.glycyrrhetic acid 3-O-glucuronide
glycyrrhizic acidA triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.glycyrrhizinic acid
gypsogeninA 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.gypsogenin
hederageninA sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer).hederagenin
kalopanax saponin bA triterpenoid saponin with hederagenin as the aglycone part. It has been isolated from the stem bark of Kalopanax pictus.kalopanaxsaponin B
lupeolA pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables.lupeol
madecassic acidA pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2alpha,3beta,6beta stereoisomer).madecassic acid
madecassosideA triterpenoid saponin that is a trisaccharide derivative of madecassic acid. Isolated from Centella asiatica, it exhibits anti-inflammatory, antioxidant and antirheumatic activities.madecassoside
maprounic acidA pentacyclic triterpenoid isolated from Maprounea africana and has been shown to exhibit inhibitory activity against HIV-1 reverse transcriptase.maprounic acid
maslinic acidA pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity.maslinic acid
moronic acidA pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group.moronic acid
niga-ichigoside f1A triterpenoid saponin that is 19alpha-hydroxyasiatic acid attached to a beta-D-glucopyranosyl residue at position 28 via a glycosidic linkage. It has been isolated from the leaves of Rosa laevigata.19alpha-hydroxyasiatic acid-28-O-beta-D-glucopyrannoside
oleanolic acidA pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.oleanolic acid
platanic acidA 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.platanic acid
pulsatilla saponin aA triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus.kalopanaxsaponin A
quillaic acidA pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer).quillaic acid
soyasapogenol aA pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 21beta, 22beta and 24-positions.soyasapogenol A
soyasapogenol bA pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 22beta and 24-positions.soyasapogenol B
soyasaponin bbA triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage.soyasaponin I
taraxasterolA pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3.taraxasterol
taraxerolA pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.taraxerol
tetrahymanolA pentacyclic triterpenoid having a 3beta- (21alpha-) hydroxy-substituted gammacerane structure.tetrahymanol
triptohypol CA pentacyclic triterpenoid with formula C29H40O4, originally isolated from the root bark of Tripterygium regelii.triptohypol C
triptotriterpenic acid aA pentacyclic triterpenoid with formula C30H48O4, originally isolated from Tripterygium hypoglaucum.triptotriterpenic acid A
ursolic acidA pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.ursolic acid

Research

Studies (10,503)

TimeframeStudies, Drugs in This Class (%)All Drugs %
pre-1990372 (3.54)18.7374
1990's819 (7.80)18.2507
2000's2,169 (20.65)29.6817
2010's5,118 (48.73)24.3611
2020's2,025 (19.28)2.80

Study Types

Publication TypeStudies, Drugs in This Class (%)All Drugs (%)
Trials139 (1.07%)5.53%
Reviews604 (4.65%)6.00%
Case Studies110 (0.85%)4.05%
Observational4 (0.03%)0.25%
Other12,139 (93.41%)84.16%