Literature summary for 2.4.1.1 extracted from

Liang, Z.; Zhang, L.; Li, L.; Liu, J.; Li, H.; Zhang, L.; Chen, L.; Cheng, K.; Zheng, M.; Wen, X.; Zhang, P.; Hao, J.; Gong, Y.; Zhang, X.; Zhu, X.; Chen, J.; Liu, H.; Jiang, H.; Luo, C.; Sun, H.
Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies (2011), Eur. J. Med. Chem., 46, 2011-2021.

Application

Application	Comment	Organism
drug development	pentacyclic triterpenes, as inhibitors of glycogen phosphorylase, hold promise for the treatment of type-2 diabetes and other diseases with disorders in glycogen metabolism	Oryctolagus cuniculus

Inhibitors

Inhibitors	Comment	Organism
(2alpha)-3-hydroxyolean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2alpha,3beta)-2,3-bis(acetyloxy)olean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2alpha,3beta)-2,3-bis(butanoyloxy)olean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2alpha,3beta)-2,3-bis(propanoyloxy)olean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2beta)-2-hydroxyurs-12-en-28-oic acid	-	Oryctolagus cuniculus
(2beta)-3-hydroxyolean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2beta,3alpha)-2,3-dihydroxyolean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2beta,3alpha)-2,3-dihydroxyurs-12-en-28-oic acid	-	Oryctolagus cuniculus
(2Z)-2-(hydroxyimino)olean-12-en-28-oic acid	-	Oryctolagus cuniculus
(2Z)-2-(hydroxyimino)urs-12-en-28-oic acid	-	Oryctolagus cuniculus
(3beta)-28-[(2-[[2-(acetylamino)ethyl]amino]ethyl)amino]-28-oxoolean-12-en-3-yl acetate	-	Oryctolagus cuniculus
(3beta)-3-[[(4-[[(phenylacetyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)acetyl]oxy]olean-12-en-28-oic acid	-	Oryctolagus cuniculus
(3beta,12alpha,13xi)-3,12-dihydroxyoleanan-28-oic acid	-	Oryctolagus cuniculus
(3beta,3'beta)-3,3'-[hexane-1,6-diylbis(1H-1,2,3-triazole-1,4-diylmethanediyloxy)]bisolean-12-en-28-oic acid	-	Oryctolagus cuniculus
(4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinoxaline-4a(2H)-carboxylic acid	-	Oryctolagus cuniculus
(6aS,6bR,8aR,16aR,16bR,18bS)-2,2,6a,6b,9,9,16a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,16,16a,16b,17,18b-hexadecahydrochryseno[1,2-b]phenazine-4a(2H)-carboxylic acid	-	Oryctolagus cuniculus
1-[6-(acetyloxy)hexyl] 4-(7-[[(3beta)-3-hydroxy-28-oxoolean-12-en-28-yl]oxy]heptyl) (2R)-2-hydroxybutanedioate	-	Oryctolagus cuniculus
2,3,4,6-tetra-O-acetyl-1-O-[(2alpha,3beta)-2,3-dihydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose	-	Oryctolagus cuniculus
2-(phenylamino)ethyl (3beta)-3-hydroxyurs-12-en-28-oate	-	Oryctolagus cuniculus
2-bromoethyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
2-bromoethyl (3beta)-3-hydroxyurs-12-en-28-oate	-	Oryctolagus cuniculus
2-ethoxy-2-oxoethyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
2-oxours-12-en-28-oic acid	-	Oryctolagus cuniculus
2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate	-	Oryctolagus cuniculus
2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate	-	Oryctolagus cuniculus
6-(butylamino)hexyl (3beta)-3-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
6-aminohexyl (3beta)-3-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
6-[(4-methylphenyl)amino]hexyl (3beta)-3-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2beta)-2-hydroxyurs-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2beta,3alpha)-2,3-dihydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2beta,3alpha)-2,3-dihydroxyurs-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2Z)-2-(hydroxyimino)olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (2Z)-2-(hydroxyimino)urs-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (3beta)-3-[(pyridinium-1-ylacetyl)oxy]olean-12-en-28-oate chloride	-	Oryctolagus cuniculus
benzyl (3beta)-3-[([4-[(4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl]phenoxy)methyl]-1H-1,2,3-triazol-1-yl]acetyl)oxy]olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (3beta)-3-[([4-[(dodecanoyloxy)methyl]-1H-1,2,3-triazol-1-yl]acetyl)oxy]olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (3beta)-3-[[(4-[[(phenylacetyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)acetyl]oxy]olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl (3beta,12alpha,13xi)-3,12-dihydroxyoleanan-28-oate	-	Oryctolagus cuniculus
benzyl (3beta,12beta,13xi)-3,12-dihydroxyoleanan-28-oate	-	Oryctolagus cuniculus
benzyl 2-oxoolean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 2-oxours-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 3beta-(2-(diethylamino)acetoxy)olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 3beta-(2-azidoacetoxy)olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 3beta-(2-chloroacetoxy)olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 3beta-(4-aminobenzoyloxy)olean-12-en-28-oate	-	Oryctolagus cuniculus
benzyl 3beta-(4-nitrobenzoyloxy)olean-12-en-28-oate	-	Oryctolagus cuniculus
butyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
ethyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
methyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
methyl (2S)-[[(2alpha,3beta)-2,3-bis(acetyloxy)-28-oxours-12-en-28-yl]amino](4-hydroxyphenyl)ethanoate	-	Oryctolagus cuniculus
methyl (2S)-[[(2alpha,3beta)-2,3-bis(acetyloxy)-28-oxours-12-en-28-yl]amino](phenyl)ethanoate	-	Oryctolagus cuniculus
methyl 6-deoxy-6-[4-([[(3beta)-3-hydroxy-28-oxoolean-12-en-28-yl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-alpha-D-glucopyranoside	-	Oryctolagus cuniculus
additional information	evaluation of pentacyclic triterpenes as a class of inhibitors against glycogen phosphorylase, by receptor-based comparative molecular field analysis, and comparative molecular similarity analysis to investigate the quantitative structure-activity relationships of 106 compounds, detailed overview	Oryctolagus cuniculus
prop-2-en-1-yl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
propyl (2beta)-2-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus
[1-(6-[4-[(acetyloxy)methyl]-1H-1,2,3-triazol-1-yl]hexyl)-1H-1,2,3-triazol-4-yl]methyl (3b)-3-hydroxyolean-12-en-28-oate	-	Oryctolagus cuniculus

Metals/Ions

Metals/Ions	Comment	Organism	Structure
Mg2+	activates	Oryctolagus cuniculus

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
[(1->4)-alpha-D-glucosyl]n + phosphate	Oryctolagus cuniculus	-	[(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate	-	r

Organism

Organism	UniProt	Comment	Textmining
Oryctolagus cuniculus	-	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
[(1->4)-alpha-D-glucosyl]n + phosphate	-	Oryctolagus cuniculus	[(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate	-	r

Subunits

Subunits	Comment	Organism
dimer	-	Oryctolagus cuniculus

Synonyms

Synonyms	Comment	Organism
glycogen phosphorylase	-	Oryctolagus cuniculus
GPb	-	Oryctolagus cuniculus

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
22	-	assay at	Oryctolagus cuniculus

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7.2	-	assay at	Oryctolagus cuniculus

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
additional information	-	kinetics of inhibition of the forward reaction	Oryctolagus cuniculus	additional information
0.0011	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2beta,3alpha)-2,3-dihydroxyurs-12-en-28-oic acid
0.00114	-	pH 7.2, 22°C	Oryctolagus cuniculus	methyl 6-deoxy-6-[4-([[(3beta)-3-hydroxy-28-oxoolean-12-en-28-yl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-alpha-D-glucopyranoside
0.00125	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2beta,3alpha)-2,3-dihydroxyurs-12-en-28-oate
0.00153	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
0.00213	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 3beta-(4-aminobenzoyloxy)olean-12-en-28-oate
0.00223	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
0.0026	-	pH 7.2, 22°C	Oryctolagus cuniculus	(3beta,3'beta)-3,3'-[hexane-1,6-diylbis(1H-1,2,3-triazole-1,4-diylmethanediyloxy)]bisolean-12-en-28-oic acid
0.0031	-	pH 7.2, 22°C	Oryctolagus cuniculus	(3beta,12alpha,13xi)-3,12-dihydroxyoleanan-28-oic acid
0.0032	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 2-oxoolean-12-en-28-oate
0.00325	-	pH 7.2, 22°C	Oryctolagus cuniculus	(3beta)-28-[(2-[[2-(acetylamino)ethyl]amino]ethyl)amino]-28-oxoolean-12-en-3-yl acetate
0.0042	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2beta)-2-hydroxyolean-12-en-28-oate
0.00535	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta,12beta,13xi)-3,12-dihydroxyoleanan-28-oate
0.00539	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta)-3-[(pyridinium-1-ylacetyl)oxy]olean-12-en-28-oate chloride
0.00625	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2beta,3alpha)-2,3-dihydroxyolean-12-en-28-oic acid
0.0065	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta,12alpha,13xi)-3,12-dihydroxyoleanan-28-oate
0.00669	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2beta,3alpha)-2,3-dihydroxyolean-12-en-28-oate
0.0078	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta)-3-[([4-[(dodecanoyloxy)methyl]-1H-1,2,3-triazol-1-yl]acetyl)oxy]olean-12-en-28-oate
0.01025	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-bromoethyl (3beta)-3-hydroxyurs-12-en-28-oate
0.0105	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2alpha,3beta)-2,3-bis(propanoyloxy)olean-12-en-28-oic acid
0.0112	-	pH 7.2, 22°C	Oryctolagus cuniculus	methyl (2S)-[[(2alpha,3beta)-2,3-bis(acetyloxy)-28-oxours-12-en-28-yl]amino](4-hydroxyphenyl)ethanoate
0.0123	-	pH 7.2, 22°C	Oryctolagus cuniculus	1-[6-(acetyloxy)hexyl] 4-(7-[[(3beta)-3-hydroxy-28-oxoolean-12-en-28-yl]oxy]heptyl) (2R)-2-hydroxybutanedioate
0.0126	-	pH 7.2, 22°C	Oryctolagus cuniculus	6-(butylamino)hexyl (3beta)-3-hydroxyolean-12-en-28-oate
0.0126	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 3beta-(2-chloroacetoxy)olean-12-en-28-oate
0.0127	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 3beta-(2-azidoacetoxy)olean-12-en-28-oate
0.0131	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2Z)-2-(hydroxyimino)olean-12-en-28-oic acid
0.0133	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2alpha,3beta)-2,3-bis(acetyloxy)olean-12-en-28-oic acid
0.0138	-	pH 7.2, 22°C	Oryctolagus cuniculus	butyl (2beta)-2-hydroxyolean-12-en-28-oate
0.014	-	pH 7.2, 22°C	Oryctolagus cuniculus	(6aS,6bR,8aR,16aR,16bR,18bS)-2,2,6a,6b,9,9,16a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,16,16a,16b,17,18b-hexadecahydrochryseno[1,2-b]phenazine-4a(2H)-carboxylic acid
0.0141	-	pH 7.2, 22°C	Oryctolagus cuniculus	6-aminohexyl (3beta)-3-hydroxyolean-12-en-28-oate
0.0147	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2Z)-2-(hydroxyimino)urs-12-en-28-oic acid
0.0153	-	pH 7.2, 22°C	Oryctolagus cuniculus	ethyl (2beta)-2-hydroxyolean-12-en-28-oate
0.0161	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 3beta-(4-nitrobenzoyloxy)olean-12-en-28-oate
0.0161	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2alpha)-3-hydroxyolean-12-en-28-oic acid
0.0163	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2Z)-2-(hydroxyimino)olean-12-en-28-oate
0.0175	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta)-3-[([4-[(4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl]phenoxy)methyl]-1H-1,2,3-triazol-1-yl]acetyl)oxy]olean-12-en-28-oate
0.0186	-	pH 7.2, 22°C	Oryctolagus cuniculus	2,3,4,6-tetra-O-acetyl-1-O-[(2alpha,3beta)-2,3-dihydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose
0.0201	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 3beta-(2-(diethylamino)acetoxy)olean-12-en-28-oate
0.0202	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2Z)-2-(hydroxyimino)urs-12-en-28-oate
0.0206	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2beta)-2-hydroxyurs-12-en-28-oic acid
0.0207	-	pH 7.2, 22°C	Oryctolagus cuniculus	[1-(6-[4-[(acetyloxy)methyl]-1H-1,2,3-triazol-1-yl]hexyl)-1H-1,2,3-triazol-4-yl]methyl (3b)-3-hydroxyolean-12-en-28-oate
0.0223	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (2beta)-2-hydroxyurs-12-en-28-oate
0.0225	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-ethoxy-2-oxoethyl (2beta)-2-hydroxyolean-12-en-28-oate
0.0227	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2beta)-3-hydroxyolean-12-en-28-oic acid
0.0231	-	pH 7.2, 22°C	Oryctolagus cuniculus	prop-2-en-1-yl (2beta)-2-hydroxyolean-12-en-28-oate
0.0239	-	pH 7.2, 22°C	Oryctolagus cuniculus	methyl (2S)-[[(2alpha,3beta)-2,3-bis(acetyloxy)-28-oxours-12-en-28-yl]amino](phenyl)ethanoate
0.0242	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl 2-oxours-12-en-28-oate
0.0251	-	pH 7.2, 22°C	Oryctolagus cuniculus	(4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinoxaline-4a(2H)-carboxylic acid
0.0252	-	pH 7.2, 22°C	Oryctolagus cuniculus	(2alpha,3beta)-2,3-bis(butanoyloxy)olean-12-en-28-oic acid
0.0254	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-bromoethyl (2beta)-2-hydroxyolean-12-en-28-oate
0.0256	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-(phenylamino)ethyl (3beta)-3-hydroxyurs-12-en-28-oate
0.0273	-	pH 7.2, 22°C	Oryctolagus cuniculus	propyl (2beta)-2-hydroxyolean-12-en-28-oate
0.0277	-	pH 7.2, 22°C	Oryctolagus cuniculus	benzyl (3beta)-3-[[(4-[[(phenylacetyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)acetyl]oxy]olean-12-en-28-oate
0.0281	-	pH 7.2, 22°C	Oryctolagus cuniculus	methyl (2beta)-2-hydroxyolean-12-en-28-oate
0.0281	-	pH 7.2, 22°C	Oryctolagus cuniculus	6-[(4-methylphenyl)amino]hexyl (3beta)-3-hydroxyolean-12-en-28-oate
0.029	-	pH 7.2, 22°C	Oryctolagus cuniculus	2-oxours-12-en-28-oic acid
0.0309	-	pH 7.2, 22°C	Oryctolagus cuniculus	(3beta)-3-[[(4-[[(phenylacetyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)acetyl]oxy]olean-12-en-28-oic acid