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2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid
A pentacyclic triterpenoid that is urs-12-ene substituted by a carboxy group at position 28, alpha-configured hydroxy groups at positions 2 and 19 and an oxo group at position 3. Isolated from the whole plants of Geum japonicum, it exhibits activity against HIV-1 protease.


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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281] > antiviral agent [CHEBI:22587] > anti-HIV agent [CHEBI:64946] > HIV protease inhibitor [CHEBI:35660] > 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antiviral agent [CHEBI:22587] (216) 
 anti-HIV agent [CHEBI:64946] (126) 
 HIV protease inhibitor [CHEBI:35660] (14) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 lipid [CHEBI:18059] (3532) 
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 triterpenoid [CHEBI:36615] (228) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 triterpenoid [CHEBI:36615] (228) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic acid [CHEBI:64709] (3008) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 oxo carboxylic acid [CHEBI:25754] (273) 
 oxo monocarboxylic acid [CHEBI:35871] (198) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid [CHEBI:65783] (1)
ChEBI Compound Accession Identifier  [CHEBI:65783]
ChEBI Compound Description  A pentacyclic triterpenoid that is urs-12-ene substituted by a carboxy group at position 28, alpha-configured hydroxy groups at positions 2 and 19 and an oxo group at position 3. Isolated from the whole plants of Geum japonicum, it exhibits activity against HIV-1 protease.
ChEBI Compound Identification Number  65783
ChEBI InChI Value  InChI=1S/C30H46O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-22,31,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1
ChEBI InChIKey Value  LJORXTIGOHMBOS-OTRVPSFMSA-N
ChEBI Compound Name  2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid
ChEBI SMILES Value  [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)C(=O)C2(C)C
ChEBI Substance ID  160709528
ChEBI URL  ChEBI:65783
ChemSpider ID  552868
Ontomatica Chemical Accession Key (OnChAKey)  LJORXTIGOHMBOS_OTRVPSFMSA_N_000_000000
PubChem Compound ID  637229