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2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
A pentacyclic triterpenoid that is the diester obtained by the condensation of the hydroxy groups of 2alpha-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits inhibitory activity against HIV-1 reverse transcriptase.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672]
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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-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antiviral agent [CHEBI:22587] (216) 
 anti-HIV agent [CHEBI:64946] (126) 
 anti-HIV-1 agent [CHEBI:64947] (79) 
 HIV-1 reverse transcriptase inhibitor [CHEBI:53756] (30) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (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-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 triterpenoid [CHEBI:36615] (228) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 ester [CHEBI:35701] (3370) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 aromatic ester [CHEBI:62732] (94) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (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-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 aromatic compound [CHEBI:33655] (3799) 
 aromatic ester [CHEBI:62732] (94) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 benzoate ester [CHEBI:36054] (83) 
 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate [CHEBI:66672] (1)
ChEBI Compound Accession Identifier  [CHEBI:66672]
ChEBI Compound Description  A pentacyclic triterpenoid that is the diester obtained by the condensation of the hydroxy groups of 2alpha-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits inhibitory activity against HIV-1 reverse transcriptase.
ChEBI Compound Identification Number  66672
ChEBI InChI Value  InChI=1S/C44H56O8/c1-39(2)22-23-44(38(49)50)21-18-32-41(5)19-16-31-40(3,4)35(52-37(48)27-10-14-29(46)15-11-27)30(51-36(47)26-8-12-28(45)13-9-26)24-43(31,7)33(41)17-20-42(32,6)34(44)25-39/h8-15,18,30-31,33-35,45-46H,16-17,19-25H2,1-7H3,(H,49,50)/t30-,31+,33+,34+,35+,41+,42-,43+,44-/m1/s1
ChEBI InChIKey Value  XPEVLOSUULAUFH-AHHVVZNJSA-N
ChEBI Compound Name  2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
ChEBI SMILES Value  [H][C@@]12CC[C@@]3(C)C4=CC[C@]5(CCC(C)(C)C[C@@]5([H])[C@]4(C)CC[C@]3([H])[C@@]1(C)C[C@@H](OC(=O)c1ccc(O)cc1)[C@H](OC(=O)c1ccc(O)cc1)C2(C)C)C(O)=O
ChEBI Substance ID  160710322
ChEBI URL  ChEBI:66672
ChemSpider ID  NS
Ontomatica Chemical Accession Key (OnChAKey)  XPEVLOSUULAUFH_AHHVVZNJSA_N_000_000000
PubChem Compound ID  3081904