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16beta,17-dihydroxy-ent-kaurane-19-oic acid
A ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16beta stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity.


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07. Part of Biological Source of Chemical: plant structure [PO:0009011] > multi-tissue plant structure [PO:0025496] > fruit [PO:0009001]
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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) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antiviral agent [CHEBI:22587] (216) 
 anti-HIV agent [CHEBI:64946] (126) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Plantae (1926) 
 Magnoliophyta (1872) 
 Magnoliopsida (1649) 
 Asterales (91) 
 Asteraceae (69) 
 Helianthus (1)
 Magnoliales (39) 
 Annonaceae (35) 
 Annona (32) 
 Annona reticulata (1)
 Annona squamosa (8)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
 plant structure [PO:0009011] (1497) 
 portion of plant tissue [PO:0009007] (272) 
 epidermis [PO:0005679] (134) 
 shoot epidermis [PO:0006035] (134) 
 shoot axis epidermis [PO:0000112] (134) 
 stem epidermis [PO:0025178] (134)
 multi-tissue plant structure [PO:0025496] (1114) 
 fruit [PO:0009001] (81)
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) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 tertiary alcohol [CHEBI:26878] (183) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (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) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 tertiary alcohol [CHEBI:26878] (183) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (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) 
 diterpenoid [CHEBI:23849] (265) 
 ent-kaurane diterpenoid [CHEBI:36760] (9) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 diterpenoid [CHEBI:23849] (265) 
 ent-kaurane diterpenoid [CHEBI:36760] (9) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (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) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 tertiary alcohol [CHEBI:26878] (183) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic acid [CHEBI:64709] (3008) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 bridged compound [CHEBI:35990] (118) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (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) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 polyol [CHEBI:26191] (437) 
 diol [CHEBI:23824] (172) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
 tertiary alcohol [CHEBI:26878] (183) 
 16beta,17-dihydroxy-ent-kaurane-19-oic acid [CHEBI:65778] (1)
ChEBI Compound Accession Identifier  [CHEBI:65778]
ChEBI Compound Description  A ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16beta stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity.
ChEBI Compound Identification Number  65778
ChEBI InChI Value  InChI=1S/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13?,14-,15-,17+,18+,19-,20+/m0/s1
ChEBI InChIKey Value  MRBLTWPEPGRXQN-VCFJOFAESA-N
ChEBI Compound Name  16beta,17-dihydroxy-ent-kaurane-19-oic acid
ChEBI SMILES Value  [H][C@]12CC[C@@]34C[C@@H](CC[C@@]3([H])[C@]1(C)CCC[C@@]2(C)C(O)=O)[C@](O)(CO)C4
ChEBI Substance ID  160709544
ChEBI URL  ChEBI:65778
ChemSpider ID  412200
Ontomatica Chemical Accession Key (OnChAKey)  MRBLTWPEPGRXQN_VCFJOFAESA_N_000_000000
PubChem Compound ID  469209