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3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of trans-4-coumaric acid with D:C-friedoolean-7,9(11)-dien-3beta-ol-29-oic acid. It is isolated from the stems of Lagenaria siceraria and exhibits cytotoxic activity against human hepatoma SK-Hep 1 cells.

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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619]
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05. Industrial Uses: pharmaceutical [CHEBI:52217]
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more general categories    information about this item
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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antineoplastic agent [CHEBI:35610] (760) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Plantae (1926) 
 Magnoliophyta (1872) 
 Magnoliopsida (1649) 
 Cucurbitales (4) 
 Cucurbitaceae (4) 
 Lagenaria (2) 
 Lagenaria siceraria (2)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 plant structure [PO:0009011] (1497) 
 multi-tissue plant structure [PO:0025496] (1114) 
 plant organ [PO:0009008] (970) 
 plant axis [PO:0025004] (691) 
 shoot axis [PO:0025029] (271) 
 stem [PO:0009047] (170)
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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 triterpenoid [CHEBI:36615] (228) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 ester [CHEBI:35701] (3370) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic acid [CHEBI:64709] (3008) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenylpropanoid [CHEBI:26004] (374) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 pentacyclic triterpenoid [CHEBI:25872] (112) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 alpha,beta-unsaturated carboxylic ester [CHEBI:51737] (68) 
 enoate ester [CHEBI:51702] (65) 
 cinnamate ester [CHEBI:36087] (36) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (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) 
 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid [CHEBI:65663] (1)
ChEBI Compound Accession Identifier:   [CHEBI:65663]
ChEBI Compound Description:   A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of trans-4-coumaric acid with D:C-friedoolean-7,9(11)-dien-3beta-ol-29-oic acid. It is isolated from the stems of Lagenaria siceraria and exhibits cytotoxic activity against human hepatoma SK-Hep 1 cells.
ChEBI Compound Identification Number:   65663
ChEBI InChI Value:   InChI=1S/C39H52O5/c1-34(2)29-14-13-28-27(37(29,5)18-17-31(34)44-32(41)15-10-25-8-11-26(40)12-9-25)16-19-39(7)30-24-36(4,33(42)43)21-20-35(30,3)22-23-38(28,39)6/h8-13,15-16,29-31,40H,14,17-24H2,1-7H3,(H,42,43)/b15-10+/t29-,30+,31-,35+,36+,37+,38+,39-/m0/s1
ChEBI InChIKey Value:   NOTQCQMXZCILJE-WYGBHMDXSA-N
ChEBI Compound Name:   3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
ChEBI SMILES Value:   [H][C@@]12CC=C3C(=CC[C@@]4(C)[C@]5([H])C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(O)=O)[C@@]1(C)CC[C@H](OC(=O)\C=C\c1ccc(O)cc1)C2(C)C
ChEBI Substance ID:   160655782
ChEBI URL:   ChEBI:65663
ChemSpider ID:   28532956
Ontomatica Chemical Accession Key (OnChAKey):   NOTQCQMXZCILJE_WYGBHMDXSA_N_000_000000
PubChem Compound ID:   24850702