CHEBI ONTOLOGY - ANNOTATIONS
The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/ . The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/ ). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term: phorbol 13-acetate 12-myristate
Accession: CHEBI:37537
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Definition: A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.
Synonyms: exact_synonym: (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate
related_synonym: 12-O-tetradecanoylphorbol 13-acetate; 12-tetradecanoylphorbol 13-acetate; Formula=C36H56O8; InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1; InChIKey=PHEDXBVPIONUQT-RGYGYFBISA-N; PMA; SMILES=C=1[C@]2([C@]3([C@@]([C@H](OC(=O)CCCCCCCCCCCCC)[C@H]([C@@]2([C@]4([C@@](C(=O)C(=C4)C)(CC1CO)O)[H])O)C)(C3(C)C)OC(=O)C)[H])[H]; TPA; phorbol 12-tetradecanoate 13-acetate; tetradecanoylphorbol acetate
alt_id: CHEBI:745; CHEBI:746
xref: Beilstein:2407201; CAS:16561-29-8; Chemspider:25977; KEGG:C05151; KEGG:C09199; KNApSAcK:C00003491; LINCS:LSM-25630; LIPID_MAPS_instance:LMPR0104330002
xref_mesh: MESH:D013755
xref: MetaCyc:CPD-19636; PMCID:PMC6898309; PMID:12421969; PMID:15721302; PMID:15822940; PMID:16740769; PMID:18541361; PMID:20333698; PMID:22696070; PMID:25649981; PMID:25918710; PMID:26826276; PMID:26894087; PMID:27315825; PMID:27676154; PMID:2866623; PMID:29291631; PMID:29385060; PMID:29538403; PMID:29872754; PMID:29933732; PMID:30075941; PMID:30248704; PMID:30254419; PMID:30663866; PMID:31019367; PMID:31194000; PMID:31256364; PMID:31437790; PMID:31904021; PMID:32140039; PMID:33254440; PMID:33268675; PMID:33291656; PMID:34234780; PMID:3593207; Wikipedia:12-O-Tetradecanoylphorbol-13-acetate
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CXCL8
C-X-C motif chemokine ligand 8
multiple interactions
EXP
[Tetradecanoylphorbol Acetate co-treated with Ionomycin] results in increased secretion of CXCL8 protein
CTD
PMID:15912099
NCBI chr 8:69,932,646...69,935,861
Ensembl chr 8:69,932,643...69,935,861
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EDN1
endothelin 1
multiple interactions increases expression
EXP
Clofibrate inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of EDN1 protein]
CTD
PMID:17105827
NCBI chr 7:8,752,018...8,758,354
Ensembl chr 7:8,751,695...8,758,348
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MAPK1
mitogen-activated protein kinase 1
increases phosphorylation
EXP
Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK1 protein
CTD
PMID:11325585
NCBI chr14:50,083,079...50,165,528
Ensembl chr14:50,082,896...50,165,513
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MAPK3
mitogen-activated protein kinase 3
increases phosphorylation
EXP
Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK3 protein
CTD
PMID:11325585
NCBI chr 3:18,291,444...18,299,410
Ensembl chr 3:18,291,445...18,299,567
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MAPK9
mitogen-activated protein kinase 9
increases phosphorylation
EXP
Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK9 protein
CTD
PMID:11325585
NCBI chr 2:78,338,466...78,399,108
Ensembl chr 2:78,338,376...78,399,100
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PPARA
peroxisome proliferator activated receptor alpha
decreases expression multiple interactions
EXP
Tetradecanoylphorbol Acetate results in decreased expression of PPARA; Tetradecanoylphorbol Acetate results in decreased expression of PPARA protein calphostin C promotes the reaction [Tetradecanoylphorbol Acetate results in decreased expression of PPARA]; Tetradecanoylphorbol Acetate inhibits the reaction [Clofibrate results in increased expression of PPARA]
CTD
PMID:17105827 PMID:20568414
NCBI chr 5:3,302,755...3,321,091
Ensembl chr 5:3,300,741...3,364,239
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PRKCB
protein kinase C beta
decreases phosphorylation
EXP
Tetradecanoylphorbol Acetate results in decreased phosphorylation of PRKCB protein
CTD
PMID:15089098
NCBI chr 3:21,995,227...22,383,628
Ensembl chr 3:21,995,231...22,383,264
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PRKCD
protein kinase C delta
increases phosphorylation
EXP
Tetradecanoylphorbol Acetate results in increased phosphorylation of PRKCD protein
CTD
PMID:15089098
NCBI chr13:35,290,835...35,323,245
Ensembl chr13:35,290,610...35,323,356
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SELE
selectin E
increases expression
EXP
Tetradecanoylphorbol Acetate results in increased expression of SELE protein
CTD
PMID:16797888
NCBI chr 4:81,289,061...81,299,657
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SELP
selectin P
increases expression
EXP
Tetradecanoylphorbol Acetate results in increased expression of SELP protein
CTD
PMID:16797888
NCBI chr 4:81,376,804...81,401,240
Ensembl chr 4:81,365,740...81,399,955
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VCAM1
vascular cell adhesion molecule 1
increases expression
EXP
Tetradecanoylphorbol Acetate results in increased expression of VCAM1 protein
CTD
PMID:16797888
NCBI chr 4:117,496,914...117,511,211
Ensembl chr 4:117,496,920...117,511,222
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