CHEBI:37537 - phorbol 13-acetate 12-myristate

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ChEBI Name phorbol 13-acetate 12-myristate
ChEBI ID CHEBI:37537
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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:746, CHEBI:745
Supplier Information ChemicalBook:CB2185552, ZINC000008215481
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Guanosine diphosphate, abbreviated GDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of a pyrophosphate group, a pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g., the G-proteins that are involved in signal transduction. GDP is converted into GTP with the help of pyruvate kinase and phosphoenolpyruvate.
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Formula C36H56O8
Net Charge 0
Average Mass 616.826
Monoisotopic Mass 616.39752
InChI 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
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]
Metabolite of Species Details
Croton tiglium (NCBI:txid497687) Found in seed (BTO:0001226). Isolated from seed oil. See: PubMed
Roles Classification
Chemical Role(s): reactive oxygen species generator
Any entity used to generate reactive oxygen species.
Biological Role(s): protein kinase C agonist
An agonist that selectively binds to and activates a protein kinase C receptor
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mitogen
A chemical substance that encourages a cell to commence cell division, triggering mitosis.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phorbol 13-acetate 12-myristate (CHEBI:37537) has role antineoplastic agent (CHEBI:35610)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role apoptosis inducer (CHEBI:68495)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role carcinogenic agent (CHEBI:50903)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role mitogen (CHEBI:52290)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role plant metabolite (CHEBI:76924)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role protein kinase C agonist (CHEBI:64018)
phorbol 13-acetate 12-myristate (CHEBI:37537) has role reactive oxygen species generator (CHEBI:70982)
phorbol 13-acetate 12-myristate (CHEBI:37537) is a acetate ester (CHEBI:47622)
phorbol 13-acetate 12-myristate (CHEBI:37537) is a diester (CHEBI:51307)
phorbol 13-acetate 12-myristate (CHEBI:37537) is a phorbol ester (CHEBI:37532)
phorbol 13-acetate 12-myristate (CHEBI:37537) is a tertiary α-hydroxy ketone (CHEBI:139592)
phorbol 13-acetate 12-myristate (CHEBI:37537) is a tetradecanoate ester (CHEBI:87691)
IUPAC Name
(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
Synonyms Sources
12-O-tetradecanoylphorbol 13-acetate KEGG COMPOUND
12-tetradecanoylphorbol 13-acetate KEGG COMPOUND
phorbol 12-myristate 13-acetate KEGG COMPOUND
phorbol 12-tetradecanoate 13-acetate ChemIDplus
phorbol-12-myristate-13-acetate ChEBI
PMA ChemIDplus
tetradecanoylphorbol acetate ChemIDplus
TPA ChEBI
Manual Xrefs Databases
12-O-Tetradecanoylphorbol-13-acetate Wikipedia
25977 ChemSpider
C00003491 KNApSAcK
C05151 KEGG COMPOUND
CPD-19636 MetaCyc
HMDB0244744 HMDB
LMPR0104330002 LIPID MAPS
LSM-25630 LINCS
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Registry Numbers Types Sources
16561-29-8 CAS Registry Number ChemIDplus
2407201 Beilstein Registry Number ChemIDplus
Citations Types Sources
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Last Modified
28 May 2024