phorbol 13-acetate 12-myristate (CHEBI:37537)

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CHEBI:37537 - phorbol 13-acetate 12-myristate

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ChEBI ID	CHEBI:37537
ChEBI Name	phorbol 13-acetate 12-myristate
Stars
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.
Secondary ChEBI IDs	CHEBI:745, CHEBI:746
Last Modified	28 May 2024
Submitter	Kirill Degtyarenko
Downloads	Molfile

Formula	C36H56O8
Net Charge	0
Average Mass	616.836
Monoisotopic Mass	616.39752
SMILES	[H][C@@]12C=C(C)C(=O)[C@@]1(O)CC(CO)=C[C@]1([H])[C@]2(O)[C@H](C)[C@@H](OC(=O)CCCCCCCCCCCCC)[C@@]2(OC(C)=O)C(C)(C)[C@@]12[H]
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Croton tiglium (ncbitaxon:497687)	seed (BTO:0001226)	PubMed (32640883)	Isolated from seed oil.

Roles Classification

Chemical Role:	reactive oxygen species generator Any entity used to generate reactive oxygen species.
Biological Roles:	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. 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. 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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
12-O-tetradecanoylphorbol 13-acetate	KEGG COMPOUND
phorbol 12-myristate 13-acetate	KEGG COMPOUND
12-tetradecanoylphorbol 13-acetate	KEGG COMPOUND
tetradecanoylphorbol acetate	ChemIDplus
PMA	ChemIDplus
phorbol 12-tetradecanoate 13-acetate	ChemIDplus

Manual Xrefs	Databases
C05151	KEGG COMPOUND
C00003491	KNApSAcK
12-O-Tetradecanoylphorbol-13-acetate	Wikipedia
LSM-25630	LINCS
LMPR0104330002	LIPID MAPS
CPD-19636	MetaCyc
25977	ChemSpider
HMDB0244744	HMDB

Registry Numbers	Sources
Beilstein:2407201	Beilstein
CAS:16561-29-8	KEGG COMPOUND
CAS:16561-29-8	KEGG COMPOUND
CAS:16561-29-8	ChemIDplus

Citations