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 to the corresponding acetate and myristate esters.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:746, CHEBI:745
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Formula C36H56O8
Net Charge 0
Average Mass 616.826
Monoisotopic Mass 616.398
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]
Roles Classification
Biological Role(s): protein kinase C agonist
An agonist that selectively binds to and activates a protein kinase C receptor
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 protein kinase C agonist (CHEBI:64018)
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 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
Database Links Databases
12-O-Tetradecanoylphorbol-13-acetate Wikipedia
C00003491 KNApSAcK
C05151 KEGG COMPOUND
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Registry Numbers Types Sources
16561-29-8 CAS Registry Number ChemIDplus
2407201 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18541361 PubMed citation Europe PMC
22696070 PubMed citation Europe PMC
25649981 PubMed citation Europe PMC
25918710 PubMed citation Europe PMC
26826276 PubMed citation Europe PMC
26894087 PubMed citation Europe PMC
3593207 PubMed citation Europe PMC
Last Modified
04 May 2016