ChemSpider 2D Image | 12-O-Tetradecanoylphorbol-13-acetate | C36H56O8

12-O-Tetradecanoylphorbol-13-acetate

  • Molecular FormulaC36H56O8
  • Average mass616.825 Da
  • Monoisotopic mass616.397522 Da
  • ChemSpider ID25977

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-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
(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 myristate [ACD/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-ylmyristat [German] [ACD/IUPAC Name]
(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,?.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate
12-O-Tetradecanoylphorbol 13-acetate
12-O-Tetradecanoylphorbol-13-acetate [Wiki]
16561-29-8 [RN]
2407201 [Beilstein]
4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
4β-Phorbol 12-myristate 13-acetate
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

79346_FLUKA [DBID]
79350_FLUKA [DBID]
AIDS000741 [DBID]
AIDS-000741 [DBID]
Bio1_000300 [DBID]
Bio1_000789 [DBID]
Bio1_001278 [DBID]
Bio2_000352 [DBID]
Bio2_000832 [DBID]
BRN 2407201 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      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 c ell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types. ChEBI CHEBI:37537
      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 my ristate esters. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:37537, CHEBI:37537

    • Bio Activity:

      <p>Phorbol 12-myristate 13-acetate (PMA) is a protein kinase C (PKC) activator which associates to the C1 domain. It is structurally analogous to diacylglycerol and has various biological actions. It induces ERK1/2 activation.</p> <p>It is widely used to differentiate THP-1 cells for use as a model for function and biology of human macrophages.</p> <p><br/>It is frequently used with <a href="/ionomycin-calcium-salt.html" title="Ionomycin| Stimulates cytokine production | Hello Bio" target="_self">ionomycin</a> to stimulate intracellular cytokine production in T-cells. Also used with Concanavalin A (ConA) to stimulate DNA and protein synthesis.</p> <p><br/>PMA also facilitates long term potentiation in hippocampal neurons via &delta; and &epsilon; PKC binding sites.</p> <p><br/>Additionally, PMA potentiates exocytosis and modulates vesicle fusion kinetics.</p> <p><br/>It is a potent tumor promoter.</p> Hello Bio HB0502
      <p>Phorbol 12-myristate 13-acetate (PMA) is a protein kinase C (PKC) activator which associates to the C1 domain. It is structurally analogous to diacylglycerol.</p> <p><br/>PMA is a potent tumor promoter.</p> <p><br/>PMA induces ERK1/2 activation and is frequently used with <a href=/ionomycin-calcium-salt.html title=Ionomycin| Stimulates cytokine production | Hello Bio target=_self>ionomycin</a> to stimulate intracellular cytokine production in T-cells.</p> <p><br/>PMA also facilitates long term potentiation in hippocampal neurons via &delta; and &epsilon; PKC binding sites.</p> <p><br/>Additionally, PMA potentiates exocytosis and modulates vesicle fusion kinetics.</p> Hello Bio HB0502
      Biochemicals & small molecules/Agonists & activators Hello Bio HB0502
      Enzymes Tocris Bioscience 1201
      Enzymes/Kinase/PKC Hello Bio HB0502
      Enzymes/Kinase/Protein-serine/threonine kinase/General Hello Bio HB0502
      Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a Ki value of 2.6 nM as measured by displacement of [3H]phorbol 12,13-dibutyrate binding in rat cortex s ynaptosomal membranes. Tocris Bioscience 1201
      Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a Ki value of 2.6 nM as measured by displacement of [3H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes. Tocris Bioscience 1201
      Kinases Tocris Bioscience 1201
      PKC activator Hello Bio HB0502
      Protein Kinase C Tocris Bioscience 1201
      Protein kinase C activator Tocris Bioscience 1201

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 698.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.0 mmHg at 25°C
Enthalpy of Vaporization: 116.9±6.0 kJ/mol
Flash Point: 208.1±25.0 °C
Index of Refraction: 1.553
Molar Refractivity: 168.3±0.4 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 17
#Rule of 5 Violations: 2
ACD/LogP: 7.71
ACD/LogD (pH 5.5): 8.08
ACD/BCF (pH 5.5): 818267.31
ACD/KOC (pH 5.5): 594318.50
ACD/LogD (pH 7.4): 8.08
ACD/BCF (pH 7.4): 818149.63
ACD/KOC (pH 7.4): 594233.00
Polar Surface Area: 130 Å2
Polarizability: 66.7±0.5 10-24cm3
Surface Tension: 50.9±5.0 dyne/cm
Molar Volume: 525.7±5.0 cm3

Click to predict properties on the Chemicalize site


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