Page last updated: 2024-11-10

phorbol 12-phenylacetate 13-acetate 20-homovanillate

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Description

phorbol 12-phenylacetate 13-acetate 20-homovanillate: behavior contrasts with resiniferatoxin and capsaicin in the lack of cooperativity in binding vanilloid (capsaicin) receptor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035862
CHEMBL ID104647
MeSH IDM0264503

Synonyms (22)

Synonym
phenyl-acetic acid (1ar,1bs,4ar,7as,7bs,8r,9r,9as)-9a-acetoxy-4a,7b-dihydroxy-3-[2-(4-hydroxy-3-methoxy-phenyl)-acetoxymethyl]-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 ester
bdbm50052440
phorbol 12-phenylacetate 13-acetate 20-homovanillate, solid
NCGC00162421-01
175796-50-6
phorbol 12-phenylacetate 13-acetate 20-homovanillate
gtpl2490
ppahv
phorbol-12-phenylacetate-13-acetate-20-homovanillate
CHEMBL104647 ,
NCGC00162421-02
benzeneacetic acid, 4-hydroxy-3-methoxy-, (9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,9,9a-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9-((phenylacetyl)oxy)-1h-cyclopropa(3,4)benz(1,2-e)azulen-3-yl)methyl ester, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,
[(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-9a(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9-[phenylacetyl)oxy]-1h-cyclopropa[3,4]benz[1,2-e]azulen-3-yl]methyl ester benzeneacetic acid
AKOS024456617
J-011134
ppahv >99%
[(1s,2s,6r,10s,11r,13s,14r,15r)-13-acetyloxy-1,6-dihydroxy-8-[[2-(4-hydroxy-3-methoxyphenyl)acetyl]oxymethyl]-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] 2-phenylacetate
{9a-(acetyloxy)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9-[(phenylacetyl)oxy]-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1h-cyclopropa[3,4]benzo[1,2-e]azulen-3-yl}methyl (4-hydroxy-3-methoxyphenyl)acetate
DTXSID10938709
Q27088432
benzeneacetic acid, 4-hydroxy-3-methoxy-, [(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9-[(phenylacetyl)oxy]-1h-cyclopropa[3,4]benz[1,2-e]azulen-3-yl]methyl ester
12-o-phenylacetyl-13-o-acetylphorbol-20-homovanillate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, CruzipainTrypanosoma cruziPotency10.00000.002014.677939.8107AID1476
Microtubule-associated protein tauHomo sapiens (human)Potency25.51540.180013.557439.8107AID1460; AID1468
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency15.84890.035520.977089.1251AID504332
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency7.07950.016525.307841.3999AID602332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily V member 1Rattus norvegicus (Norway rat)Ki2.62500.00010.64456.4000AID184409; AID187143; AID218305; AID218306
Transient receptor potential cation channel subfamily V member 1Homo sapiens (human)Ki2.83340.00010.67956.4000AID159554; AID218305; AID218306
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IITransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
fever generationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
microglial cell activationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
diet induced thermogenesisTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
peptide secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of systemic arterial blood pressureTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
lipid metabolic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cell surface receptor signaling pathwayTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chemosensory behaviorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of heart rateTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of mitochondrial membrane potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
glutamate secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to heatTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of apoptotic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to peptide hormoneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
behavioral response to painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
sensory perception of mechanical stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein homotetramerizationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory postsynaptic potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
smooth muscle contraction involved in micturitionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to alkaloidTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to ATPTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to tumor necrosis factorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to acidic pHTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to temperature stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of establishment of blood-brain barrierTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion import across plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to capsazepineTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to nerve growth factor stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
transmembrane signaling receptor activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
voltage-gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calmodulin bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
ATP bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
intracellularly gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chloride channel regulator activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphatidylinositol bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
metal ion bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphoprotein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
temperature-gated ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
external side of plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
dendritic spine membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
neuronal cell bodyTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
postsynaptic membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1346643Rat TRPV1 (Transient Receptor Potential channels)2001British journal of pharmacology, Mar, Volume: 132, Issue:5
Pharmacological differences between the human and rat vanilloid receptor 1 (VR1).
AID1231846Antiviral activity against chikungunya virus Indian ocean strain 899 infected in Vero cells assessed as virus-induced cytopathic effect after 6 to 7 days2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID159554Inhibitory constant for RTX binding to porcine spinal cord1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID1231847Selectivity index, CC50 for african green monkey Vero cells to EC50 for chikungunya virus Indian ocean strain 8992015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID1231849Selectivity index, CC50 for african green monkey Vero cells to EC50 for HIV1 3B2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID226640Effect on cooperativity of Resiniferatoxin (RTX) binding (Hill coefficient)1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID1231851Selectivity index, CC50 for african green monkey Vero cells to EC50 for HIV2 ROD2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID1231850Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID1231848Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication.
AID187143Inhibition of [3H]- RTX binding to vanilloid receptor of rat urinary bladder1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID218308Displacement of [3H]RTX binding from Vanilloid receptor of rat dorsal Root Ganglion (DRG) membranes1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID218306Inhibition of [3H]- RTX binding to Vanilloid receptors from pig spinal cord1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID89933Inhibitory constant for RTX binding to human spinal cord1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID184409Inhibitory constant for RTX binding to rat spinal cord1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID177830Desensitisation against RTX-induced ear edema formation 24 hr r post-administration1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
AID218305Inhibition of [3H]- RTX binding to Vanilloid receptors from human spinal cord1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Synthesis and evaluation of phorboid 20-homovanillates: discovery of a class of ligands binding to the vanilloid (capsaicin) receptor with different degrees of cooperativity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (21.43)18.2507
2000's10 (71.43)29.6817
2010's1 (7.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.59

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.59 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]