4alpha-phorbol 12,13-didecanoate : 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 decanoate esters. A Trpv4-specific ligand. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 452544 |
| CHEMBL ID | 118987 |
| CHEBI ID | 139299 |
| MeSH ID | M0310504 |
| Synonym |
|---|
| 4-alpha-phorbol-12,13-didecanoate |
| 4-.alpha.-phorbol didecanoate |
| 27536-56-7 |
| 4-.alpha.-phorbol 12,13-didecanoate |
| [decanoyloxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] decanoate |
| decanoic acid, (1ar,1bs,4as,7as,7bs,8r,9r,9as)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa[3,4]benz[1,2-e]azulene-9,9a-diyl ester |
| 4alpha-phorbol 12,13-didecanoate, solid |
| 4alphapdd |
| 4alpha-phorbol-12,13-didecanoate |
| 4alpha-phorbol-didecanoate |
| 4alpha-pdd |
| 4alpha-phorbol 12,13-didecanoate |
| gtpl2500 |
| CHEBI:139299 |
| 12,13-didecanoyl-4alpha-phorbol |
| bdbm50240777 |
| decanoic acid (1ar,1bs,4as,7as,7bs,8r,9r,9as)-9-decanoyloxy-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester |
| CHEMBL118987 , |
| 4-alpha-phorbol 12,13-didecanoate |
| decanoic acid, 1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester, (1ar-(1aalpha,1bbeta,4aalpha,7aalpha,7balpha,8alpha,9beta,9aalpha))- |
| 4alpha-phorbol 12,13-dideconate |
| 4|a-phorbol 12,13-didecanoate |
| J-016805 |
| 4alpha-phorbol-12,13-didecanoate - cas 27536-56-7 |
| Q27073750 |
| decanoicacid,1,1'-[(1ar,1bs,4as,7as,7bs,8r,9r,9as)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa[3,4]benz[1,2-e]azulene-9,9a-diyl]ester |
| 4 alpha -phorbol 12,13-didecanoate |
| [(1s,2s,6s,10s,11r,13s,14r,15r)-13-decanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate |
| 4-phorbol 12,13-didecanoate |
| HY-116291 |
| 4+/--phorbol 12,13-didecanoate |
| CBA53656 |
| PD040428 |
| DTXSID901098483 |
| 1,1'-[(1ar,1bs,4as,7as,7bs,8r,9r,9as)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa[3,4]benz[1,2-e]azulene-9,9a-diyl] didecanoate |
| AKOS040747628 |
| Role | Description |
|---|---|
| TRPV4 agonist | An agonist at the transient receptor potential vanilloid 4 (TRPV4). |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| phorbol ester | Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C. |
| decanoate ester | A fatty acid ester resulting from the formal condensation of the carboxy group of decanoic acid (capric acid) with the hydroxy group of an alcohol or phenol. |
| tertiary alpha-hydroxy ketone | An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups. |
| diester | A diester is a compound containing two ester groups. |
| primary allylic alcohol | An allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to two hydrogens. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Transient receptor potential cation channel subfamily V member 4 | Mus musculus (house mouse) | EC50 (µMol) | 2.6720 | 0.1500 | 1.3800 | 6.3000 | AID1667132; AID353524; AID353781; AID353782; AID353783 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1346605 | Human TRPV4 (Transient Receptor Potential channels) | 2003 | British journal of pharmacology, Sep, Volume: 140, Issue:2 | Protein kinase C-mediated Ca2+ entry in HEK 293 cells transiently expressing human TRPV4. |
| AID1346607 | Mouse TRPV4 (Transient Receptor Potential channels) | 2002 | The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16 | Activation of TRPV4 channels (hVRL-2/mTRP12) by phorbol derivatives. |
| AID353524 | Activation of mouse wild type TRPV4 expressed in HEK293 cells assessed as increase in intracellular calcium concentration | 2009 | Journal of medicinal chemistry, May-14, Volume: 52, Issue:9 | Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. |
| AID1231847 | Selectivity index, CC50 for african green monkey Vero cells to EC50 for chikungunya virus Indian ocean strain 899 | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID1231848 | Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID1667132 | Agonist activity at mouse TRPV4 | 2020 | Bioorganic & medicinal chemistry letters, 04-15, Volume: 30, Issue:8 | Recent advances in TRPV4 agonists and antagonists. |
| AID1231850 | Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID1231851 | Selectivity index, CC50 for african green monkey Vero cells to EC50 for HIV2 ROD | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID353781 | Activation of mouse TRPV4 Y556A mutant expressed in HEK293 cells assessed as increase in intracellular calcium concentration | 2009 | Journal of medicinal chemistry, May-14, Volume: 52, Issue:9 | Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. |
| AID353785 | Effect on intracellular calcium level in non transfected HEK293 cells assessed as increase in fura-2 ratio | 2009 | Journal of medicinal chemistry, May-14, Volume: 52, Issue:9 | Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. |
| AID353783 | Activation of mouse TRPV4 W586A mutant expressed in HEK293 cells assessed as increase in intracellular calcium concentration | 2009 | Journal of medicinal chemistry, May-14, Volume: 52, Issue:9 | Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. |
| AID1231846 | Antiviral activity against chikungunya virus Indian ocean strain 899 infected in Vero cells assessed as virus-induced cytopathic effect after 6 to 7 days | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID1231849 | Selectivity index, CC50 for african green monkey Vero cells to EC50 for HIV1 3B | 2015 | Journal of natural products, Jun-26, Volume: 78, Issue:6 | Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication. |
| AID353782 | Activation of mouse TRPV4 S557A mutant expressed in HEK293 cells assessed as increase in intracellular calcium concentration | 2009 | Journal of medicinal chemistry, May-14, Volume: 52, Issue:9 | Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 3 (60.00) | 29.6817 |
| 2010's | 1 (20.00) | 24.3611 |
| 2020's | 1 (20.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.63) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (20.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 4 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||