Page last updated: 2024-11-08

phorbol

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Description

phorbol: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9b beta))-isomer; synonym isophorbol refers to (4a alpha)-isomer; structure in Merck Index, 9th ed, #7143 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phorbol : A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions. [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]

Cross-References

ID SourceID
PubMed CID442070
CHEMBL ID124518
CHEBI ID8116
SCHEMBL ID14937
MeSH IDM0102830

Synonyms (53)

Synonym
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9a alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-, (+)-
1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
hsdb 4328
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,6,8-tetramethyl-, (1ar-(1aalpha,1beta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
4-beta-phorbol
nsc 154778
ccris 694
CHEBI:8116 ,
(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5h-cyclopropa[3,4]benzo[1,2-e]azulen-5-one
4,9,12beta,13,20-pentahydroxytiglia-1,6-dien-3-one
4,9,12beta,13,20-pentahydroxy-1,6-tigliadien-3-on
SMP2_000151
4,9,12-beta,13,20-pentahydroxy-1,6-tigliadien-3-on
4-.beta.-phorbol
4.b.-phorbol
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alpha-tetramethyl-
C09155
17673-25-5
phorbol
nsc-154778
LMPR0104330001
CHEMBL124518
xuz76s9127 ,
unii-xuz76s9127
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1ar,1bs,4ar,7as,7bs,8r,9r,9as)-
5h-cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-
4beta,9alpha,12beta,13alpha,20-pentahydroxytiglia-1,6-dien-3-one
SCHEMBL14937
phorbol [hsdb]
(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one
phorbol [mi]
QGVLYPPODPLXMB-UBTYZVCOSA-N
AKOS024418764
AC-33956
DTXSID2021155
SR-05000002211-2
sr-05000002211
HY-N2147
CS-6052
J-011221
mfcd00065450
(1ar,1bs,4ar,7as,7bs,8r,9r,9as)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1b,4,4a,7a,7b,8,9,9a-octahydro-1h-cyclopropa[3,4]benzo[1,2-e]azulen-5(1ah)-one
BS-16283
Q2705359
(+)-phorbol
4b-phorbol
5-[2-(diethylamino)ethyl]-3-phenyl-1,2,4-oxadiazolecitratesalt
EX-A3092
CCG-268216
A881502
S9389
(1s,2s,6r,10s,11r,13s,14r,15r)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
P2732

Research Excerpts

Effects

ExcerptReferenceRelevance
"Phorbol, which has a molecular structure similar to TPA but does not have any tumor-promoting activity, showed no such stimulatory effect on SV40 induction."( Tumor promoter 12-O-tetradecanoylphorbol 13-acetate stimulates simian virus 40 induction by DNA-damaging agents and tumor initiators.
Nomura, S; Oishi, M; Shobu, N, 1983
)
1.27
"Phorbol, which has a molecular structure similar to TPA but does not have any tumor-promoting activity, showed no such stimulatory effect on SV40 induction."( Tumor promoter 12-O-tetradecanoylphorbol 13-acetate stimulates simian virus 40 induction by DNA-damaging agents and tumor initiators.
Nomura, S; Oishi, M; Shobu, N, 1983
)
1.27

Actions

ExcerptReferenceRelevance
"1. Phorbol esters activate protein kinase C (PKC) and also increase the secretion of neurotransmitter substances by an unknown mechanism. "( Opposing effects of phorbol esters on transmitter release and calcium currents at frog motor nerve endings.
Hirsh, JK; Redman, RS; Searl, TJ; Silinsky, EM, 1997
)
1.24

Treatment

Phorbol ester treatment of leukocytes in vitro significantly increased expression on MO and PMN, but not LY. Treatment with phorbol-12-myristate-13-acetate (PMA) resulted in a dose-dependent increase in the secretion of CT and CgA.

ExcerptReferenceRelevance
"Phorbol ester treatment of leukocytes in vitro significantly increased expression on MO and PMN, but not LY."( The leukointegrin alpha d/beta 2 (alpha d/CD18): specific changes in surface expression in patients on hemodialysis.
Agosti, SJ; Gallatin, WM; Hakala, S; Hoffman, P; Rabb, H; Ramirez, G, 1998
)
1.02
"Treatment with phorbol-12-myristate-13-acetate (PMA) resulted in a dose-dependent increase in the secretion of both CT and CgA by the two cell lines."( The coregulation of secretion and cytoplasmic ribonucleic acid of chromogranin-A and calcitonin by phorbol ester in cells that produce both substances.
Burton, DW; Deftos, LJ; Murray, SS, 1988
)
0.83
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (5)

ClassDescription
tetracyclic diterpenoidA diterpenoid with a tetracyclic skeleton.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
cyclic ketone
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups.
[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]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1630708Cytotoxicity against human HuH7 cells after 72 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Antitubercular and cytotoxic tigliane-type diterpenoids from Croton tiglium.
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.
AID718287Selectivity index, ratio of CC50 for african green monkey Vero cells to EC50 for Chikungunya virus 8992012Journal of natural products, Dec-28, Volume: 75, Issue:12
Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication.
AID718288Antiviral activity against Sindbis virus HRsp infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect incubated for 6 to 7 days by MTS assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication.
AID1808885Induction of TGFalpha release in serum-starved HEK293T cells coexpressing GFP fused mCherry assessed as reduction in mCherry/GFP ratio at 0.5 uM measured up to 180 mins by time-lapse microscopic analysis2021Journal of medicinal chemistry, 05-13, Volume: 64, Issue:9
Phorbol Diesters and 12-Deoxy-16-hydroxyphorbol 13,16-Diesters Induce TGFα Release and Adult Mouse Neurogenesis.
AID718290Cytotoxicity against african green monkey Vero cells by MTS assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication.
AID1630707Cytotoxicity against human A549 cells after 72 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Antitubercular and cytotoxic tigliane-type diterpenoids from Croton tiglium.
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.
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.
AID144651Inhibition of cell growth in NCI panel of 60 human carcinoma lines2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Iridals are a novel class of ligands for phorbol ester receptors with modest selectivity for the RasGRP receptor subfamily.
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.
AID718289Antiviral activity against Chikungunya virus 899 infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect incubated for 6 to 7 days by MTS assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication.
AID718286Antiviral activity against Semliki forest virus infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect incubated for 6 to 7 days by MTS assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus 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.
AID1630709Antitubercular activity against Mycobacterium tuberculosis H37Ra incubated for 7 days by Alamar blue dye-based fluorometric assay2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Antitubercular and cytotoxic tigliane-type diterpenoids from Croton tiglium.
AID1630706Cytotoxicity against human K562 cells after 72 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Antitubercular and cytotoxic tigliane-type diterpenoids from Croton tiglium.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (132)

TimeframeStudies, This Drug (%)All Drugs %
pre-199047 (35.61)18.7374
1990's36 (27.27)18.2507
2000's26 (19.70)29.6817
2010's17 (12.88)24.3611
2020's6 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 57.75

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index57.75 (24.57)
Research Supply Index4.91 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index94.18 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (57.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.74%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other134 (99.26%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]