Compounds > sapintoxin a
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sapintoxin a

Description

sapintoxin A: from unripe fruits of Sapium indicum; rapidly acting proinflammatory agent on mammalian skin, but considerably less potent than tetradecanoylphorbol acetate; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID108085
CHEMBL ID503534
MeSH IDM0100186

Synonyms (14)

Synonym
79083-69-5
sapintoxin a
benzoic acid, 2-(methylamino)-, (1ar,1bs,4as,7ar,7br,8r,9r,9as)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-7b-hydroxy-3-(hydroxymentyl)-1,1,6,6-tetramethyl-5-oxo-1h-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester
benzoic acid, 2-(methylamino)-, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1h-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1ar-(1a-alpha,1b-beta,4a-beta,7a-alpha,7b-alpha,8-alpha,9-beta,9a-al
CHEMBL503534
12-o-(n-methylaminobenzoyl)-13-o-acetyl-4-deoxyphorbol
(1ar,1bs,4as,7ar,7br,8r,9r,9as)-9a-acetoxy-7b-hydroxy-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 2-(methylamino)benzoate
DTXSID601000255
9a-(acetyloxy)-7b-hydroxy-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 2-(methylamino)benzoate
[(1r,2r,6s,10s,11r,13s,14r,15r)-13-acetyloxy-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] 2-(methylamino)benzoate
benzoic acid, 2-(methylamino)-, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1h-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, [1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha)]-
(1r,2r,6s,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate
benzoic acid, 2-(methylamino)-, (1ar,1bs,4as,7ar,7br,8r,9r,9as)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1h-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester
2HF34UL2QC

Effects

ExcerptReference
"Sapintoxin A has properties in common with promoters such as 12-o-tetradecanoylphorbol 13-acetate (TPA) in that it will induce erythema in vivo, induce lymphocyte mitogenesis in vitro and cause aggregation of human and rabbit platelets."( Aitken, A; Brooks, G; Evans, AT; Evans, FJ, 1987)

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1875663Therapeutic index, ratio of cytotoxicity against human MT4 cells to antiviral activity against HIV NL4-32022Journal of natural products, 11-25, Volume: 85, Issue:11
Tigliane-Type Diterpene Esters from the Fruits of
AID1875662Antiviral activity against HIV NL4-3 infected in MT-4 cells assessed as viral replication measured after 4 days by p24-ELISA2022Journal of natural products, 11-25, Volume: 85, Issue:11
Tigliane-Type Diterpene Esters from the Fruits of
AID355724Antimycobacterial activity against Mycobacterium tuberculosis H37Ra2003Journal of natural products, Apr, Volume: 66, Issue:4
Antimycobacterial activity of phorbol esters from the fruits of Sapium indicum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's4 (50.00)18.2507
2000's1 (12.50)29.6817
2010's0 (0.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
isoniazid[no description available]medium10carbohydrazideantitubercular agent;
drug allergen
kanamycin sulfate[no description available]medium10aminoglycoside sulfate saltantibacterial drug;
geroprotector
zidovudine[no description available]medium10azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
sapintoxin d[no description available]medium20phorbol ester;
tertiary alpha-hydroxy ketone		fluorescent probe;
metabolite
phorbols[no description available]medium10diterpene;
terpenoid fundamental parent
12-deoxyphorbolphenylacetate[no description available]medium30
tetradecanoylphorbol acetate[no description available]medium30acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
arachidonic acid[no description available]medium10icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
sq-23377[no description available]medium10cyclic ether;
enol;
polyunsaturated fatty acid;
very long-chain fatty acid		calcium ionophore;
metabolite
manganese[no description available]medium10elemental manganese;
manganese group element atom		Escherichia coli metabolite;
micronutrient
resiniferatoxin[no description available]medium20carboxylic ester;
diterpenoid;
enone;
monomethoxybenzene;
organic heteropentacyclic compound;
ortho ester;
phenols;
tertiary alpha-hydroxy ketone		analgesic;
neurotoxin;
plant metabolite;
TRPV1 agonist
1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1h-imidazole[no description available]medium10ether;
imidazoles;
monomethoxybenzene		TRP channel blocker
n-formylmethionine leucyl-phenylalanine[no description available]medium10tripeptide
epidermal growth factor[no description available]medium10
phorbol 12,13-dibutyrate[no description available]medium10butyrate ester;
phorbol ester;
tertiary alpha-hydroxy ketone
ConditionIndicatedRelationship StrengthStudiesTrials
Erythema0low10
Experimental Neoplasms0low10
HIV0low30
Neoplasms, Experimental0low10

Research Highlights

Dosage (1)

ArticleYear
Both tumour-promoting and non-promoting phorbol esters inhibit [125I]EGF binding and stimulate the phosphorylation of an 80 kd protein kinase C substrate protein in intact quiescent swiss 3T3 cells.
Carcinogenesis, Volume: 11, Issue: 4		1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]