Compounds > seneciphylline
Page last updated: 2024-12-10

seneciphylline

Description

seneciphylline: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5281750
CHEMBL ID523911
CHEBI ID9108
CHEBI ID92677
SCHEMBL ID177867
MeSH IDM0061625

Synonyms (62)

Synonym
BRD-K38449220-001-03-8
PRESTWICK2_000599
nsc-30622
pyrrolizine-2, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino[2,3,4-gh]-
mls000737616 ,
senecionan-11, 13,19-didehydro-12-hydroxy-
seneciphyllin
NSC30622 ,
nsc 30622
nci-c61165
seniciphylline
ccris 4336
senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-
trans-15-ethylidene-12beta-hydroxy-12alpha-methyl-13-methylenesenec-1-enine
hsdb 5188
BSPBIO_000478
PRESTWICK_446
PRESTWICK3_000599
BPBIO1_000526
(z)-ethylidene-hydroxy-methyl-methylene-[?]dione
13,19-didehydro-12-hydroxysenecionan-11,16-dione
jacodine
480-81-9
seneciphylline
smr000393787
(3z,6r,14ar,14br)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
NCGC00142562-03
MLS002222214
CHEMBL523911
chebi:9108 ,
HMS1569H20
NCGC00017384-04
HMS2096H20
(1r,7r,17r)-4-ethylidene-7-hydroxy-7-methyl-6-methylene-2,9-dioxa-14-azatricyc lo[9.5.1.0<14,17>]heptadec-11-ene-3,8-dione
HMS2763J21
(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3z,6r,14ar,14br)-
unii-0zyz9l5454
0zyz9l5454 ,
seneciphynine
(3z,6r,14ar,14br)-3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione
alpha-longilobine
seneciphylline [mi]
seneciphylline [hsdb]
.alpha.-longilobine
seneciphylline [iarc]
SCHEMBL177867
AKOS024282719
AC-34599
2h-pyran-2-carboxylicacid,5-ethyltetrahydro-2,3-dimethyl-6-oxo-(9ci)
DTXSID8026016
mfcd00221722
seneciphylline, analytical standard
CHEBI:92677
bdbm50480273
HY-N1282
(6r,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
(1r,4z,7r,17r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Q27108272
[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3z,6r,14ar,14br)-
CS-0016686
MS-25026
seneciphylline 100 microg/ml in water

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with seneciphylline and senkirkine had adverse effects on the development and organic morphodifferentiation of embryos."( [Embryotoxicity of Senecionis Scandentis Hebra on in vitro cultured mouse embryos].
Cui, HY; Han, JY; Li, CY; Liang, AH; Lu, YT; Yi, Y; Zhang, YS; Zhao, Y, 2014)		0.74

Toxicity

ExcerptReferenceRelevance
" In this study the content of the alkaloids senecionine (SCO), senkirkin (SKK) and seneciphyllin (SCP) and their toxic effects in cattle were studied."( Interplant alkaloid variation and Senecio vernalis toxicity in cattle.
Brimer, L; Friis, C; Skaanild, MT, 2001)		0.31
"Pyrrolizidine alkaloids (PAs) are feeding deterrents and toxic compounds to generalist herbivores."( Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.
Klinkhamer, PG; Leiss, KA; Nuringtyas, TR; van Oers, MM; Verpoorte, R, 2014)		0.4
" Treatment with seneciphylline and senkirkine had adverse effects on the development and organic morphodifferentiation of embryos."( [Embryotoxicity of Senecionis Scandentis Hebra on in vitro cultured mouse embryos].
Cui, HY; Han, JY; Li, CY; Liang, AH; Lu, YT; Yi, Y; Zhang, YS; Zhao, Y, 2014)		0.75

Dosage Studied

ExcerptRelevanceReference
" Lactating rats dosed with these differently labelled pyrrolizidine alkaloids (PAs) excreted within 3 h approx."( Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues.
Heim, T; Lüthy, J; Schlatter, C, 1983)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrrolizine alkaloid
[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 Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
TDP1 proteinHomo sapiens (human)Potency21.85280.000811.382244.6684AID686978; AID686979
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency112.20200.354828.065989.1251AID504847
Guanine nucleotide-binding protein GHomo sapiens (human)Potency25.11891.995325.532750.1187AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID397122Inhibition of HIV1 RT
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (28.13)18.7374
1990's6 (18.75)18.2507
2000's3 (9.38)29.6817
2010's11 (34.38)24.3611
2020's3 (9.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.23

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.23 (24.57)
Research Supply Index3.58 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.23)

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%
Other35 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
n,n-dimethylaniline
N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.		1.9710dimethylaniline;
tertiary amine
iproniazid
[no description available]		1.9710carbohydrazide;
pyridines
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		1.9810pyrrole;
secondary amine
thiazoles
[no description available]		2.11101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
monocrotaline
Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.		7.730pyrrolizidine alkaloid
retronecine
retronecine: RN given refers to (1R-trans)-isomer; structure		7.3720pyrrolizines
thiazolyl blue
thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.		2.1110organic bromide saltcolorimetric reagent;
dye
1-phenylimidazole
1-phenylimidazole: ligand for cytochrome P-450 & inhibitor of microsomal oxidation		1.9710
jacobine
jacobine: RN given refers to (15alpha,20S)-isomer; structure		2.5220pyrrolizine alkaloid
heliotrine
[no description available]		2.1110pyrrolizines
trichodesmine
[no description available]		6.9810
senecionine
senecionine: RN given refers to parent cpd; structure. senecionine : A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.		3.94130lactone;
pyrrolizidine alkaloid;
tertiary alcohol		plant metabolite
retrorsine
retrorsine: RN given refers to cpd without isomeric designation; structure		7.9340macrolide
riddelliine
riddelliine: structure. riddelliine : A macrodiolide that is 13,19-didehydrosenecionan bearing two additional hydroxy substituents at positions 12 and 18 as well as two additional oxo groups at positions 11 and 16.		2.1110macrodiolide;
olefinic compound;
organic heterotricyclic compound;
pyrrolizine alkaloid		carcinogenic agent;
genotoxin;
mutagen
senkirkine
senkirkine: macrocyclic secopyrrolizidine alkaloid from Senecio; structure given in first source; RN given refers to senkirkine		8.150macrolide
senecionine n-oxide
senecionine N-oxide: isolated from Senecio vulgaris L.; structure given in first source		2.1510tertiary amine oxide
lasiocarpine
lasiocarpine: RN given refers to parent cpd(1S-(1alpha(Z),7(2S*,3R*),7aalpha))-isomer; structure		2.1110pyrrolizines
riddelliine n-oxide
riddelliine N-oxide: structure given in first source; from Riddell groundsel (Senecio riddellii). riddelliine N-oxide : A pyrrolizine alkaloid that is 13,19-didehydrosenecionane bearing two additional hydroxy substituents at positions 12 and 18, two additional oxo groups at positions 11 and 16 and an N-oxido substituent.		2.1110diol;
macrocyclic lactone;
olefinic compound;
organic heterotricyclic compound;
primary alcohol;
pyrrolizine alkaloid;
tertiary alcohol;
tertiary amine oxide		carcinogenic agent;
genotoxin;
human xenobiotic metabolite;
Jacobaea metabolite;
mutagen;
rat metabolite
necic acid
necic acid: occur as diesters of pyrrolizidine bases in alkaloids; RN given refers to (Z)-isomer; structure		1.9610
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.2510
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
Acute Liver Injury, Drug-Induced
[description not available]		02.2510
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.2510
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.3110
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.420
Diathesis
[description not available]		01.9310
Bovine Diseases
[description not available]		0210
Plant Poisoning
Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.		0210
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