Compounds > paspaline
Page last updated: 2024-11-07

paspaline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

paspaline: structure given in first source; RN given refers to (2S-(2alpha,4aalpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID115028
CHEMBL ID2408947
CHEBI ID181371
MeSH IDM0138868

Synonyms (15)

Synonym
11024-56-9
2-[(1s,2s,5s,7s,10s,11r,14s)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol
CHEBI:181371
paspaline
CHEMBL2408947
3q9sgu351d ,
unii-3q9sgu351d
2h-1-benzopyrano(5',6':6,7)indeno(1,2-b)indole-2-methanol, 3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-alpha,alpha,4a,12b,12c-pentamethyl-, (2s-(2alpha,4aalpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-
C20530
2h-1-benzopyrano(5',6':6,7)indeno(1,2-b)indole-2-methanol, 3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-.alpha.,.alpha.,4a,12b,12c-pentamethyl-, (2s,4as,4br,6as,12bs,12cs,14as)-
(-)-paspaline
(2s,4as,4br,6as,12bs,12cs,14as)-3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-.alpha.,.alpha.,4a,12b,12c-pentamethyl-2h-1-benzopyrano(5',6':6,7)indeno(1,2-b)indole-2-methanol
DTXSID70911553
2-(4a,12b,12c-trimethyl-3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-2h-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-2-yl)propan-2-ol
AKOS040753435
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organooxygen compoundAn organochalcogen compound containing at least one carbon-oxygen bond.
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
[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]

Pathways (3)

PathwayProteinsCompounds
paxilline and diprenylpaxilline biosynthesis314
paspaline biosynthesis417
lolitrem B biosynthesis520

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1594683Cytotoxicity against HEK293 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Indole Diterpenoids from an Endophytic Penicillium sp.
AID1594680Cytotoxicity against mouse L5178Y cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Indole Diterpenoids from an Endophytic Penicillium sp.
AID1122207Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay2013MedChemComm, Oct, Volume: 4, Issue:10
Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors.
AID1122208Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay2013MedChemComm, Oct, Volume: 4, Issue:10
Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors.
AID1122202Toxicity in L1 stage Caenorhabditis elegans N2 assessed as viability and reproduction at 50 uM2013MedChemComm, Oct, Volume: 4, Issue:10
Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors.
AID1594684Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human A2780 cells2019Journal of natural products, 06-28, Volume: 82, Issue:6
Indole Diterpenoids from an Endophytic Penicillium sp.
AID1122206Antimigratory activity in human MDA-MB-231 cells after 24 hrs by wound healing assay2013MedChemComm, Oct, Volume: 4, Issue:10
Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors.
AID1122203Toxicity in L1 stage Caenorhabditis elegans N2 assessed as viability and reproduction at 10 uM2013MedChemComm, Oct, Volume: 4, Issue:10
Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors.
AID1055848Inhibition of wild type L4 larval stage of Caenorhabditis elegans N2 bristol BK channel assessed as induction of reversal locomotion at 1 uM after 42 hrs2013European journal of medicinal chemistry, , Volume: 70Indole diterpene alkaloids as novel inhibitors of the Wnt/β-catenin pathway in breast cancer cells.
AID762954Antiviral activity against Influenza A virus (A/Puerto Rico/8/34(H1N1)) PR/8 infected in MDCK cells assessed as protection against virus-induced cytopathogenicity after 48 hrs by crystal-violet staining-based assay2013Journal of natural products, Jul-26, Volume: 76, Issue:7
Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492.
AID1594682Cytotoxicity against human J82 cells assessed as reduction in cell viability incubated for 72 hrs by high content analysis based fluorescent live/dead assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Indole Diterpenoids from an Endophytic Penicillium sp.
AID1055840Inhibition of Wnt/beta-catenin signaling pathway in human MDA-MB-231 cells assessed as decrease in expression of beta-catenin level at 7.6 uM after 48 hrs by DAPI staining-based confocal laser scanning microscopy2013European journal of medicinal chemistry, , Volume: 70Indole diterpene alkaloids as novel inhibitors of the Wnt/β-catenin pathway in breast cancer cells.
AID1594681Cytotoxicity against human A2780 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Indole Diterpenoids from an Endophytic Penicillium sp.
[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-19901 (7.14)18.7374
1990's0 (0.00)18.2507
2000's3 (21.43)29.6817
2010's9 (64.29)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.70

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 Index22.70 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.83 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
lysergic acid diethylamide
Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.		2.1110ergoline alkaloid;
monocarboxylic acid amide;
organic heterotetracyclic compound		dopamine agonist;
hallucinogen;
serotonergic agonist
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		3.0610diazine;
pyrazines		Daphnia magna metabolite
ribavirin
Rebetron: Rebetron is tradename		2.08101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
paxilline
paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.		4.2250diterpene alkaloid;
enone;
organic heterohexacyclic compound;
terpenoid indole alkaloid;
tertiary alcohol		anticonvulsant;
Aspergillus metabolite;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor;
genotoxin;
geroprotector;
mycotoxin;
Penicillium metabolite;
potassium channel blocker
tryptoquivaline
tryptoquivaline: tremor-producing metabolite from Aspergillus clavatus; tetrapeptide derived from tryptophan, anthranilic acid, valine, & methylalanine; structure & N1 names previously assigned to tryptoquivaline C & tryptoquivaline D found to be incorrect & are revised in third source; see also record for tryptoquivalone; structure in third source		3.0610
territrem b
territrem B: tremorgenic mycotoxin from Aspergillus terreus; RN given refers to (4aR-(4aalpha,6abeta,12aalpha,12bbeta))-isomer		3.0610
territrem a
territrem A: tremorgenic mycotoxin from Aspergillus terreus		3.0610
verruculotoxin
verruculotoxin: toxic metabolite of Penicillium verruculosum Peyronel; structure		3.0610organic heterobicyclic compound;
organonitrogen heterocyclic compound
lysergamide
lysergamide : An ergoline alkaloid comprising ergoline lacking hydrogens at positions 9 and 10 and also having a methyl group attached to the piperidine nitrogen.		2.1110ergoline alkaloid
ergonovine
Ergonovine: An ergot alkaloid (ERGOT ALKALOIDS) with uterine and VASCULAR SMOOTH MUSCLE contractile properties.. ergometrine : A monocarboxylic acid amide that is lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced.		2.1110ergot alkaloid;
monocarboxylic acid amide;
organic heterotetracyclic compound;
primary alcohol;
secondary amino compound;
tertiary amino compound		diagnostic agent;
fungal metabolite;
oxytocic;
toxin
chanoclavine
chanoclavine: RN given refers to (4R-(4alpha,5beta(E)))-isomer; structure. chanoclavine-I : An organic tricyclic compound that is 1,3,4,5-tetrahydrobenzo[cd]indole which is substituted at position 4 by a methylamino group and at position 5 by a 3-hydroxy-2-methylprop-1-en-1-yl group (the 4R,5R,E diastereoisomer). It is a precursor of the tetracyclic ergolines agroclavine, elymoclavine and lysergic acid amide.		2.1110benzoindole;
ergot alkaloid;
organic heterotricyclic compound;
primary alcohol;
secondary amino compound
verrucosidin
verrucosidin: tremorgenic mycotoxin; structure given in first source; RN given refers to (1alpha,2alpha(1E(2S*,3R*),3E),4alpha,5alpha)-(+-)-isomer		3.0610
ergoline
Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.		2.1110diamine;
ergoline alkaloid;
indole alkaloid fundamental parent;
indole alkaloid;
organic heterotetracyclic compound
emindole SB
[no description available]		3.0240terpenoid indole alkaloidAspergillus metabolite;
marine metabolite;
Penicillium metabolite
lolitrem b
lolitrem B: neurotoxin from staggers-producing ryegrass pastures; MF C42-H55-N-O7		3.0610
verruculogen
verruculogen: complex 6-O-methylindole cpd containing 3 nitrogens; induces tremor; tremorigenic metabolite from Penicillium verruculosum isolated from moldy peanuts; decreases GABA levels in CNS; structure. verruculogen : An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species.		3.0610aromatic ether;
diol;
indole alkaloid;
organic heterohexacyclic compound;
organic peroxide		Aspergillus metabolite;
GABA modulator;
mycotoxin;
Penicillium metabolite;
potassium channel blocker
aflatrem
aflatrem: tremorgenic toxin isolated from Aspergillus flavus; structure		3.0610organic heterotricyclic compound;
organooxygen compound
phytoestrogens
Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0810
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0810
Cancer of Ovary
[description not available]		02.2110
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.2110
Action Tremor
[description not available]		03.820
Tremor
Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.		08.820