Page last updated: 2024-11-05

lysergol

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

Description

lysergol: structure given in first source; RN given refers to (8beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lysergol : An alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi and in the morning glory family of plants. Its structure is that of ergoline with a methyl group at N-6 and a beta-hydroxymethyl substituent at C-8. [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 CID14987
CHEMBL ID39947
CHEBI ID60528
SCHEMBL ID178071
MeSH IDM0171493

Synonyms (56)

Synonym
ntr684z1az ,
1413-67-8
(7-methyl-4,6,6a,7,8,9-hexahydro-indolo(4,3-fg)quinolin-9-yl)-methanol
unii-ntr684z1az
BRD-K27871032-001-02-6
BRD-K27871032-001-04-2
gtpl123
[(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol
lysergol
DIVK1C_000515
KBIO1_000515
MLS001049075
smr000386913
(7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol
MEGXP0_001732
PRESTWICK_308
phytochem 12: 2435 (1973)
NCGC00017367-01
tnp00316
BSPBIO_000528
PRESTWICK3_000454
ACON0_000797
PRESTWICK2_000454
BPBIO1_000582
ACON1_000057
PRESTWICK1_000454
SPBIO_002467
PRESTWICK0_000454
NINDS_000515
SMP1_000185
IDI1_000515
CHEMBL39947 ,
(6-methyl-9,10-didehydroergolin-8beta-yl)methanol
CHEBI:60528 ,
HMS501J17
HMS1569K10
bdbm50016479
cid_14987
HMS2096K10
HMS2271M04
SCHEMBL178071
BIXJFIJYBLJTMK-MEBBXXQBSA-N
AKOS030490884
sr-01000758923
SR-01000758923-3
(8beta)-9,10-didehydro-6-methylergoline-8-methanol; ergoline-8beta-methanol, 9,10-didehydro-6-methyl- (8ci); lysergol (6ci,7ci); indolo[4,3-fg]quinoline, ergoline-8-methanol deriv.; nsc 196867
E75857
AS-18087
Q6710130
((6ar,9r)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol
HY-N6809
CS-0092658
[(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinolin-9-yl]methanol
A923435
((6ar)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol
mfcd00010029

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Little is known about the bioavailability of LA because of limitations in available analytical protocols."( Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.
Craig, AM; Fleischmann, T; Lodge-Ivey, SL; True, JE; Walker, K, 2006
)
0.33
" The results of the study inferred that lysergol improved the oral bioavailability of berberine."( Simultaneous quantification of berberine and lysergol by HPLC-UV: evidence that lysergol enhances the oral bioavailability of berberine in rats.
Anandjiwala, S; Dash, RP; Nivsarkar, M; Patil, S, 2012
)
0.91
"The current review emphasizes on the herbal bioenhancers which themselves do not possess inherent pharmacological activity of their own but when co-administered with Active Pharmaceutical Ingredients (API), enhances their bioavailability and efficacy."( Role of herbal bioactives as a potential bioavailability enhancer for Active Pharmaceutical Ingredients.
Alexander, A; Kumari, L; Qureshi, A; Saraf, S; Sharma, M; Vaishnav, P, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ergoline alkaloidOne of a class of naturally occurring alkaloids with a structure based on that of ergoline.
[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 (37)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.79430.003245.467312,589.2998AID2517
Chain A, HADH2 proteinHomo sapiens (human)Potency15.84890.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency15.84890.025120.237639.8107AID886
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency50.11870.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
thioredoxin reductaseRattus norvegicus (Norway rat)Potency18.73830.100020.879379.4328AID588453; AID588456
phosphopantetheinyl transferaseBacillus subtilisPotency1.99530.141337.9142100.0000AID1490
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID743255
TDP1 proteinHomo sapiens (human)Potency10.01130.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency25.78770.180013.557439.8107AID1460; AID1468
thioredoxin glutathione reductaseSchistosoma mansoniPotency11.22020.100022.9075100.0000AID485364
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency12.58930.011212.4002100.0000AID1030
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency0.02510.00207.533739.8107AID891
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency35.48130.036619.637650.1187AID2100
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency8.91253.548119.542744.6684AID743266
importin subunit beta-1 isoform 1Homo sapiens (human)Potency78.43525.804836.130665.1308AID540253; AID540263
flap endonuclease 1Homo sapiens (human)Potency12.58930.133725.412989.1251AID588795
ubiquitin carboxyl-terminal hydrolase 2 isoform aHomo sapiens (human)Potency3.98110.65619.452025.1189AID463254
snurportin-1Homo sapiens (human)Potency78.43525.804836.130665.1308AID540253; AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency56.23410.425612.059128.1838AID504891
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency44.66845.804816.996225.9290AID540253
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency31.62280.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency4.10950.004611.374133.4983AID624296
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency3.98110.00419.962528.1838AID2675
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
trace amine-associated receptor 1Homo sapiens (human)IC50 (µMol)4.57700.15713.82579.3940AID686984
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)IC50 (µMol)0.01500.00031.38338.4000AID3674
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)IC50 (µMol)0.01500.00051.48357.8000AID3674
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)IC50 (µMol)0.01500.00311.73607.8000AID3674
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)IC50 (µMol)0.01500.00501.79627.8000AID3674
BZLF2Human herpesvirus 4 type 2 (Epstein-Barr virus type 2)IC50 (µMol)12.38000.42004.434216.2300AID1419
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
mu-type opioid receptor isoform MOR-1Homo sapiens (human)EC50 (µMol)92.47000.13203.30049.5690AID624499
POsterior SegregationCaenorhabditis elegansEC50 (µMol)20.60502.201047.1808186.6810AID1964
trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)7.62700.06852.11849.9700AID686985
kallikrein-7 isoform 1 preproproteinHomo sapiens (human)EC50 (µMol)7.72302.57507.18789.4550AID720500
5-hydroxytryptamine receptor 2AMus musculus (house mouse)EC50 (µMol)0.01800.00381.36218.3930AID624503
Sodium-dependent noradrenaline transporter Homo sapiens (human)EC50 (µMol)53.18600.082031.0243168.9080AID1960
Zinc finger protein mex-5Caenorhabditis elegansEC50 (µMol)53.18600.082033.5679168.9080AID1960
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent noradrenaline transporter Homo sapiens (human)
chemical synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent noradrenaline transporter Homo sapiens (human)
response to painSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent noradrenaline transporter Homo sapiens (human)
neuron cellular homeostasisSodium-dependent noradrenaline transporter Homo sapiens (human)
amino acid transportSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
actin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
protein bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
alpha-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
metal ion bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
beta-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
cell surfaceSodium-dependent noradrenaline transporter Homo sapiens (human)
membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
presynaptic membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
axonSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346264Human 5-HT1B receptor (5-Hydroxytryptamine receptors)1992Proceedings of the National Academy of Sciences of the United States of America, Apr-15, Volume: 89, Issue:8
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
AID624230Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e1996Journal of neurochemistry, Nov, Volume: 67, Issue:5
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
AID1346264Human 5-HT1B receptor (5-Hydroxytryptamine receptors)1996Journal of neurochemistry, Nov, Volume: 67, Issue:5
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
AID1346528Human 5-HT1D receptor (5-Hydroxytryptamine receptors)1992Proceedings of the National Academy of Sciences of the United States of America, Apr-15, Volume: 89, Issue:8
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
AID1346603Human 5-ht1e receptor (5-Hydroxytryptamine receptors)1996Journal of neurochemistry, Nov, Volume: 67, Issue:5
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
AID4788Binding affinity at 5-hydroxytryptamine 2 receptor from rat frontal cortex homogenates by [3H]-spiperone displacement.1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
AID3674Tested for its binding affinity towards 5-hydroxytryptamine 1 receptor in rat cortical membrane homogenates using radioligand ([3H]5-HT) binding assay.1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
AID224286Inhibition of p56 lck autophosphorylation, gamma-[33P]ATP incorporation (Inactive)1998Bioorganic & medicinal chemistry letters, Mar-17, Volume: 8, Issue:6
1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase.
AID233089Ratio of affinity towards 5-HT1 to 5-HT2 receptor1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.94)18.7374
1990's8 (23.53)18.2507
2000's5 (14.71)29.6817
2010's17 (50.00)24.3611
2020's3 (8.82)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.44

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 Index31.44 (24.57)
Research Supply Index3.58 (2.92)
Research Growth Index5.36 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.86%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (97.14%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]