Page last updated: 2024-12-08

(R)-norlaudanosoline

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

(R)-norlaudanosoline is a **tetrahydroisoquinoline alkaloid** that is naturally found in plants like *Papaver somniferum* (opium poppy).

**Here's why it's important for research:**

* **Precursor to key compounds:** (R)-norlaudanosoline acts as a **precursor** in the biosynthesis of many important natural products, including:
* **Morphine alkaloids:** These are potent analgesics with significant medical uses.
* **Papaverine:** This is a vasodilator used to treat various conditions.
* **Thebaine:** This is a synthetic precursor to many opioid analgesics like oxycodone and hydrocodone.
* **Biological activity:**
* (R)-norlaudanosoline itself exhibits **biological activity** in its own right. It has been shown to possess **antioxidant and anti-inflammatory properties**.
* It can also act as an **inhibitor** of certain enzymes, potentially affecting various biological processes.
* **Research tool:** (R)-norlaudanosoline is a valuable **research tool** for studying:
* **Biosynthetic pathways:** Understanding how (R)-norlaudanosoline is synthesized and converted into other compounds can lead to novel approaches to drug development.
* **Biological activity:** Studying the effects of (R)-norlaudanosoline on different biological systems can provide insights into its potential therapeutic applications.
* **Enzyme inhibition:** Research using (R)-norlaudanosoline can help identify and develop new enzyme inhibitors with therapeutic value.

**Current research is focused on:**

* **Developing synthetic routes** to (R)-norlaudanosoline, which would be a more efficient way to obtain this compound for research purposes.
* **Investigating the potential applications of (R)-norlaudanosoline** in various fields, including medicine, agriculture, and materials science.
* **Understanding the mechanisms of action** of (R)-norlaudanosoline to further explore its potential therapeutic uses.

Overall, (R)-norlaudanosoline is a fascinating molecule with diverse biological activities and potential applications, making it a valuable subject for continued research efforts.

Cross-References

ID SourceID
PubMed CID440990
CHEMBL ID156383
CHEBI ID27702

Synonyms (23)

Synonym
(r)-norlaudanosoline
C06351
smr000544174
MLS001216445
CHEBI:27702 ,
(1r)-1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
(1r)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
CHEMBL156383 ,
cid_440990
bdbm50027326
HMS2852J05
NCGC00246226-01
REGID_FOR_CID_440990
AKOS030499101
57073-16-2
Q27103270
6,7-isoquinolinediol, 1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-, (1r)-
unii-zdc4p56aqs
(r)-(+)-tetrahydropapaveroline
zdc4p56aqs ,
(+)-tetrahydropapaveroline
tetrahydropapaveroline, (+)-
1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol, (r)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
norlaudanosoline
[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 (44)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency9.46620.003245.467312,589.2998AID2517
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency39.81070.631035.7641100.0000AID504339
glp-1 receptor, partialHomo sapiens (human)Potency6.30020.01846.806014.1254AID624172; AID624417; AID743262
WRNHomo sapiens (human)Potency79.43280.168331.2583100.0000AID651768
phosphopantetheinyl transferaseBacillus subtilisPotency70.79460.141337.9142100.0000AID1490
TDP1 proteinHomo sapiens (human)Potency19.47630.000811.382244.6684AID686978; AID686979
thioredoxin glutathione reductaseSchistosoma mansoniPotency17.78280.100022.9075100.0000AID485364
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency2.51190.707912.194339.8107AID720542
pyruvate kinaseLeishmania mexicana mexicanaPotency0.50120.398113.744731.6228AID1721; AID1722
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency39.81070.035520.977089.1251AID504332
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency1.41250.036619.637650.1187AID2100
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency50.31260.050127.073689.1251AID588590; AID720496
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2546
gemininHomo sapiens (human)Potency29.09290.004611.374133.4983AID624296; AID624297
DNA polymerase kappa isoform 1Homo sapiens (human)Potency89.12510.031622.3146100.0000AID588579
Endothelin receptor type BRattus norvegicus (Norway rat)Potency0.50120.562315.160931.6228AID1721
Endothelin-1 receptorRattus norvegicus (Norway rat)Potency0.50120.562315.160931.6228AID1721
[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)
integrase, partialHuman immunodeficiency virus 1IC50 (µMol)17.70100.07953.52039.9390AID1053171; AID1053172
lens epithelium-derived growth factor p75Homo sapiens (human)IC50 (µMol)17.70100.07953.52039.9390AID1053171; AID1053172
alkaline phosphatase, tissue-nonspecific isozyme isoform 1 preproproteinHomo sapiens (human)IC50 (µMol)10.10000.125016.260374.8000AID488906
intestinal alkaline phosphatase precursorMus musculus (house mouse)IC50 (µMol)8.06000.259011.870860.3000AID488785
VifHuman immunodeficiency virus 1IC50 (µMol)9.77000.270034.0015100.0000AID1117319
high affinity choline transporter 1 isoform aHomo sapiens (human)IC50 (µMol)0.47030.00036.210228.8403AID504840
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)IC50 (µMol)9.77000.270026.3638100.0000AID1117319
Beta-2 adrenergic receptorRattus norvegicus (Norway rat)Ki30.00000.00050.35461.6000AID41753
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00010.949010.0000AID33138
Beta-1 adrenergic receptorRattus norvegicus (Norway rat)Ki30.00000.00000.667310.0000AID41753
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00000.929610.0000AID33138
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00000.970810.0000AID33138
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00000.937510.0000AID33138
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00000.575110.0000AID33138
Beta-3 adrenergic receptorRattus norvegicus (Norway rat)Ki30.00000.00050.33671.6000AID41753
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki25.00000.00021.494010.0000AID33138
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)Ki25.00000.00000.965010.0000AID33138
large T antigenBetapolyomavirus macacaeIC50 (µMol)9.06000.160024.9724100.0000AID1903
[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)
alkaline phosphatase, intestinalHomo sapiens (human)EC50 (µMol)100.00000.257026.839581.0000AID488873
alkaline phosphatase, germ cell type preproproteinHomo sapiens (human)EC50 (µMol)100.00000.550033.733974.0000AID488878
POsterior SegregationCaenorhabditis elegansEC50 (µMol)6.35902.201047.1808186.6810AID1964
Sodium-dependent noradrenaline transporter Homo sapiens (human)EC50 (µMol)5.43100.082031.0243168.9080AID1960
Zinc finger protein mex-5Caenorhabditis elegansEC50 (µMol)5.43100.082033.5679168.9080AID1960
[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 (11)

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)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

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)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
AID63017Inhibition of [3H]spiroperidol binding to dopamine receptor from rat striatum membranes1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines.
AID41753Inhibition of [3H]dihydroalprenolol binding to Beta adrenergic receptor from rat cerebral cortical membranes1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines.
AID33138Inhibition of [3H]WB-4101 binding to alpha adrenergic receptor from rat cerebral cortical membranes1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

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

MetricThis Compound (vs All)
Research Demand Index12.19 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]