(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.
ID Source | ID |
---|---|
PubMed CID | 440990 |
CHEMBL ID | 156383 |
CHEBI ID | 27702 |
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)- |
Class | Description |
---|---|
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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 9.4662 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 39.8107 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
glp-1 receptor, partial | Homo sapiens (human) | Potency | 6.3002 | 0.0184 | 6.8060 | 14.1254 | AID624172; AID624417; AID743262 |
WRN | Homo sapiens (human) | Potency | 79.4328 | 0.1683 | 31.2583 | 100.0000 | AID651768 |
phosphopantetheinyl transferase | Bacillus subtilis | Potency | 70.7946 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
TDP1 protein | Homo sapiens (human) | Potency | 19.4763 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 17.7828 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
apical membrane antigen 1, AMA1 | Plasmodium falciparum 3D7 | Potency | 2.5119 | 0.7079 | 12.1943 | 39.8107 | AID720542 |
pyruvate kinase | Leishmania mexicana mexicana | Potency | 0.5012 | 0.3981 | 13.7447 | 31.6228 | AID1721; AID1722 |
euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 39.8107 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
lysosomal alpha-glucosidase preproprotein | Homo sapiens (human) | Potency | 1.4125 | 0.0366 | 19.6376 | 50.1187 | AID2100 |
chromobox protein homolog 1 | Homo sapiens (human) | Potency | 79.4328 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 50.3126 | 0.0501 | 27.0736 | 89.1251 | AID588590; AID720496 |
nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 35.4813 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
geminin | Homo sapiens (human) | Potency | 29.0929 | 0.0046 | 11.3741 | 33.4983 | AID624296; AID624297 |
DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 89.1251 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
Endothelin receptor type B | Rattus norvegicus (Norway rat) | Potency | 0.5012 | 0.5623 | 15.1609 | 31.6228 | AID1721 |
Endothelin-1 receptor | Rattus norvegicus (Norway rat) | Potency | 0.5012 | 0.5623 | 15.1609 | 31.6228 | AID1721 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
integrase, partial | Human immunodeficiency virus 1 | IC50 (µMol) | 17.7010 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
lens epithelium-derived growth factor p75 | Homo sapiens (human) | IC50 (µMol) | 17.7010 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
alkaline phosphatase, tissue-nonspecific isozyme isoform 1 preproprotein | Homo sapiens (human) | IC50 (µMol) | 10.1000 | 0.1250 | 16.2603 | 74.8000 | AID488906 |
intestinal alkaline phosphatase precursor | Mus musculus (house mouse) | IC50 (µMol) | 8.0600 | 0.2590 | 11.8708 | 60.3000 | AID488785 |
Vif | Human immunodeficiency virus 1 | IC50 (µMol) | 9.7700 | 0.2700 | 34.0015 | 100.0000 | AID1117319 |
high affinity choline transporter 1 isoform a | Homo sapiens (human) | IC50 (µMol) | 0.4703 | 0.0003 | 6.2102 | 28.8403 | AID504840 |
DNA dC->dU-editing enzyme APOBEC-3G isoform 1 | Homo sapiens (human) | IC50 (µMol) | 9.7700 | 0.2700 | 26.3638 | 100.0000 | AID1117319 |
Beta-2 adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 30.0000 | 0.0005 | 0.3546 | 1.6000 | AID41753 |
Alpha-1B adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0001 | 0.9490 | 10.0000 | AID33138 |
Beta-1 adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 30.0000 | 0.0000 | 0.6673 | 10.0000 | AID41753 |
Alpha-2B adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0000 | 0.9296 | 10.0000 | AID33138 |
Alpha-2C adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0000 | 0.9708 | 10.0000 | AID33138 |
Alpha-2A adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0000 | 0.9375 | 10.0000 | AID33138 |
Alpha-1D adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0000 | 0.5751 | 10.0000 | AID33138 |
Beta-3 adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 30.0000 | 0.0005 | 0.3367 | 1.6000 | AID41753 |
Adenosine receptor A2a | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0002 | 1.4940 | 10.0000 | AID33138 |
Alpha-1A adrenergic receptor | Rattus norvegicus (Norway rat) | Ki | 25.0000 | 0.0000 | 0.9650 | 10.0000 | AID33138 |
large T antigen | Betapolyomavirus macacae | IC50 (µMol) | 9.0600 | 0.1600 | 24.9724 | 100.0000 | AID1903 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
alkaline phosphatase, intestinal | Homo sapiens (human) | EC50 (µMol) | 100.0000 | 0.2570 | 26.8395 | 81.0000 | AID488873 |
alkaline phosphatase, germ cell type preproprotein | Homo sapiens (human) | EC50 (µMol) | 100.0000 | 0.5500 | 33.7339 | 74.0000 | AID488878 |
POsterior Segregation | Caenorhabditis elegans | EC50 (µMol) | 6.3590 | 2.2010 | 47.1808 | 186.6810 | AID1964 |
Sodium-dependent noradrenaline transporter | Homo sapiens (human) | EC50 (µMol) | 5.4310 | 0.0820 | 31.0243 | 168.9080 | AID1960 |
Zinc finger protein mex-5 | Caenorhabditis elegans | EC50 (µMol) | 5.4310 | 0.0820 | 33.5679 | 168.9080 | AID1960 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
plasma membrane | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
cell surface | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
membrane | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
neuronal cell body membrane | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
presynaptic membrane | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
plasma membrane | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
axon | Sodium-dependent noradrenaline transporter | Homo sapiens (human) |
Golgi membrane | Adenosine receptor A2a | Rattus norvegicus (Norway rat) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID63017 | Inhibition of [3H]spiroperidol binding to dopamine receptor from rat striatum membranes | 1980 | Journal of medicinal chemistry, Jun, Volume: 23, Issue:6 | Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines. |
AID41753 | Inhibition of [3H]dihydroalprenolol binding to Beta adrenergic receptor from rat cerebral cortical membranes | 1980 | Journal of medicinal chemistry, Jun, Volume: 23, Issue:6 | Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines. |
AID33138 | Inhibition of [3H]WB-4101 binding to alpha adrenergic receptor from rat cerebral cortical membranes | 1980 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (16.67) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (16.67) | 29.6817 |
2010's | 3 (50.00) | 24.3611 |
2020's | 1 (16.67) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (12.19) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 6 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |