dysiherbaine: an exitotoxic amino acid; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
dysiherbaine : A furopyran that is (3aR,7aR)-hexahydro-2H-furo[3,2-b]pyran substituted by carboxy, (2S)-2-amino-2-carboxyethyl, hydroxy and methylamino groups at positions 2, 2, 6, and 7, respectively (the 2R,3aR,6S,7R,7aR-stereoisomer). A convulsant isolated from the marine sponge Dysidea herbacea that has high affinity for kainate ionotropic glutamate receptors. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 9839436 |
| CHEMBL ID | 221142 |
| CHEBI ID | 197431 |
| SCHEMBL ID | 12409079 |
| MeSH ID | M0336037 |
| Synonym |
|---|
| (2r,3ar,6s,7r,7ar)-2-[(2s)-2-amino-2-carboxyethyl]-6-hydroxy-7-(methylamino)hexahydro-2h-furo[3,2-b]pyran-2-carboxylic acid |
| DYH , |
| CHEMBL221142 |
| CHEBI:197431 |
| dysiherbaine |
| 185245-55-0 |
| (-)-dysiherbaine |
| bdbm85740 |
| (2r,3ar,6s,7r,7ar)-2-[(2s)-2-amino-2-carboxyethyl]-6-hydroxy-7-(methylamino)-hexahydro-2h-furo[3,2-b]pyran-2-carboxylic acid |
| gtpl4185 |
| SCHEMBL12409079 |
| (2r,3ar,6s,7r,7ar)-2-[(2s)-2-amino-2-carboxyethyl]-6-hydroxy-7-(methylamino)-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylic acid |
| (2r,3ar,6s,7r,7ar)-2-[(2s)-2-amino-2-carboxyethyl]-6-hydroxy-7-(methylamino)hexahydro-2h-furo[3,2-b]pyran-2-carboxylic acid (non-preferred name) |
| Q27077134 |
Dysiherbaine (DH) is a marine sponge-derived amino acid that causes seizures upon injection into mice. It is a new excitotoxic amino acid which was recently isolated from the water extract of a certain sponge.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Dysiherbaine (DH) is a marine sponge-derived amino acid that causes seizures upon injection into mice. " | ( Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. Contractor, A; Ghetti, A; Green, T; Kamiya, H; Oiwa, C; Sakai, R; Shimamoto, K; Swanson, GT; Tamura-Horikawa, Y, 2001) | 1.99 |
| "Dysiherbaine is a new excitotoxic amino acid, which was recently isolated from the water extract of a certain sponge." | ( [Effects of a new excitotoxic amino acid, dysiherbaine, on cultured Müller cells]. Minei, R, 1999) | 1.29 |
| "Dysiherbaine is a new excitotoxic amino acid, which was recently isolated from the liquid extract of a certain sponge." | ( Effects of a new excitotoxic amino acid, dysiherbaine, on cultured Müller cells. Minei, R, ) | 1.12 |
A dysiherbaine-induced increase in [Ca2+]i following preincubation of the NMDA glutamate receptor antagonist, (5 R, 10 S)-(+)-5-methyl-10, 11-dihydro-5 H-dibenzo [a, d] cyclohepten-5, 10-imine hydrogen maleate (MK 801) was seen in the same number of Müller cells as without the antagonist.
| Excerpt | Reference | Relevance |
|---|---|---|
| "A dysiherbaine-induced increase in [Ca2+]i following preincubation of the NMDA glutamate receptor antagonist, (5 R, 10 S)-(+)-5-methyl-10, 11-dihydro-5 H-dibenzo [a, d] cyclohepten-5, 10-imine hydrogen maleate (MK 801) was seen in the same number of Müller cells as without the antagonist." | ( [Effects of a new excitotoxic amino acid, dysiherbaine, on cultured Müller cells]. Minei, R, 1999) | 1.13 |
| "A dysiherbaine-induced increase in [Ca(2+)](i) following preincubation of the NMDA glutamate receptor antagonist, (5R,10S)-(+)-5-methyl-10,11-dyhydro-5H-dibenzo [a,d] cyclohepten-5, 10-imine hydrogen maleate (MK 801) was seen in the same number of Müller cells with and without the antagonist." | ( Effects of a new excitotoxic amino acid, dysiherbaine, on cultured Müller cells. Minei, R, ) | 0.96 |
| Role | Description |
|---|---|
| excitatory amino acid agonist | An agent that binds to and activates excitatory amino acid receptors. |
| animal metabolite | Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. |
| marine metabolite | Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. |
| neurotoxin | A poison that interferes with the functions of the nervous system. |
| [role 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] | |
| Class | Description |
|---|---|
| amino dicarboxylic acid | |
| furopyran | Any organic heterobicyclic compound containing ortho-fused furan and pyran rings. |
| secondary amino compound | A compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups. |
| hydroxy carboxylic acid | Any carboxylic acid with at least one hydroxy group. |
| [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 | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Glutamate receptor ionotropic, kainate 1 | Homo sapiens (human) | Ki | 0.0007 | 0.0007 | 1.7508 | 4.8000 | AID1325014 |
| Glutamate receptor ionotropic, kainate 2 | Homo sapiens (human) | Ki | 0.0012 | 0.0012 | 0.3344 | 1.1060 | AID1325015 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1346642 | Rat GluK1 (Ionotropic glutamate receptors) | 2001 | The Journal of pharmacology and experimental therapeutics, Feb, Volume: 296, Issue:2 | Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. |
| AID1346544 | Rat GluK2 (Ionotropic glutamate receptors) | 2001 | The Journal of pharmacology and experimental therapeutics, Feb, Volume: 296, Issue:2 | Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. |
| AID1325015 | Displacement of [3H]kianic acid from recombinant GluK2 kainate receptor (unknown origin) expressed in HEK293 cell membranes measured after 1 hr | 2016 | Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21 | A monocyclic neodysiherbaine analog: Synthesis and evaluation. |
| AID276397 | Displacement of [3H]kainic acid from Kainate receptor in rat synaptic membrane | 2006 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 16, Issue:22 | Design, total synthesis, and biological evaluation of neodysiherbaine A derivative as potential probes. |
| AID276395 | Epileptogenic activity in mouse, icv | 2006 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 16, Issue:22 | Design, total synthesis, and biological evaluation of neodysiherbaine A derivative as potential probes. |
| AID276396 | Displacement of [3H]AMPA from AMPA receptor in rat synaptic membrane | 2006 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 16, Issue:22 | Design, total synthesis, and biological evaluation of neodysiherbaine A derivative as potential probes. |
| AID1325014 | Displacement of [3H]kianic acid from recombinant GluK1 kainate receptor (unknown origin) expressed in HEK293 cell membranes measured after 1 hr | 2016 | Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21 | A monocyclic neodysiherbaine analog: Synthesis and evaluation. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (3.85) | 18.2507 |
| 2000's | 19 (73.08) | 29.6817 |
| 2010's | 6 (23.08) | 24.3611 |
| 2020's | 0 (0.00) | 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 (12.02) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (7.41%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 25 (92.59%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||