dibromophakellin: an alpha2B receptor agonist; isolated from Acanthella costata and Pseudoaxinyssa cantharella; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
(-)-dibromophakellin : An alkaloid isolated from the marine sponge Phakellia flabellata and Acanthella costata. It acts as an alpha2B adrenoceptor agonist. [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]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Acanthella | genus | [no description available] | Melastomataceae | A plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida composed of tropical plants with parallel-nerved leaves.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 42636938 |
| CHEMBL ID | 447696 |
| CHEBI ID | 65762 |
| MeSH ID | M0536211 |
| Synonym |
|---|
| bdbm50250521 |
| (-)-dibromophakellin |
| CHEMBL447696 , |
| (+/-)-dibromophakellin |
| dibromophakellin |
| chebi:65762 , |
| (3ar,12as)-2-amino-10,11-dibromo-1,5,6,12a-tetrahydro-4h,8h-imidazo[4,5-b]dipyrrolo[1,2-a:1',2'-d]pyrazin-8-one |
| dibromophakellin - casmi2016 category 1 - challenge 1 |
| Q27134247 |
| DTXSID301020634 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "(±)-Dibromophakellin has been synthesized in two steps from a known alkene intermediate. " | ( Total synthesis of the natural product (±)-dibromophakellin and analogues. Hewlett, NM; Tepe, JJ, 2011) | 1.19 |
| Role | Description |
|---|---|
| alpha-adrenergic agonist | An agent that selectively binds to and activates alpha-adrenergic receptors. |
| marine metabolite | Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. |
| animal metabolite | Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. |
| [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 |
|---|---|
| guanidines | Any organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas. |
| alkaloid | Any of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids. |
| organobromine compound | A compound containing at least one carbon-bromine bond. |
| [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) |
|---|---|---|---|---|---|---|---|
| Alpha-2B adrenergic receptor | Homo sapiens (human) | EC50 (µMol) | 4.2000 | 0.0005 | 1.3644 | 6.7100 | AID416324 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| alpha2-adrenergic receptor activity | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| protein binding | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| epinephrine binding | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| cytosol | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| plasma membrane | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| cell surface | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| intracellular membrane-bounded organelle | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| plasma membrane | Alpha-2B adrenergic receptor | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID416324 | Agonist activity at human adrenergic alpha2B receptor expressed in HEK293 cells coexpressing Gqi5 protein by FLIPR assay | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | (-)-Dibromophakellin: an alpha2B adrenoceptor agonist isolated from the Australian marine sponge, Acanthella costata. |
| AID671270 | Inhibition of chymotryptic-like of purified human 20S proteasome using Suc-LLVY-AMC as substrate after 30 mins by fluorescence assay | 2012 | Journal of natural products, May-25, Volume: 75, Issue:5 | Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome. |
| AID402506 | Cytotoxicity against human OVCAR-3 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| AID671271 | Inhibition of caspase-like of purified human 20S proteasome using Z-LLE-AMC as substrate after 30 mins by fluorescence assay | 2012 | Journal of natural products, May-25, Volume: 75, Issue:5 | Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome. |
| AID671272 | Inhibition of tryptic-like of purified human 20S proteasome using Boc-LRR-AMC as substrate after 30 mins by fluorescence assay | 2012 | Journal of natural products, May-25, Volume: 75, Issue:5 | Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome. |
| AID402508 | Cytotoxicity against human A498 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| AID402509 | Cytotoxicity against human H460 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| AID671273 | Inhibition of chymotryptic-like of purified human 20S immunoproteasome | 2012 | Journal of natural products, May-25, Volume: 75, Issue:5 | Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome. |
| AID402507 | Cytotoxicity against human SF295 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| AID402510 | Cytotoxicity against human KM20L2 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| AID402511 | Cytotoxicity against human SK-MEL-5 cells by SRB assay | 1997 | Journal of natural products, Feb, Volume: 60, Issue:2 | Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana. |
| [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 (12.50) | 18.2507 |
| 2000's | 2 (25.00) | 29.6817 |
| 2010's | 5 (62.50) | 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 (12.66) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (12.50%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (87.50%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||