retrorsine: RN given refers to cpd without isomeric designation; structure
ID Source | ID |
---|---|
PubMed CID | 5281743 |
CHEMBL ID | 496894 |
CHEBI ID | 8822 |
SCHEMBL ID | 133058 |
MeSH ID | M0044322 |
Synonym |
---|
senecionan-11,16-dione, 12,18-dihydroxy- |
12,18-dihydroxy-senecionan-11,16-dione |
3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione |
hsdb 3530 |
trans-15-ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine |
ccris 4338 |
nsc 107659 |
MLS002153926 |
smr001233270 |
BRD-K42142750-001-04-9 |
BRD-K42142750-001-01-5 |
(15z)-12,18-dihydroxysenecionan-11,16-dione |
BSPBIO_000634 |
PRESTWICK_562 |
PRESTWICK2_000637 |
BPBIO1_000698 |
PRESTWICK3_000637 |
retrorsin |
480-54-6 |
retrorsine |
nsc-107659 |
cis-retronecic acid ester of retronecine |
(z)-ethylidene-hydroxy-(hydroxymethyl)-methyl-[?]dione |
beta-longilobine |
12,18-dihydroxysenecionan-11,16-dione |
retrorsine, >=90% (hplc) |
NCGC00142486-03 |
HMS1545M22 |
HMS1569P16 |
HMS2096P16 |
CHEMBL496894 |
HMS2231J18 |
(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3z,5r,6s,14ar,14br)- |
unii-xj86xwl8iy |
xj86xwl8iy , |
retrorsine [hsdb] |
retrorsine [iarc] |
retrorsine [mi] |
CCG-208491 |
SCHEMBL133058 |
CHEBI:8822 , |
AKOS024282552 |
BCJMNZRQJAVDLD-CQRYIUNCSA-N |
retrorcine |
DTXSID6021242 |
SR-01000841220-3 |
sr-01000841220 |
(1r,4z,6r,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0??,??]heptadec-11-ene-3,8-dione |
(5r,6s,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione |
Q27108154 |
MS-25432 |
CS-0062871 |
HY-N6638 |
retrorsine 100 microg/ml in water |
Retrorsine (RTS) is a pyrrolizidine alkaloid (PA) found in herbal supplements and medicines, food and livestock feed. Retrorsine is a representative hepatotoxic and carcinogenic PA.
Retrorsine has been used extensively to inhibit proliferation of resident hepatocytes in various transplantation models. It has no effect on mouse hepatocyte proliferation.
Excerpt | Reference | Relevance |
---|---|---|
"Retrorsine has been used extensively to inhibit proliferation of resident hepatocytes in various transplantation models. " | ( Monocrotaline, an alternative to retrorsine-based hepatocyte transplantation in rodents. Fisher, SH; Petersen, BE; Witek, RP, 2005) | 2.05 |
"Retrorsine has no effect on mouse hepatocyte proliferation." | ( Effects of retrorsine on mouse hepatocyte proliferation after liver injury. Chu, JX; Liu, AL; Wang, Q; Zhou, XF, 2006) | 2.17 |
Excerpt | Reference | Relevance |
---|---|---|
"Retrorsine was used to inhibit endogenous hepatocyte proliferation, before inducing acute liver failure by carbon tetrachloride. " | ( Liver regeneration in a retrorsine/CCl4-induced acute liver failure model: do bone marrow-derived cells contribute? Aselmann, H; Bahlmann, FH; Dahlke, MH; Jäger, MD; Klempnauer, J; Neipp, M; Piso, P; Popp, FC; Schlitt, HJ, 2003) | 2.07 |
Retrorsine crosslinks host hepatocyte DNA and prevents proliferation after partial hepatectomy (PH), allowing selective expansion of transplanted progenitors. Treated with retrorsine, HSEC-CYP3A4 cells showed significantly reduced cell viability.
The aim of this study was to explore the characteristics of developmental toxicity and fetal hepatotoxicity induced by retrorsine (RTS, a typcial toxic PA) and the underlying mechanism. The results of hepatotoxic study showed that 15-h overnight fasting significantly exacerbated the hepatotoxicity of retrorsine in fasted rats.
Excerpt | Reference | Relevance |
---|---|---|
" The oral bioavailability of URM in female rats (81." | ( Quantification of Usaramine and its N-Oxide Metabolite in Rat Plasma Using Liquid Chromatography-Tandem Mass Spectrometry. Lin, F; Liu, J; Ma, Y; Pan, A; Ye, Y, 2022) | 0.72 |
Dose-response studies enabling the derivation of a point of departure including a benchmark dose for risk assessment of retrorsine in humans and animals are not available. In the present study, the correlations among the PA-derived liver DNA adducts, liver protein adductS, and serum protein adductions in retrorsin-treated mice under different dosage regimens were studied.
Class | Description |
---|---|
macrolide | A macrocyclic lactone with a ring of twelve or more members derived from a polyketide. |
[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) |
---|---|---|---|---|---|---|---|
ATAD5 protein, partial | Homo sapiens (human) | Potency | 4.4668 | 0.0041 | 10.8903 | 31.5287 | AID504467 |
TDP1 protein | Homo sapiens (human) | Potency | 7.7536 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 50.1187 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
chromobox protein homolog 1 | Homo sapiens (human) | Potency | 100.0000 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
transcriptional regulator ERG isoform 3 | Homo sapiens (human) | Potency | 11.2202 | 0.7943 | 21.2757 | 50.1187 | AID624246 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal 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. |
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. |
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. |
AID651635 | Viability Counterscreen for 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. |
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. |
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
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. |
AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & 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. |
AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 8 (5.30) | 18.7374 |
1990's | 29 (19.21) | 18.2507 |
2000's | 46 (30.46) | 29.6817 |
2010's | 49 (32.45) | 24.3611 |
2020's | 19 (12.58) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (27.17) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 1 (0.64%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 155 (99.36%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |