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15503-87-4 | [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-, (3E,5R,6S,14aR,14bR)-
CAS No: 15503-87-4 Catalog No: AG001NK9 MDL No:
Product Description
Catalog Number:
AG001NK9
Chemical Name:
[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-, (3E,5R,6S,14aR,14bR)-
CAS Number:
15503-87-4
Molecular Formula:
C18H25NO6
Molecular Weight:
351.3942
IUPAC Name:
(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
InChI:
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1
InChI Key:
BCJMNZRQJAVDLD-FXGRWVCYSA-N
SMILES:
C/C=C/1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
Properties
Complexity:
627
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
1
Exact Mass:
351.168g/mol
Formal Charge:
0
Heavy Atom Count:
25
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
351.399g/mol
Monoisotopic Mass:
351.168g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
96.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.6
Literature
| Title | Journal |
|---|---|
| Comparative Study of Hepatotoxicity of Pyrrolizidine Alkaloids Retrorsine and Monocrotaline. | Chemical research in toxicology 20170220 |
| Involvement of organic cation transporter 1 and CYP3A4 in retrorsine-induced toxicity. | Toxicology 20140801 |
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Hepatocyte senescence in vivo following preconditioning for liver repopulation. | Hepatology (Baltimore, Md.) 20120801 |
| Fetal liver-derived mesenchymal stromal cells augment engraftment of transplanted hepatocytes. | Cytotherapy 20120701 |
| Profiling of alkaloids and eremophilanes in miracle tea (Packera candidissima and P. bellidifolia) products. | Journal of natural products 20120525 |
| Growth ability and repopulation efficiency of transplanted hepatic stem cells, progenitor cells, and mature hepatocytes in retrorsine-treated rat livers. | Cell transplantation 20120101 |
| HSQC-1,1-ADEQUATE and HSQC-1,n-ADEQUATE: enhanced methods for establishing adjacent and long-range 13C-13C connectivity networks. | Journal of natural products 20111128 |
| [Developmental toxicity of retrorsine on mouse embryos in vitro]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110701 |
| The growth pattern of transplanted normal and nodular hepatocytes. | Histochemistry and cell biology 20110601 |
| Liver regeneration by small hepatocyte-like progenitor cells after necrotic injury by carbon tetrachloride in retrorsine-exposed rats. | Experimental and molecular pathology 20101001 |
| Cytokine-dependent activation of small hepatocyte-like progenitor cells in retrorsine-induced rat liver injury. | Experimental and molecular pathology 20100201 |
| Retrorsine, but not monocrotaline, is a mechanism-based inactivator of P450 3A4. | Chemico-biological interactions 20100105 |
| Endogenous and transplanted small hepatocytes in retrorsine-treated/partially hepatectomized rat liver show differences in growth, phenotype, and proximity to clusters of gamma-glutamyl transpeptidase-positive host hepatocytes. | The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20100101 |
| Hepatocyte transplantation and the differentiation fate of host oval cells in acute severe hepatic injury. | Cell transplantation 20100101 |
| Effects of bone marrow and hepatocyte transplantation on liver injury. | The Journal of surgical research 20091101 |
| Engraftment of syngeneic and allogeneic endothelial cells, hepatocytes and cholangiocytes into partially hepatectomized rats previously treated with mitomycin C. | Transplantation 20090827 |
| Generation of hepatocyte-like cells from in vitro transdifferentiated human fetal pancreas. | Cell transplantation 20090101 |
| Impaired hepatocyte regeneration in acute severe hepatic injury enhances effective repopulation by transplanted hepatocytes. | Cell transplantation 20090101 |
| Hepatocytes from fibrotic liver possess high growth potential in vivo. | Cell transplantation 20090101 |
| Direct in vivo cell lineage analysis in the retrorsine and 2AAF models of liver injury after genetic labeling in adult and newborn rats. | PloS one 20090101 |
| Low-dose recombinant human hepatocyte growth factor enhances effect of hepatocyte transplantation in rats treated with retrorsine. | Hepato-gastroenterology 20090101 |
| Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. | Toxicology letters 20080505 |
| Proliferation of L02 human hepatocytes in tolerized genetically immunocompetent rats. | World journal of gastroenterology 20080421 |
| Cells of origin of small hepatocyte-like progenitor cells in the retrorsine model of rat liver injury and regeneration. | Journal of hepatology 20080201 |
| Origin of small hepatocyte-like progenitor in retrorsine-treated rats. | Journal of hepatology 20080201 |
| Repopulation by endogenous hepatocytes does not reconstitute liver mass in rats treated with retrorsine. | Cell transplantation 20080101 |
| Bile duct destruction by 4,4'-diaminodiphenylmethane does not block the small hepatocyte-like progenitor cell response in retrorsine-exposed rats. | Hepatology (Baltimore, Md.) 20071101 |
| Senecio latifolius induces in vitro hepatocytotoxicity in a human cell line. | Canadian journal of physiology and pharmacology 20071101 |
| The toxicity of Senecio inaequidens DC. | Journal of the South African Veterinary Association 20070901 |
| Treatment with 2-AAF blocks the small hepatocyte-like progenitor cell response in retrorsine-exposed rats. | Journal of hepatology 20070601 |
| [The repopulation of human L02 hepatocytes in tolerant rats treated with retrorsine]. | Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology 20070301 |
| Cholangiocyte marker-positive and -negative fetal liver cells differ significantly in their ability to regenerate the livers of adult rats exposed to retrorsine. | Development (Cambridge, England) 20061101 |
| Effects of retrorsine on mouse hepatocyte proliferation after liver injury. | World journal of gastroenterology 20060307 |
| Liver repopulation trial using bone marrow cells in a retrorsine-induced chronic hepatocellular injury model. | Gastroenterologie clinique et biologique 20060301 |
| Isolation and characterization of bipotent liver progenitor cells from adult mouse. | Stem cells (Dayton, Ohio) 20060201 |
| The sources of parenchymal regeneration after chronic hepatocellular liver injury in mice. | Hepatology (Baltimore, Md.) 20060201 |
| Cyclin D1 is up-regulated in hepatocytes in vivo following cell-cycle block induced by retrorsine. | Journal of hepatology 20050901 |
| Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. | Cell proliferation 20050601 |
| Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. | International journal of environmental research and public health 20050501 |
| Human liver microsomal reduction of pyrrolizidine alkaloid N-oxides to form the corresponding carcinogenic parent alkaloid. | Toxicology letters 20050315 |
| GC/MS identification of toxic pyrrolizidine alkaloids in traditional remedies given to two sets of twins. | Annals of clinical biochemistry 20050301 |
| Monocrotaline, an alternative to retrorsine-based hepatocyte transplantation in rodents. | Cell transplantation 20050101 |
| Mature hepatocytes are the source of small hepatocyte-like progenitor cells in the retrorsine model of liver injury. | Journal of hepatology 20041101 |
| Molecular mechanisms of apoptosis in the liver of rats after portal branch ligation with and without retrorsine. | Laboratory investigation; a journal of technical methods and pathology 20040501 |
| Liver repopulation by c-Met-positive stem/progenitor cells isolated from the developing rat liver. | Hepato-gastroenterology 20040101 |
| Bone marrow progenitors are not the source of expanding oval cells in injured liver. | Stem cells (Dayton, Ohio) 20040101 |
| Liver regeneration in a retrorsine/CCl4-induced acute liver failure model: do bone marrow-derived cells contribute? | Journal of hepatology 20030901 |
| Retrorsine: a kinetic study of its influence on rat liver regeneration in the portal branch ligation model. | Journal of hepatology 20030701 |
| [Proliferation of retrorsine-treated SD rat immortalized hepatocytes after intrasplenic transplantation]. | Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20030601 |
| Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth. | Journal of chemical ecology 20020901 |
| Liver repopulation after cell transplantation in mice treated with retrorsine and carbon tetrachloride. | Transplantation 20020615 |
| Isolation, short-term culture, and transplantation of small hepatocyte-like progenitor cells from retrorsine-exposed rats. | Transplantation 20020427 |
| Stem cell properties and repopulation of the rat liver by fetal liver epithelial progenitor cells. | The American journal of pathology 20011001 |
| Correction of liver disease following transplantation of normal rat hepatocytes into Long-Evans Cinnamon rats modeling Wilson's disease. | Molecular therapy : the journal of the American Society of Gene Therapy 20010301 |
| Massive liver replacement by transplanted hepatocytes in the absence of exogenous growth stimuli in rats treated with retrorsine. | The American journal of pathology 20010201 |
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | Journal of natural products 19910101 |
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