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119757-73-2 | 3-Furanpropanoic acid, 2,5-dihydro-β-hydroxy-4-methyl-2,5-dioxo-, (1R,2S,6S,7S,10S,12R,15E)-16-ethyl-3,7-dihydroxy-1,2,6,10,12-pentamethyl-5,14-dioxo-15,17-octadecadien-1-yl ester, (βR)-
CAS No: 119757-73-2 Catalog No: AG000PLG MDL No:
Product Description
Catalog Number:
AG000PLG
Chemical Name:
3-Furanpropanoic acid, 2,5-dihydro-β-hydroxy-4-methyl-2,5-dioxo-, (1R,2S,6S,7S,10S,12R,15E)-16-ethyl-3,7-dihydroxy-1,2,6,10,12-pentamethyl-5,14-dioxo-15,17-octadecadien-1-yl ester, (βR)-
CAS Number:
119757-73-2
Molecular Formula:
C33H50O10
Molecular Weight:
606.7441
IUPAC Name:
[(16E)-17-ethyl-4,8-dihydroxy-3,7,11,13-tetramethyl-6,15-dioxononadeca-16,18-dien-2-yl] 3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
InChI:
InChI=1S/C33H50O10/c1-9-24(10-2)15-25(34)14-19(4)13-18(3)11-12-26(35)21(6)28(37)16-27(36)20(5)23(8)42-30(39)17-29(38)31-22(7)32(40)43-33(31)41/h9,15,18-21,23,26-27,29,35-36,38H,1,10-14,16-17H2,2-8H3/b24-15-
InChI Key:
VAIBGAONSFVVKI-IWIPYMOSSA-N
SMILES:
CC/C(=C\C(=O)C[C@@H](C[C@H](CC[C@@H]([C@@H](C(=O)CC([C@@H]([C@H](OC(=O)C[C@H](C1=C(C)C(=O)OC1=O)O)C)C)O)C)O)C)C)/C=C
Properties
Complexity:
1090
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
606.34g/mol
Formal Charge:
0
Heavy Atom Count:
43
Hydrogen Bond Acceptor Count:
10
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
606.753g/mol
Monoisotopic Mass:
606.34g/mol
Rotatable Bond Count:
21
Topological Polar Surface Area:
165A^2
Undefined Atom Stereocenter Count:
8
Undefined Bond Stereocenter Count:
0
XLogP3:
4.7
Literature
| Title | Journal |
|---|---|
| Comparative toxicological study of the novel protein phosphatase inhibitor 19-Epi-okadaic acid in primary cultures of rat cerebellar cells. | Toxicological sciences : an official journal of the Society of Toxicology 20130401 |
| Biological activities of an engineered tautomycetin analogue via disruption of tmcR-encoding hydroxylase in Streptomyces sp. CK4412. | Journal of industrial microbiology & biotechnology 20121001 |
| Functional characterization of the genes tauO, tauK, and tauI in the biosynthesis of tautomycetin. | Journal of microbiology (Seoul, Korea) 20121001 |
| Cell surface expression of the major amyloid-β peptide (Aβ)-degrading enzyme, neprilysin, depends on phosphorylation by mitogen-activated protein kinase/extracellular signal-regulated kinase kinase (MEK) and dephosphorylation by protein phosphatase 1a. | The Journal of biological chemistry 20120824 |
| Functional characterization of ttnI completing the tailoring steps for tautomycetin biosynthesis in Streptomyces griseochromogenes. | Organic letters 20120302 |
| Identification and characterization of wblA-dependent tmcT regulation during tautomycetin biosynthesis in Streptomyces sp. CK4412. | Biotechnology advances 20120101 |
| Relationship between ATM and ribosomal protein S6 revealed by the chemical inhibition of Ser/Thr protein phosphatase type 1. | Bioscience, biotechnology, and biochemistry 20120101 |
| SHP2 is a target of the immunosuppressant tautomycetin. | Chemistry & biology 20110128 |
| Interrelationship between protein phosphatase 1 and TGF-{beta} in regulating motility and cytoskeletal architecture of endothelial cells. | Anticancer research 20101201 |
| Biochemical and structural characterization of the tautomycetin thioesterase: analysis of a stereoselective polyketide hydrolase. | Angewandte Chemie (International ed. in English) 20100802 |
| Functional characterization of TtnD and TtnF, unveiling new insights into tautomycetin biosynthesis. | Journal of the American Chemical Society 20100519 |
| The synergistic effect of Tautomycetin on Cyclosporine A-mediated immunosuppression in a rodent islet allograft model. | Molecular medicine (Cambridge, Mass.) 20100101 |
| Iminothiol/thiourea tautomeric equilibrium in thiourea lipids impacts DNA compaction by inducing a cationic nucleation for complex assembly. | Biophysical chemistry 20091101 |
| Functional expression of SCO7832 stimulates tautomycetin production via pathway-specific regulatory gene overexpression in Streptomyces sp. CK4412. | Journal of industrial microbiology & biotechnology 20090701 |
| Functional characterization of ttmM unveils new tautomycin analogs and insight into tautomycin biosynthesis and activity. | Organic letters 20090402 |
| Tautomycetin and tautomycin suppress the growth of medullary thyroid cancer cells via inhibition of glycogen synthase kinase-3beta. | Molecular cancer therapeutics 20090401 |
| Characterization of the tautomycetin biosynthetic gene cluster from Streptomyces griseochromogenes provides new insight into dialkylmaleic anhydride biosynthesis. | Journal of natural products 20090327 |
| Tautomycetin suppresses the TNFalpha/NF-kappaB pathway via inhibition of IKK activation. | International journal of oncology 20081101 |
| Identification of TmcN as a pathway-specific positive regulator of tautomycetin biosynthesis in Streptomyces sp. CK4412. | Microbiology (Reading, England) 20081001 |
| Uterine artery myosin phosphatase isoform switching and increased sensitivity to SNP in a rat L-NAME model of hypertension of pregnancy. | American journal of physiology. Cell physiology 20080201 |
| Isolation of the biosynthetic gene cluster for tautomycetin, a linear polyketide T cell-specific immunomodulator from Streptomyces sp. CK4412. | Microbiology (Reading, England) 20070401 |
| Small-molecule inhibitors of ser/thr protein phosphatases: specificity, use and common forms of abuse. | Methods in molecular biology (Clifton, N.J.) 20070101 |
| Tautomycetin inhibits growth of colorectal cancer cells through p21cip/WAF1 induction via the extracellular signal-regulated kinase pathway. | Molecular cancer therapeutics 20061201 |
| Effects of tautomycetin on proliferation and fibronectin secretion in vascular smooth muscle cells and glomerular mesangial cells. | Transplantation proceedings 20050501 |
| T Cell-specific immunosuppression using tautomycetin or PTD-conjugated protein drugs. | Yonsei medical journal 20041231 |
| Novel biologically active natural and unnatural products. | Current opinion in biotechnology 20031201 |
| Tautomycetin as a novel immunosuppressant in transplantation. | Transplantation proceedings 20030201 |
| Usage of tautomycetin, a novel inhibitor of protein phosphatase 1 (PP1), reveals that PP1 is a positive regulator of Raf-1 in vivo. | The Journal of biological chemistry 20030103 |
| Synthesis of specific protein phosphatase inhibitors, tautomycin and tautomycetin toward structure-activity relationship study. | Current medicinal chemistry 20021101 |
| [Structure and function of a novel PP-1 specific inhibitor, tautomycetin]. | Seikagaku. The Journal of Japanese Biochemical Society 20021101 |
| Tautomycetin is a novel and specific inhibitor of serine/threonine protein phosphatase type 1, PP1. | Biochemical and biophysical research communications 20010921 |
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