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12772-57-5 | 6H-Oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione, 8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,2Z,4E,14R,15aR)-
CAS No: 12772-57-5 Catalog No: AG000XCJ MDL No:MFCD06795865
Product Description
Catalog Number:
AG000XCJ
Chemical Name:
6H-Oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione, 8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,2Z,4E,14R,15aR)-
CAS Number:
12772-57-5
Molecular Formula:
C18H17ClO6
Molecular Weight:
364.7770
MDL Number:
MFCD06795865
IUPAC Name:
(4R,6R,8R,9Z,11E)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
InChI:
InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1
InChI Key:
WYZWZEOGROVVHK-GTMNPGAYSA-N
SMILES:
C[C@@H]1C[C@H]2O[C@@H]2/C=C\C=C\C(=O)Cc2c(C(=O)O1)c(O)cc(c2Cl)O
UNII:
I60EH8GECX
Properties
Complexity:
588
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
2
Exact Mass:
364.071g/mol
Formal Charge:
0
Heavy Atom Count:
25
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
364.778g/mol
Monoisotopic Mass:
364.071g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
96.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.4
Literature
| Title | Journal |
|---|---|
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| cAMP-induced auditory supporting cell proliferation is mediated by ERK MAPK signaling pathway. | Journal of the Association for Research in Otolaryngology : JARO 20100601 |
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| Crystal structure of an intact type II DNA topoisomerase: insights into DNA transfer mechanisms. | Structure (London, England : 1993) 20080301 |
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| Divergent synthesis of a pochonin library targeting HSP90 and in vivo efficacy of an identified inhibitor. | Angewandte Chemie (International ed. in English) 20080101 |
| The stress responsive and morphologically regulated hsp90 gene from Paracoccidioides brasiliensis is essential to cell viability. | BMC microbiology 20080101 |
| Radicicol-mediated inhibition of Bcr-Abl in K562 cells induced p38-MAPK dependent erythroid differentiation and PU.1 down-regulation. | BioFactors (Oxford, England) 20080101 |
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| hsp90 is required for heme binding and activation of apo-neuronal nitric-oxide synthase: geldanamycin-mediated oxidant generation is unrelated to any action of hsp90. | The Journal of biological chemistry 20020607 |
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| Radicicol represses the transcriptional function of the estrogen receptor by suppressing the stabilization of the receptor by heat shock protein 90. | Molecular and cellular endocrinology 20020225 |
| A radicicol derivative, KF58333, inhibits expression of hypoxia-inducible factor-1alpha and vascular endothelial growth factor, angiogenesis and growth of human breast cancer xenografts. | Japanese journal of cancer research : Gann 20011201 |
| NO/cGMP signaling and HSP90 activity represses metamorphosis in the sea urchin Lytechinus pictus. | The Biological bulletin 20011201 |
| Stereospecific antitumor activity of radicicol oxime derivatives. | Cancer chemotherapy and pharmacology 20011201 |
| Concise asymmetric syntheses of radicicol and monocillin I. | Journal of the American Chemical Society 20011107 |
| Radicicol suppresses transformation and restores tropomyosin-2 expression in both ras- and MEK-transformed cells without inhibiting the Raf/MEK/ERK signaling cascade. | Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research 20011101 |
| Radicicol binding to Swo1/Hsp90 and inhibition of growth of specific temperature-sensitive cell cycle mutants of fission yeast. | Bioscience, biotechnology, and biochemistry 20011101 |
| Suppression of IL-8 gene expression by radicicol is mediated through the inhibition of ERK1/2 and p38 signaling and negative regulation of NF-kappaB and AP-1. | International immunopharmacology 20010901 |
| Effects of infusions of the tyrosine kinase inhibitor radicicol into the hippocampus on short- and long-term memory of the inhibitory avoidance task. | Behavioural pharmacology 20010701 |
| Radicicol and geldanamycin prevent neurotoxic effects of anti-cancer drugs on cultured embryonic sensory neurons. | Neuropharmacology 20010601 |
| UCS15A, a non-kinase inhibitor of Src signal transduction. | Oncogene 20010419 |
| Synergistic inhibition of the glucocorticoid receptor by radicicol and benzoquinone ansamycins. | Biological chemistry 20010301 |
| Androgen receptor signalling: comparative analysis of androgen response elements and implication of heat-shock protein 90 and 14-3-3eta. | Molecular and cellular endocrinology 20010227 |
| Inhibition of endotoxin-induced TNF-alpha production in macrophages by 5Z-7-oxo-zeaenol and other fungal resorcylic acid lactones. | International journal of immunopharmacology 19991201 |
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