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FUMITREMORGIN C

CAS No.:
118974-02-0
Catalog Number:
AG008Y1Y
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98%
1 week
United States
$418
- +
Product Description
Catalog Number:
AG008Y1Y
Chemical Name:
FUMITREMORGIN C
CAS Number:
118974-02-0
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
MDL Number:
MFCD08702652
IUPAC Name:
(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione
InChI:
InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
InChI Key:
DBEYVIGIPJSTOR-FHWLQOOXSA-N
SMILES:
COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
NSC Number:
719655
Properties
Complexity:
703  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
379.19g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
379.46g/mol
Monoisotopic Mass:
379.19g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
65.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3  
Literature
Title Journal
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Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus. Journal of natural products 20120427
Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities. Journal of agricultural and food chemistry 20120404
Serum-dependent export of protoporphyrin IX by ATP-binding cassette transporter G2 in T24 cells. Molecular and cellular biochemistry 20111201
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Differential inhibition of murine Bcrp1/Abcg2 and human BCRP/ABCG2 by the mycotoxin fumitremorgin C. European journal of pharmacology 20101010
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Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties. British journal of pharmacology 20091001
Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. American journal of physiology. Gastrointestinal and liver physiology 20090801
Bioactive alkaloids from endophytic Aspergillus fumigatus. Journal of natural products 20090401
Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. Chembiochem : a European journal of chemical biology 20090323
Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar. Journal of medicinal chemistry 20090226
ABCG2 is expressed in late spermatogenesis and is associated with the acrosome. Biochemical and biophysical research communications 20090109
Molecular expression and functional evidence of a drug efflux pump (BCRP) in human corneal epithelial cells. Current eye research 20090101
Application and limitation of inhibitors in drug-transporter interactions studies. International journal of pharmaceutics 20080522
Constitutive overexpression of P-glycoprotein, rather than breast cancer resistance protein or organic cation transporter 1, contributes to acquisition of imatinib-resistance in K562 cells. Pharmaceutical research 20080401
The breast cancer resistance protein (Bcrp1/Abcg2) limits fetal distribution of glyburide in the pregnant mouse: an Obstetric-Fetal Pharmacology Research Unit Network and University of Washington Specialized Center of Research Study. Molecular pharmacology 20080301
Functionalized chalcones as selective inhibitors of P-glycoprotein and breast cancer resistance protein. Bioorganic & medicinal chemistry 20080101
Porphyrin homeostasis maintained by ABCG2 regulates self-renewal of embryonic stem cells. PloS one 20080101
Expression of the ATP-binding cassette membrane transporter, ABCG2, in human and rodent brain microvessel endothelial and glial cell culture systems. Pharmaceutical research 20070701
C421 allele-specific ABCG2 gene amplification confers resistance to the antitumor triazoloacridone C-1305 in human lung cancer cells. Biochemical pharmacology 20070630
Energy transfer to analyse membrane-integrated mitoxantrone in BCRP-overexpressed cells. Journal of photochemistry and photobiology. B, Biology 20070525
Progesterone inhibits folic acid transport in human trophoblasts. The Journal of membrane biology 20070401
Zebrafish kidney marrow contains ABCG2-dependent side population cells exhibiting hematopoietic stem cell properties. Differentiation; research in biological diversity 20070301
Absorption of folate by Caco-2 cells is not affected by high glucose concentration. European journal of pharmacology 20061203
Complex interaction of BCRP/ABCG2 and imatinib in BCR-ABL-expressing cells: BCRP-mediated resistance to imatinib is attenuated by imatinib-induced reduction of BCRP expression. Blood 20060715
Expression and functional activity of breast cancer resistance protein (BCRP, ABCG2) transporter in the human choriocarcinoma cell line BeWo. Clinical and experimental pharmacology & physiology 20060101
Piperazinobenzopyranones and phenalkylaminobenzopyranones: potent inhibitors of breast cancer resistance protein (ABCG2). Journal of medicinal chemistry 20051117
Breast cancer resistance protein-mediated efflux of androgen in putative benign and malignant prostate stem cells. Cancer research 20050801
ABCG2-mediated transport of photosensitizers: potential impact on photodynamic therapy. Cancer biology & therapy 20050201
An improved definition of mouse mammary epithelial side population cells. Cytotherapy 20050101
Polyphasic taxonomy of Aspergillus fumigatus and related species. Mycologia 20050101
Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites. Journal of biotechnology 20041109
Liquid chromatography method for the quantitation of the breast cancer resistance protein ABCG2 inhibitor fumitremorgin C and its chemical analogues in mouse plasma and tissues. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040805
Fumagiringillin, a new fumagillin derivative from a strain of the fungus Aspergillus fumigatus. Journal of natural products 20040801
Broad-spectrum modulation of ATP-binding cassette transport proteins by the taxane derivatives ortataxel (IDN-5109, BAY 59-8862) and tRA96023. Cancer chemotherapy and pharmacology 20040501
Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Molecular pharmacology 20040501
Single amino acid substitutions in the transmembrane domains of breast cancer resistance protein (BCRP) alter cross resistance patterns in transfectants. International journal of cancer 20031210
The role of breast cancer resistance protein in acute lymphoblastic leukemia. Clinical cancer research : an official journal of the American Association for Cancer Research 20031101
Breast cancer resistance protein exports sulfated estrogens but not free estrogens. Molecular pharmacology 20030901
Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer research 20030901
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Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Molecular pharmacology 20030101
Isolation and toxigenicity of Aspergillus fumigatus from moldy silage. Mycopathologia 20030101
Penicillium digitatum metabolites on synthetic media and citrus fruits. Journal of agricultural and food chemistry 20021023
Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C. Molecular cancer therapeutics 20020401
Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochemical and biophysical research communications 20010706
Inhibition of BCRP-mediated drug efflux by fumitremorgin-type indolyl diketopiperazines. Bioorganic & medicinal chemistry letters 20010108
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Properties