Home Other Building Blocks Ergotaman-3',6',18-trione,12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'a)-

Ergotaman-3',6',18-trione,12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'a)-

CAS No.:
511-08-0
Catalog Number:
AG01CC7T
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG01CC7T
Chemical Name:
Ergotaman-3',6',18-trione,12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'a)-
CAS Number:
511-08-0
MDL Number:
MFCD00215848
IUPAC Name:
(6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
InChI:
InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1
InChI Key:
HEFIYUQVAZFDEE-MKTPKCENSA-N
EC Number:
208-120-7
UNII:
3E58HO2T0U
Properties
Complexity:
1270  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0
Exact Mass:
609.295g/mol
Formal Charge:
0
Heavy Atom Count:
45  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
609.727g/mol
Monoisotopic Mass:
609.295g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
118A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3  
Literature
Title Journal
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicological sciences : an official journal of the Society of Toxicology 20131201
Degradation and epimerization of ergot alkaloids after baking and in vitro digestion. Analytical and bioanalytical chemistry 20121101
Constriction of bovine vasculature caused by endophyte-infected tall fescue seed extract is similar to pure ergovaline. Journal of animal science 20120501
Permeability of ergot alkaloids across the blood-brain barrier in vitro and influence on the barrier integrity. Molecular nutrition & food research 20120301
Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market. Journal of agricultural and food chemistry 20111228
Effect of ergot alkaloids on contractility of bovine right ruminal artery and vein. Journal of animal science 20110901
Cytotoxicity and accumulation of ergot alkaloids in human primary cells. Toxicology 20110411
Ricinoleic acid as a marker for ergot impurities in rye and rye products. Journal of agricultural and food chemistry 20100414
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids. Journal of animal science 20100101
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue. Journal of agricultural and food chemistry 20090826
A basic tool for risk assessment: a new method for the analysis of ergot alkaloids in rye and selected rye products. Molecular nutrition & food research 20090401
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer. International journal of molecular sciences 20081201
Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081001
Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Journal of medicinal chemistry 20080612
Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement. Journal of natural products 20080601
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS. Analytical and bioanalytical chemistry 20080501
LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080401
Ergot alkaloids in rye flour determined by solid-phase cation-exchange and high-pressure liquid chromatography with fluorescence detection. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080301
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples. Journal of AOAC International 20080101
A comparative study of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in oclular normotensive and alpha-chymotrypsin-induced ocular hypertensive rabbits. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20071001
Effects of different levels of ergot in concentrates on the growing and slaughtering performance of bulls and on carry-over into edible tissue. Archives of animal nutrition 20071001
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach. Rapid communications in mass spectrometry : RCM 20070101
Quantitative determination of five ergot alkaloids in rye flour by liquid chromatography-electrospray ionisation tandem mass spectrometry. Journal of chromatography. A 20060505
Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments. Rapid communications in mass spectrometry : RCM 20060101
The influence of ergot-contaminated feed on growth and slaughtering performance, nutrient digestibility and carry over of ergot alkaloids in growing-finishing pigs. Archives of animal nutrition 20051201
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds. Journal of mass spectrometry : JMS 20051101
The ergot alkaloid gene cluster in Claviceps purpurea: extension of the cluster sequence and intra species evolution. Phytochemistry 20050601
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens. Archives of animal nutrition 20050401
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry. Journal of mass spectrometry : JMS 20041101
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. The Journal of pharmacology and experimental therapeutics 20021001
Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Molecular pharmacology 20020501
Does decreased mowing frequency enhance alkaloid production in endophytic tall fescue and perennial ryegrass? Journal of chemical ecology 20020501
The effect of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in rabbits with alpha-chymotrypsin-induced ocular hypertension. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20020401
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20020201
Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc 20010501
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