Ochratoxin A - Moligand™, ≥98% , CAS No.303-47-9

CAS: 303-47-9 Cat. No.: O102402 Summenformel: C₂₀H₁₈ClNO₆ Molekulargewicht: 403.81 Beilstein Registry Number: 8169012 EG-Nummer: 206-143-7

QUALITÄT & REINHEIT Moligand™, ≥98%

Synonyms

OCHRATOXIN A|3R14S-Ochratoxin A|Ochratoxin A-BSA conjugate from Aspergillus ochraceus|OTA|Phenylalanine - ochratoxin A|Ochratoxin A(OTA)|Antibiotic 9663|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads,FedEx DG Service

Übersicht

Ochratoxin A is a mycotoxin isolated from the Aspergillus ochraceus mold, a common fungal presence on moldy food. Ochratoxin A demonstrates nephrotoxicity and teratogenesis in animals, and shows inhibition of bacterial, yeast, and liver FARSL (phenylalanyl-tRNA synthetases) competitive with phenylalanine. As these activities are partially attenuated by phenylalanine, Ochratoxin A is suggested to produce its effects through interacting with proteins that recognize phenylalanine as a substrate, and has been demonstrated to inhibit PAH (phenylalanine hydroxylase). Derivatives of Ochratoxin A with other amino acid moieties substituted for the phenylalanine-mimic portion of the molecule demonstrate inhibition of the aminoacyl tRNA synthetases respective to those amino acids. Ochratoxin A is described to enhance lipid peroxidation and also present DNA single strand breaks, both suggesting oxidative damage as a partial mediator of Ochratoxin A cellular effects, and EPR spectroscopy with a spin trap agent identified the production of hydroxyl radicals by Ochratoxin A in the presence of NADPH. The nephrotoxic effects of Ochratoxin A are shown to be prevented by SOD (superoxide dismutase) and catalase, further indicating oxidative damage as the mediator of Ochratoxin A toxicity. Ochratoxin A is also demonstrated to increase ATP-dependent Ca2+ pump activity in renal cortex endoplasmic reticulum.Ochratoxin A is one of the mycotoxins typically produced by the species of Aspergillus genus. It is a commonly found secondary metabolite in cereals, coffee, grape must, wine, beer, etc.
A nephrotoxic mycotoxin inhibitor of phenylalanyl-tRNA synthetases.

Spezifikationen

Synonyme

OCHRATOXIN A | 3R14S-Ochratoxin A | Ochratoxin A-BSA conjugate from Aspergillus ochraceus | OTA | Phenylalanine - ochratoxin A | Ochratoxin A(OTA) | Antibiotic 9663 | (-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine

Spezifikationen & Reinheit

Moligand™, ≥98%

Biochemische und physiologische Mechanismen

Mycotoxin that increases activity of the endoplasmic reticulum ATP-dependent calcium pump. Induces JNK activation and apoptosis in MDCK-C7 cells at nanomolar concentrations. Stimulates lipid peroxidation.

Storage

Protected from light,Store at -20°C

Verschickt in

Ice chest + Ice pads,FedEx DG Service

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Moligand™

Reinheit

≥98%

Namen und Kennungen

Pubchem Sid

488189794

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488189794

Kanonisches Lächeln

CC1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)NC(CC3=CC=CC=C3)C(=O)O)Cl

IUPAC Name

(2S)-2-[[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid

InChIKey

RWQKHEORZBHNRI-BMIGLBTASA-N

INCHI

1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1

Isomere SMILES

C[C@@H]1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)Cl

WGK Deutschland

3

UN-Nummer

2811

Verpackungsgruppe

I

Molekulargewicht

403.81

Beilstein

8169012

Reaxy-Rn

1442621

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1442621&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Ochratoxins and related substances

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Ochratoxins and related substances
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Ochratoxins and related substances
• Alternative Parents: Phenylalanine and derivatives N-acyl-alpha amino acids Phenylpropanoic acids Salicylic acid and derivatives 2-benzopyrans Amphetamines and derivatives Aryl chlorides Dicarboxylic acids and derivatives Vinylogous acids Secondary carboxylic acid amides Carboxylic acid esters Lactones Oxacyclic compounds Carboxylic acids Organopnictogen compounds Organochlorides Carbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Ochratoxin-skeleton - Phenylalanine or derivatives - N-acyl-alpha amino acid or derivatives - N-acyl-alpha-amino acid - 3-phenylpropanoic-acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Salicylic acid or derivatives - 2-benzopyran - Isochromane - Benzopyran - Aryl halide - Benzenoid - Aryl chloride - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Vinylogous acid - Carboxamide group - Carboxylic acid ester - Secondary carboxylic acid amide - Lactone - Carboxylic acid - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as ochratoxins and related substances. These are a group of chemically related metabolites containing a 3,4-dihydro-3-methylisocoumarin moiety linked through a carboxyl group to L-beta-phenylalanine by a secondary amine bond.
• External Descriptors: Mycotoxins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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GLA Tclin Alpha-galactosidase A (5444 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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HepG2 (196354 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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SLC22A8 Tclin Solute carrier family 22 member 8 (241 Activities)

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SLC22A7 Tbio Solute carrier family 22 member 7 (39 Activities)

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SLC22A11 Tclin Solute carrier family 22 member 11 (82 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Slc22a20 Solute carrier family 22 member 20 (86 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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BCHE Cholinesterase (8742 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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FTL Ferritin light chain (43324 Activities)

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mshC L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase (54 Activities)

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Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)

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Slc22a19 Putative organic anion transporter 5 (5 Activities)

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: Solvent:ethanol, Max Conc. mg/mL: 20.19, Max Conc. mM: 50; Solvent:DMSO, Max Conc. mg/mL: 40.38, Max Conc. mM: 100
• Empfindlichkeit: Moisture sensitive；Light sensitive
• Flammpunkt (°C): -11°C
• Molekulargewicht: 403.800 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 403.082 Da
• Monoisotopic Mass: 403.082 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 608.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1