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

CAS: 303-47-9 Cat. No.: O102402 Formule: C₂₀H₁₈ClNO₆ Poids moléculaire: 403.81 Beilstein Registry Number: 8169012 Numéro CE: 206-143-7

QUALITÉ & PURETÉ 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

Vue d’ensemble

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.

Spécifications

Synonymes

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

Spécifications et pureté

Moligand™, ≥98%

Mécanismes biochimiques et physiologiques

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.

Conditions de stockage de stockage

Protected from light,Store at -20°C

Expédié en

Ice chest + Ice pads,FedEx DG Service

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Pureté

≥98%

Noms et identifiants

Pubchem Sid

488189794

Pubchem Sid Url

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

Sourires canoniques

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

Isomères 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 Allemagne

3

Numéro ONU

2811

Groupe d'emballage

I

Poids moléculaire

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
    • Classe Ochratoxins and related substances

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: 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
• Description: 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

Cibles associées (humaines)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: THRB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLA Tclin Alpha-galactosidase A (5444 Activities)

Discover Target: GLA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

Discover Target: GBA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

Discover Target: GAA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: NFKB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

Discover Target: TP53

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: ABCC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: HPGD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: SLC22A8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: SLC22A7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: SLC22A11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cibles associées (non humaines)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

Discover Target: Ppard

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a20 Solute carrier family 22 member 20 (86 Activities)

Discover Target: Slc22a20

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a6 Solute carrier family 22 member 6 (141 Activities)

Discover Target: Slc22a6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Impa1 Inositol monophosphatase 1 (16203 Activities)

Discover Target: Impa1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: mshC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: Slco1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a19 Putative organic anion transporter 5 (5 Activities)

Discover Target: Slc22a19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mécanismes d'action

Propriétés chimiques et physiques

• Solubilité: Solvent:ethanol, Max Conc. mg/mL: 20.19, Max Conc. mM: 50; Solvent:DMSO, Max Conc. mg/mL: 40.38, Max Conc. mM: 100
• Sensibilité: Moisture sensitive；Light sensitive
• Point d'éclair (°C): -11°C
• Poids moléculaire: 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