Ochratoxin C
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Basic Info
| Common Name | Ochratoxin C(F04881) |
| 2D Structure | |
| Description | Ochratoxin C is a metabolite of Aspergillus ochraceus Ochratoxin C belongs to the family of Ochratoxins and related substances. These are compounds containing the ochratoxin skeleton, which is structurally characterized by the presence of a 3-phenylpropanoic acid N-linked to a 8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxamide moiety[1]. (Reference: [1] http://www.inchem.org/documents/ehc/ehc/ehc105.htm). |
| FRCD ID | F04881 |
| CAS Number | 4865-85-4 |
| PubChem CID | 617474 |
| Formula | C22H22ClNO6 |
| IUPAC Name | ethyl 2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoate |
| InChI Key | BPZZWRPHVVDAPT-UHFFFAOYSA-N |
| InChI | InChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26) |
| Canonical SMILES | CCOC(=O)C(CC1=CC=CC=C1)NC(=O)C2=CC(=C3CC(OC(=O)C3=C2O)C)Cl |
| Isomeric SMILES | CCOC(=O)C(CC1=CC=CC=C1)NC(=O)C2=CC(=C3CC(OC(=O)C3=C2O)C)Cl |
| Wikipedia | Ochratoxin C |
| Synonyms |
2-[(3,4-Dihydro-1-oxo-3-methyl-5-chloro-8-hydroxy-1H-2-benzopyran-7-yl)carbonylamino]-3-phenylpropanoic acid ethyl ester
AC1LDF9C
Ochratoxin A ethyl ester
SCHEMBL455356
DTXSID40347047
18496-58-7
ethyl 2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido]-3-phenylpropanoate
ethyl 2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoate
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Ochratoxins and related substances |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ochratoxins and related substances |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Ochratoxin-skeleton - Phenylalanine or derivatives - Alpha-amino acid ester - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Isochromane - Benzopyran - Salicylic acid or derivatives - Amphetamine or derivatives - 2-benzopyran - Fatty acid ester - Benzenoid - Monocyclic benzene moiety - Fatty acyl - Dicarboxylic acid or derivatives - Aryl halide - Aryl chloride - Vinylogous acid - Carboxylic acid ester - Lactone - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Organic nitrogen compound - Organohalogen compound - Carbonyl group - Organochloride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 431.869 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Complexity | 637 |
| Monoisotopic Mass | 431.114 |
| Exact Mass | 431.114 |
| XLogP | 5.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 30 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.8688 |
| Human Intestinal Absorption | HIA+ | 0.8650 |
| Caco-2 Permeability | Caco2- | 0.6048 |
| P-glycoprotein Substrate | Substrate | 0.6277 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8222 |
| Non-inhibitor | 0.8192 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9079 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4887 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7488 |
| CYP450 2D6 Substrate | Non-substrate | 0.8254 |
| CYP450 3A4 Substrate | Substrate | 0.6457 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6263 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6149 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8716 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5624 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5261 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6938 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9657 |
| Non-inhibitor | 0.8396 | |
| AMES Toxicity | Non AMES toxic | 0.7139 |
| Carcinogens | Non-carcinogens | 0.8718 |
| Fish Toxicity | High FHMT | 0.9370 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9986 |
| Honey Bee Toxicity | Low HBT | 0.7068 |
| Biodegradation | Not ready biodegradable | 0.9839 |
| Acute Oral Toxicity | III | 0.4700 |
| Carcinogenicity (Three-class) | Danger | 0.4507 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3558 | LogS |
| Caco-2 Permeability | 0.3920 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.2933 | LD50, mol/kg |
| Fish Toxicity | 0.7047 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7962 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Broad-specificity photoelectrochemical immunoassay for the simultaneous detection of ochratoxin A, ochratoxin B and ochratoxin C. | Biosens Bioelectron | 2018 May 30 | 29428592 |
| Broad-Specificity Immunoassay for Simultaneous Detection of Ochratoxins A, B, and C in Millet and Maize. | J Agric Food Chem | 2017 Jun 14 | 28535353 |
| Nuclease-aided target recycling signal amplification strategy for ochratoxin A monitoring. | Biosens Bioelectron | 2017 Jan 15 | 27542086 |
| Comparative Ochratoxin Toxicity: A Review of the Available Data. | Toxins (Basel) | 2015 Oct 22 | 26506387 |
| Development of a sensitive enzyme-linked immunosorbent assay for the determination of ochratoxin A. | J Agric Food Chem | 2005 Aug 24 | 16104825 |
| Ochratoxin A and some of its derivatives modulate radical formation of porcine blood monocytes and granulocytes. | Toxicology | 2004 Jul 1 | 15147798 |
| Ochratoxin A in table wine and grape-juice: occurrence and risk assessment. | Food Addit Contam | 1996 Aug-Sep | 8871123 |
| Production of ochratoxins in different cereal products by Aspergillus ochraceus. | Appl Microbiol | 1971 Jun | 5564676 |
Targets
- General Function:
- Phosphoenolpyruvate carboxykinase (gtp) activity
- Specific Function:
- Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle.
- Gene Name:
- PCK1
- Uniprot ID:
- P35558
- Molecular Weight:
- 69193.975 Da
- Mechanism of Action:
- Ochratoxin A, a metabolite of Ochratoxin C,is an inhibitor of renal phosphoenolpyruvate carboxykinase.
References
- Meisner H, Meisner P: Ochratoxin A, an in vivo inhibitor of renal phosphoenolpyruvate carboxykinase. Arch Biochem Biophys. 1981 Apr 15;208(1):146-53. [7259174 ]
- General Function:
- Ubiquinone binding
- Specific Function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
- Gene Name:
- SDHD
- Uniprot ID:
- O14521
- Molecular Weight:
- 17042.82 Da
- Mechanism of Action:
- Ochratoxin A, a metabolite of Ochratoxin C,is an uncompetitive inhibitor of succinate dehydrogenase.
References
- Wei YH, Lu CY, Lin TN, Wei RD: Effect of ochratoxin A on rat liver mitochondrial respiration and oxidative phosphorylation. Toxicology. 1985 Aug;36(2-3):119-30. [2996181 ]
- General Function:
- Ubiquinone binding
- Specific Function:
- Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
- Gene Name:
- SDHB
- Uniprot ID:
- P21912
- Molecular Weight:
- 31629.365 Da
- Mechanism of Action:
- Ochratoxin A, a metabolite of Ochratoxin C,is an uncompetitive inhibitor of succinate dehydrogenase.
References
- Wei YH, Lu CY, Lin TN, Wei RD: Effect of ochratoxin A on rat liver mitochondrial respiration and oxidative phosphorylation. Toxicology. 1985 Aug;36(2-3):119-30. [2996181 ]