T3DB: Ochratoxin C

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2009-11-13 22:52:25 UTC

Update Date

2014-12-24 20:26:13 UTC

Accession Number

T3D3607

Identification

Common Name

Ochratoxin C

Class

Small Molecule

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).

Compound Type

Amide
Amine
Ester
Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound
Organochloride

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Ochratoxin a ethyl ester

Chemical Formula

C₂₂H₂₂ClNO₆

Average Molecular Mass

431.866 g/mol

Monoisotopic Mass

431.114 g/mol

CAS Registry Number

4865-85-4

IUPAC Name

5-chloro-N-(1-ethoxy-1-oxo-3-phenylpropan-2-yl)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboximidic acid

Traditional Name

5-chloro-N-(1-ethoxy-1-oxo-3-phenylpropan-2-yl)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-carboximidic acid

SMILES

CCOC(=O)C(CC1=CC=CC=C1)N=C(O)C1=CC(Cl)=C2CC(C)OC(=O)C2=C1O

InChI Identifier

InChI=1/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)

InChI Key

InChIKey=BPZZWRPHVVDAPT-UHFFFAOYNA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

Hexose monosaccharide
N-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
Aralkylamine
Monosaccharide
Oxane
Azole
Heteroaromatic compound
Isoxazole
Vinylogous amide
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Amine
Organopnictogen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxide
Primary aliphatic amine
Primary amine
Organonitrogen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.96	ALOGPS
logP	5.93	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.42 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.81 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4019000000-d2a641a855118404e3bc	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03fu-9002260000-31b2f835982ccd442d9f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-4212900000-efe849f14e9d887fdfa1	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-4397400000-e2938a4d4ece4b5ee369	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9210000000-46647db7246af80a6e10	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2019500000-0e6b84dd14ef1152c403	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-6469400000-2b606454b44f5e5551c0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9111000000-78fb701981189e5cacd6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-7ea3cfffa1f605d198df	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f7o-4935800000-9f550c61aeec7cbd7cf4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-4491000000-f6cb7f8400d2bc6255b5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0004900000-4bdf05cff8a50f221350	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5l-2593300000-926aecf8ff2fc365bdca	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-8950000000-00fa22804f8981975e62	2021-09-22	View Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (3)

Mechanism of Toxicity

Ochratoxin A, a metabolite of Ochratoxin C, has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage. The nephrotoxin ochratoxin A (OTA) causes a reduction of glomerular filtration rate (GFR) and of para-aminohippuric acid (PAH) clearance. It is a nephrotoxin which blocks plasma membrane anion conductance in Madin-Darby canine kidney (MDCK) cells. (4)

Metabolism

It is concluded that ochratoxin C is readily converted to ochratoxin A after both oral and intravenous administration. (1)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Human exposure occurs mainly through consumption of improperly stored food products, particularly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. (8)

Minimum Risk Level

Not Available

Health Effects

Ochratoxin exposure has been associated with acute tubular necrosis and Balkan endemic nephropathy. Ochratoxin A has been shown to be nephrotoxic; might delay sexual maturation. (5)

Symptoms

Might cause respiratory irritation. (5)

Treatment

Care is symptomatic and supportive. (5)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB29400

PubChem Compound ID

617474

ChEMBL ID

Not Available

ChemSpider ID

536626

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Ochratoxin

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Fuchs R, Hult K, Peraica M, Radic B, Plestina R: Conversion of ochratoxin C into ochratoxin A in vivo. Appl Environ Microbiol. 1984 Jul;48(1):41-2. [6476830 ]
Hietanen E, Bartsch H, Bereziat JC, Castegnaro M, Michelon J: Characterization of the cytochrome P450 isozyme that metabolizes ochratoxin A, using metabolic inducers, inhibitors and antibodies. IARC Sci Publ. 1991;(115):297-304. [1820345 ]
Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Gekle M, Silbernagl S: Mechanism of ochratoxin A-induced reduction of glomerular filtration rate in rats. J Pharmacol Exp Ther. 1993 Oct;267(1):316-21. [8229758 ]
Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [15509185 ]
Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Wikipedia. Ochratoxin A. Last Updated 26 February 2010. [Link]
Wikipedia. Ochratoxin. Last Updated 29 March 2010. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]

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

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 ]

Target Details

2. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial

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

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 ]

Target Details

3. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial

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

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 ]

Ochratoxin C (T3D3607)

Structure for T3D3607: Ochratoxin C

Targets

References

References

References