Compounds > ochratoxin c
Page last updated: 2024-11-05

ochratoxin c

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Ochratoxin C (OTC) is a mycotoxin produced by various species of Aspergillus and Penicillium fungi. It is a structurally related compound to ochratoxin A (OTA), a known nephrotoxin and carcinogen, but with a different substitution on the isocoumarin moiety. While OTC has been reported to be less toxic than OTA, it still exhibits some biological activity. Limited research suggests potential cytotoxic effects and interference with cellular processes, but further investigation is needed to fully understand its toxicological significance. Its presence in food and feed can be a concern, particularly considering the potential for synergistic effects with other mycotoxins. OTC is studied to assess its potential risk to human and animal health and to develop strategies for its mitigation. The research aims to understand its biosynthesis, occurrence in food, and the mechanisms of its toxicity. This knowledge is crucial for implementing effective control measures and ensuring food safety.'

ochratoxin C: converted into ochratoxin A in vivo; RN given refers to (R)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ochratoxin C : A phenylalanine derivative that is the ethyl ester of ochratoxin A. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID20997
CHEBI ID141525
SCHEMBL ID455355
MeSH IDM0125606

Synonyms (27)

Synonym
ochratoxin c
ethyl (2s)-2-[[(3r)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoate
ethyl n-{[(3r)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1h-isochromen-7-yl]carbonyl}-l-phenylalaninate
CHEBI:141525
4865-85-4
ochratoxin a ethyl ester
ethyl (2s)-2-{[(3r)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1h-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoate
ethyl n-[(3r)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1h-2-benzopyran-7-carbonyl]-l-phenylalaninate
unii-0dy21hw450
0dy21hw450 ,
alanine, n-((5-chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenyl-, ethyl ester, l-
hsdb 3439
l-phenylalanine, n-((5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1h-2-benzopyran-7-yl)carbonyl)-, ethyl ester, (r)-
l-phenylalanine, n-(((3r)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1h-2-benzopyran-7-yl)carbonyl)-, ethyl ester
ochratoxin c [mi]
ochratoxin c [hsdb]
SCHEMBL455355
ethyl 2-([(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1h-isochromen-7-yl)carbonyl]amino)-3-phenylpropanoate #
BPZZWRPHVVDAPT-PXAZEXFGSA-N
l-phenylalanine, n-[(5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1h-2-benzopyran-7-yl)carbonyl]-, ethyl ester, (r)-
ethyl ((r)-5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carbonyl)-l-phenylalaninate
Q15633527
DTXSID00964097
CS-0093077
HY-125699
l-phenylalanine, n-[[(3r)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1h-2-benzopyran-7-yl]carbonyl]-, ethyl ester
AKOS040753349

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" OTA is regarded as the most toxic family member, however, other ochratoxins or their metabolites and, in particular, ochratoxin mixtures or combinations with other mycotoxins may represent serious threats to human and animal health."( Comparative Ochratoxin Toxicity: A Review of the Available Data.
Bingle, LE; Heussner, AH, 2015)		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
Aspergillus metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
Penicillium metaboliteAny fungal metabolite produced during a metabolic reaction in Penicillium.
mycotoxinPoisonous substance produced by fungi.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
alpha-amino acid esterThe amino acid ester derivative obtained the formal condensation of an alpha-amino acid with an alcohol.
phenylalanine derivativeAn amino acid derivative resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of phenylalanine by a heteroatom. The definition normally excludes peptides containing phenylalanine residues.
isochromanes
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's4 (50.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.47

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.47 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
patulin
Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.		7.2510furopyran;
gamma-lactone;
lactol		antimicrobial agent;
Aspergillus metabolite;
carcinogenic agent;
mutagen;
mycotoxin;
Penicillium metabolite
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9710amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
ochratoxin b
ochratoxin B: structure given in first source. ochratoxin B : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 mug/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations.		9.4560isochromanes;
monocarboxylic acid;
N-acyl-L-phenylalanine;
phenylalanine derivative		Aspergillus metabolite;
calcium channel blocker;
mycotoxin;
Penicillium metabolite
deoxynivalenol
deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.		7.2510cyclic ketone;
enone;
primary alcohol;
secondary alpha-hydroxy ketone;
trichothecene;
triol		mycotoxin
ochratoxin a
ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.		9.3960isochromanes;
monocarboxylic acid amide;
N-acyl-L-phenylalanine;
organochlorine compound;
phenylalanine derivative		Aspergillus metabolite;
calcium channel blocker;
carcinogenic agent;
mycotoxin;
nephrotoxin;
Penicillium metabolite;
teratogenic agent
t-2 toxin
T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.		7.2510
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.1510