| Common Name |
Ochratoxin A
| Description |
Ochratoxin A is found in barley. Mycotoxin. Ochratoxin A is produced by Aspergillus melleus, Aspergillus sliphureus and Penicillium viridicatum.Potential contaminant of foodstuffs, especially cereals. Ochratoxin A is found in stored grain products in UK (1997).Ochratoxin A, a toxin produced by Aspergillus ochraceus and Penicillium verrucosum, is one of the most abundant food-contaminating mycotoxins in the world. Human exposure occurs mainly through consumption of improperly stored food products, particliarly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. The toxin has been found in the tissues and organs of animals, including human blood and breast milk. Ochratoxin A toxicity has large species- and sex-specific differences.Ochratoxin a 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).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29399 (Ochratoxin A)
| Synonyms |
| Value |
Source |
(R)-N-((5-chloro-3,4-dihydro-8-Hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)phenylalanineChEBI
Antibiotic 9663HMDB
N-[(5-chloro-3,4-dihydro-8-Hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]phenylalanine, 9ciHMDB
Ochratoxin a-bsa conjugate from aspergillus ochraceusHMDB
OTAHMDB
Phenylalanine – ochratoxin aHMDB
| Chemical Formlia |
C20H18ClNO6
| Average Molecliar Weight |
403.813
| Monoisotopic Molecliar Weight |
403.08226502
| IUPAC Name |
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid
| Traditional Name |
ochratoxin A
| CAS Registry Number |
303-47-9
| SMILES |
C[C@@H]1CC2=C(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
| InChI Identifier |
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
| InChI Key |
RWQKHEORZBHNRI-BMIGLBTASA-N
| Chemical Taxonomy |
| 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.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Ochratoxins and related substances
| Sub Class |
Not Available
| Direct Parent |
Ochratoxins and related substances
| Alternative Parents |
N-acyl-alpha amino acids
Hippuric acids
Phenylpropanoic acids
Salicylic acid and derivatives
Amphetamines and derivatives
3-halobenzoic acids and derivatives
2-benzopyrans
Halophenols
Benzoyl derivatives
Chlorobenzenes
Amino fatty acids
Dicarboxylic acids and derivatives
Aryl chlorides
Vinylogous acids
Secondary carboxylic acid amides
Lactones
Carboxylic acid esters
Oxacyclic compounds
Carboxylic acids
Organonitrogen compounds
Organochlorides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Ochratoxin-skeleton
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
3-phenylpropanoic-acid
2-benzopyran
3-halobenzoic acid or derivatives
Salicylic acid or derivatives
Isochromane
Benzopyran
Amphetamine or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Benzamide
4-halophenol
Benzoyl
Chlorobenzene
Amino fatty acid
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Vinylogous acid
Secondary carboxylic acid amide
Lactone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
organochlorine compound (CHEBI:7719 )
monocarboxylic acid amide (CHEBI:7719 )
N-acyl-L-phenylalanine (CHEBI:7719 )
phenylalanine derivative (CHEBI:7719 )
isochromanes (CHEBI:7719 )
Mycotoxins (C09955 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Toxic Substance
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point169 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.74Not Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.023 mg/mLALOGPS
logP3.18ALOGPS
logP4.61ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.93 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.77 m3·mol-1ChemAxon
Polarizability40.12 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000488
| KNApSAcK ID |
C00003008
| Chemspider ID |
390954
| KEGG Compound ID |
C09955
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Ochratoxin_A
| NuGOwiki Link |
HMDB29399
| Metagene Link |
HMDB29399
| METLIN ID |
Not Available
| PubChem Compound |
442530
| PDB ID |
Not Available
| ChEBI ID |
7719
Product: Lasmiditan (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 17649988
