NP-MRD: Showing NP-Card for Ochratoxin A (NP0045356)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:31 UTC

Updated at

2022-03-17 19:18:31 UTC

NP-MRD ID

NP0045356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ochratoxin A

Description

Ochratoxin A, also known as OTA or antibiotic 9663, 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. 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. Ochratoxin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ochratoxin A has been detected, but not quantified in, a few different foods, such as barley, cereals and cereal products, and common wheats. This could make ochratoxin a a potential biomarker for the consumption of these foods. Ochratoxin A toxicity has large species- and sex-specific differences. Ochratoxin A, a toxin produced by Aspergillus ochraceus and Penicillium verrucosum, is one of the most abundant food-contaminating mycotoxins in the world. Production by Aspergillus melleus, Aspergillus sulphureus and Penicillium viridicatum. Potential contaminant of foodstuffs, especially cereals. Ochratoxin A is found in Apis cerana, Aspergillus melleus, Aspergillus ochraceus, Aspergillus spp., Aspergillus sulphureus, Penicillium nordicum, Penicillium spp., Penicillium verrucosum and Penicillium viridicatum. Ochratoxin A was first documented in 2001 (PMID: 11513689). The toxin has been found in the tissues and organs of animals, including human blood and breast milk (PMID: 11899122) (PMID: 15056805) (PMID: 16022500) (PMID: 16097797) (PMID: 16293235) (PMID: 16332622).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241220292D          

 28 30  0  0  0  0            999 V2000
    3.5720   -0.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8569   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8569    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.6776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720    0.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720   -1.5026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8569   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -2.7400    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  2  0  0  0  0
  2 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 28  1  6  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    6.3799    1.1581    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3638   -0.3403    0.2358 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4989   -0.9383   -0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0683   -0.6633   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035   -0.6257   -1.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -0.9025   -3.2699 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8582   -0.3700   -1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512   -0.1479   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0668    0.1209    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    0.3212    1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077    0.1717   -1.0153 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068    0.4420   -0.7829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0344   -0.6839   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4503   -0.5203    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -0.9107   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7689   -0.7879   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2124   -0.2730    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2775    0.1265    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240   -0.0022    1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285    1.7175   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    2.4243    0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    2.1899    0.2513 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.1884    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.0065    2.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -0.4493    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5287   -0.4916    1.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -0.2981    2.9414 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726   -0.7552    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7878    1.5621    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392    1.5529    0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0196    1.5540   -0.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3960   -0.6956    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443   -0.5695   -1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -2.0493   -0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.3469   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    0.0087   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712    0.5148   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -0.7908    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -1.6732   -0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1383   -1.3264   -1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107   -1.1052   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2799   -0.1771    0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6660    0.5302    2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2353    0.3274    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    3.1548    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738    0.1993    2.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 23  1  0
 23 24  1  0
 23  8  2  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 22  1  0
 20 21  2  0
 28  2  1  0
 19 14  1  0
  5  4  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
 24 46  1  0
  7 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 22 45  1  0
M  END


  Mrv0541 02241220292D          

 28 30  0  0  0  0            999 V2000
    3.5720   -0.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8569   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8569    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.6776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720    0.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720   -1.5026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8569   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -2.7400    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  2  0  0  0  0
  2 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0045356

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C20H18ClNO6

> <MOLECULAR_WEIGHT>
403.813

> <EXACT_MASS>
403.08226502

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.12124291419772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
4.611055944

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.945288735184751

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1733449085037986

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0440110847627158

> <JCHEM_POLAR_SURFACE_AREA>
112.93

> <JCHEM_REFRACTIVITY>
101.76999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ochratoxin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       6.668  -1.265   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.333  -0.495   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.333   1.045   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -1.335  -1.265   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.667  -0.495   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -1.265   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.336  -0.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.336   1.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   1.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   1.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -0.495   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -1.265   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001   1.815   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   1.045   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.335   1.815   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.805   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.333  -3.575   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.805   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -1.265   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -0.495   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   1.045   0.000  0.00  0.00           O+0
HETATM   22 Cl   UNK     0       2.667  -5.115   0.000  0.00  0.00          Cl+0
HETATM   23  C   UNK     0       2.667  -3.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -2.805   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -1.265   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000  -0.495   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.000   1.045   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.001  -3.575   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2                                                            
CONECT    4    5   26                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11                                                       
CONECT   13   14                                                            
CONECT   14    5   13   15                                                  
CONECT   15   14                                                            
CONECT   16    1   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19    2   18   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   18   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24   26                                                  
CONECT   26    4   25   27                                                  
CONECT   27   26                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acid	ChEBI
(R)-N-((5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)phenylalanine	ChEBI
N-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine	ChEBI
N-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine	ChEBI
OTA	ChEBI
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoate	Generator
Antibiotic 9663	HMDB
N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]phenylalanine, 9ci	HMDB
Ochratoxin a-bsa conjugate from aspergillus ochraceus	HMDB
Phenylalanine - ochratoxin a	HMDB

Chemical Formula

C₂₀H₁₈ClNO₆

Average Mass

403.8130 Da

Monoisotopic Mass

403.08227 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Aspergillus melleus	Fungi	KNApSAcK
Aspergillus ochraceus	Fungi	KNApSAcK
Aspergillus spp.	Fungi	KNApSAcK
Aspergillus sulphureus	Fungi	KNApSAcK
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Penicillium nordicum	LOTUS Database	35616633
Penicillium spp.	Fungi	KNApSAcK
Penicillium verrucosum	LOTUS Database	35616633
Penicillium viridicatum	Fungi	KNApSAcK
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:7719 )
organochlorine compound (CHEBI:7719 )
phenylalanine derivative (CHEBI:7719 )
N-acyl-L-phenylalanine (CHEBI:7719 )
isochromanes (CHEBI:7719 )
Mycotoxins (C09955 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.18	ALOGPS
logP	4.61	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.93 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.77 m³·mol⁻¹	ChemAxon
Polarizability	40.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029399

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ochratoxin_A

METLIN ID

Not Available

PubChem Compound

442530

PDB ID

Not Available

ChEBI ID

7719

Good Scents ID

Not Available

References

General References

Castellari M, Versari A, Fabiani A, Parpinello GP, Galassi S: Removal of ochratoxin A in red wines by means of adsorption treatments with commercial fining agents. J Agric Food Chem. 2001 Aug;49(8):3917-21. doi: 10.1021/jf010137o. [PubMed:11513689 ]
Schwartz GG: Hypothesis: does ochratoxin A cause testicular cancer? Cancer Causes Control. 2002 Feb;13(1):91-100. doi: 10.1023/a:1013973715289. [PubMed:11899122 ]
Assaf H, Azouri H, Pallardy M: Ochratoxin A induces apoptosis in human lymphocytes through down regulation of Bcl-xL. Toxicol Sci. 2004 Jun;79(2):335-44. doi: 10.1093/toxsci/kfh123. Epub 2004 Mar 31. [PubMed:15056805 ]
Turesky RJ: Perspective: ochratoxin A is not a genotoxic carcinogen. Chem Res Toxicol. 2005 Jul;18(7):1082-90. doi: 10.1021/tx050076e. [PubMed:16022500 ]
Mally A, Volkel W, Amberg A, Kurz M, Wanek P, Eder E, Hard G, Dekant W: Functional, biochemical, and pathological effects of repeated oral administration of ochratoxin A to rats. Chem Res Toxicol. 2005 Aug;18(8):1242-52. doi: 10.1021/tx049651p. [PubMed:16097797 ]
Ringot D, Chango A, Schneider YJ, Larondelle Y: Toxicokinetics and toxicodynamics of ochratoxin A, an update. Chem Biol Interact. 2006 Jan 5;159(1):18-46. doi: 10.1016/j.cbi.2005.10.106. Epub 2005 Nov 15. [PubMed:16293235 ]
Fuchs R, Peraica M: Ochratoxin A in human kidney diseases. Food Addit Contam. 2005;22 Suppl 1:53-7. doi: 10.1080/02652030500309368. [PubMed:16332622 ]
Scott PM: Biomarkers of human exposure to ochratoxin A. Food Addit Contam. 2005;22 Suppl 1:99-107. doi: 10.1080/02652030500410315. [PubMed:16332628 ]
Patil RD, Dwivedi P, Sharma AK: Critical period and minimum single oral dose of ochratoxin A for inducing developmental toxicity in pregnant Wistar rats. Reprod Toxicol. 2006 Nov;22(4):679-87. doi: 10.1016/j.reprotox.2006.04.022. Epub 2006 Jun 14. [PubMed:16781114 ]
Pfohl-Leszkowicz A, Manderville RA: Ochratoxin A: An overview on toxicity and carcinogenicity in animals and humans. Mol Nutr Food Res. 2007 Jan;51(1):61-99. doi: 10.1002/mnfr.200600137. [PubMed:17195275 ]
Schwerdt G, Holzinger H, Sauvant C, Konigs M, Humpf HU, Gekle M: Long-term effects of ochratoxin A on fibrosis and cell death in human proximal tubule or fibroblast cells in primary culture. Toxicology. 2007 Mar 22;232(1-2):57-67. doi: 10.1016/j.tox.2006.12.008. Epub 2006 Dec 15. [PubMed:17218050 ]
Chung SW, Kwong KP: Determination of ochratoxin A at parts-per-trillion levels in cereal products by immunoaffinity column cleanup and high-performance liquid chromatography/mass spectrometry. J AOAC Int. 2007 May-Jun;90(3):773-7. [PubMed:17580629 ]
Bouslimi A, Bouaziz C, Ayed-Boussema I, Hassen W, Bacha H: Individual and combined effects of ochratoxin A and citrinin on viability and DNA fragmentation in cultured Vero cells and on chromosome aberrations in mice bone marrow cells. Toxicology. 2008 Sep 29;251(1-3):1-7. doi: 10.1016/j.tox.2008.06.008. Epub 2008 Jun 28. [PubMed:18638518 ]
Amezqueta S, Gonzalez-Penas E, Lizarraga T, Murillo-Arbizu M, Lopez de Cerain A: A simple chemical method reduces ochratoxin A in contaminated cocoa shells. J Food Prot. 2008 Jul;71(7):1422-6. doi: 10.4315/0362-028x-71.7.1422. [PubMed:18680942 ]
Cramer B, Harrer H, Nakamura K, Uemura D, Humpf HU: Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers. Bioorg Med Chem. 2010 Jan 1;18(1):343-7. doi: 10.1016/j.bmc.2009.10.050. Epub 2009 Oct 30. [PubMed:19919898 ]

Showing NP-Card for Ochratoxin A (NP0045356)

MOL for NP0045356 (Ochratoxin A)

3D MOL for NP0045356 (Ochratoxin A)

3D SDF for NP0045356 (Ochratoxin A)

3D-SDF for NP0045356 (Ochratoxin A)

PDB for NP0045356 (Ochratoxin A)

3D PDB for NP0045356 (Ochratoxin A)

SMILES for NP0045356 (Ochratoxin A)

INCHI for NP0045356 (Ochratoxin A)

Structure for NP0045356 (Ochratoxin A)

3D Structure for NP0045356 (Ochratoxin A)