NP-MRD: Showing NP-Card for 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid (NP0173623)

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Record Information

Version

2.0

Created at

2022-09-03 10:47:24 UTC

Updated at

2022-09-03 10:47:24 UTC

NP-MRD ID

NP0173623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

Description

Ochratoxin A 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. Ochratoxin A has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage. Ochratoxin A is cleaved into phenylalanine and a less toxic iso-coumarin derivative (ochratoxin alpha) by the microbial flora of the colon, and by carboxypeptidase A and alpha-chymotrypsim. Ochratoxin A is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyochratoxin A is the main hepatic metabolite and its formation appears to be via a polymorphic-like debrisoquine 4-hydroxylation. Ochratoxin A has been shown to be nephrotoxic and might delay sexual maturation. Ochratoxin A is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. It is a nephrotoxin which blocks plasma membrane anion conductance in Madin-Darby canine kidney (MDCK) cells. It can cause immunosuppression and immunotoxicity in animals. It's immunosuppressant activity in animals may include depressed antibody responses, reduced size of immune organs (such as the thymus, spleen, and lymph nodes), changes in immune cell number and function, and altered cytokine production. 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid is found in Aspergillus melleus and Aspergillus ochraceus. The nephrotoxin ochratoxin A (OTA) causes a reduction of glomerular filtration rate (GFR) and of para-aminohippuric acid (PAH) clearance.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09061400392D          

 28 30  0  0  0  0            999 V2000
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  4  0  0  0
 22 18  2  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 27 20  2  0  0  0  0
 28 10  1  0  0  0  0
 28 20  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    6.4532   -0.1692   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3009    0.3150    0.7017 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2688    1.3917    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8865    0.8560    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8657    1.6914    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862    3.3249   -0.2805 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5832    1.2220    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -0.0489    0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1236   -0.5139    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134   -1.8051    0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103    0.3138   -0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3858   -0.1683   -0.1590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0809    0.7616   -1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    0.3439   -1.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8322   -0.6099   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1161   -1.0490   -2.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1312   -0.5139   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    0.4340   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237    0.8600   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739   -0.1272    1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -0.5464    1.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    0.3798    2.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2378   -0.9245    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8562   -2.1910    1.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272   -0.4377    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126   -1.2741    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406   -2.4534    1.8576 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -0.7538    1.5535 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067   -1.1373   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4565   -0.2722   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0210    0.5842   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2677    0.7049    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3518    1.9840    1.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3925    2.0949   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8078    1.9062   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -1.9461    1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4055   -1.2093   -0.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    1.8117   -0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030    0.6497   -2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601   -1.0399   -2.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3808   -1.7906   -3.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1597   -0.8255   -1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6008    0.8604   -0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850    1.6121    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661    1.0919    2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -2.9030    1.6412 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  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  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
  8 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28  2  1  0
 25  4  1  0
 19 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  7 35  1  0
 10 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
 24 46  1  0
M  END


  Mrv0541 09061400392D          

 28 30  0  0  0  0            999 V2000
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  4  0  0  0
 22 18  2  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 27 20  2  0  0  0  0
 28 10  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2=C(Cl)C=C(C(O)=NC(CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1

> <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)

> <INCHI_KEY>
RWQKHEORZBHNRI-UHFFFAOYSA-N

> <FORMULA>
C20H18ClNO6

> <MOLECULAR_WEIGHT>
403.813

> <EXACT_MASS>
403.08226502

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
39.19472084918062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
5.430660071

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.640733779804922

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.264727684566722

> <JCHEM_PKA_STRONGEST_BASIC>
0.13720301155653636

> <JCHEM_POLAR_SURFACE_AREA>
116.42000000000003

> <JCHEM_REFRACTIVITY>
102.29169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       5.335   0.000   0.000  0.00  0.00          Cl+0
HETATM   22  N   UNK     0       9.336   3.850   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7   10   12                                                       
CONECT    8   11   15                                                       
CONECT    9   13   14                                                       
CONECT   10    1    7   28                                                  
CONECT   11    5    6    8                                                  
CONECT   12    7   14   16                                                  
CONECT   13    9   17   18                                                  
CONECT   14    9   12   21                                                  
CONECT   15    8   19   22                                                  
CONECT   16   12   17   20                                                  
CONECT   17   13   16   23                                                  
CONECT   18   13   22   24                                                  
CONECT   19   15   25   26                                                  
CONECT   20   16   27   28                                                  
CONECT   21   14                                                            
CONECT   22   15   18                                                       
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   10   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈ClNO₆

Average Mass

403.8130 Da

Monoisotopic Mass

403.08227 Da

IUPAC Name

2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

Traditional Name

2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC1CC2=C(Cl)C=C(C(O)=NC(CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1

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)

InChI Key

RWQKHEORZBHNRI-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aspergillus melleus	LOTUS Database	35616633
Aspergillus ochraceus	LOTUS Database	35616633

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

Not Available

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	3.66	ALOGPS
logP	5.43	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	0.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.29 m³·mol⁻¹	ChemAxon
Polarizability	39.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ochratoxin A

METLIN ID

Not Available

PubChem Compound

4580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid (NP0173623)

MOL for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

3D MOL for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

3D SDF for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

3D-SDF for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

PDB for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

3D PDB for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

SMILES for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

INCHI for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

Structure for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)

3D Structure for NP0173623 (2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid)