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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:19 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041857

Secondary Accession Numbers

HMDB41857

Metabolite Identification

Common Name

Citrinin

Description

Citrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are found or used in the production of human foods, such as grain, cheese, sake and red pigments. Citrinin has also been found in commercial red yeast rice supplements, and also in Aspergillus niveus and Aspergillus terreus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0041857
     RDKit          3D
Citrinin
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.1230   -2.7828    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -1.3860   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453   -0.4084   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.9578   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    1.8999   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    1.5824    0.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.5092    1.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5491    0.8389    2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.7224    0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5912   -0.9813   -0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506    1.2760   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    2.5814   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.3014   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223    0.5351   -1.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -0.4032   -1.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    1.8251   -1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -1.0733   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724   -2.0080   -0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -3.4540   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092   -3.0501    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.9760   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    2.9097   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    0.3558    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -0.0342    2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    1.2342    3.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    1.6713    2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -1.5687    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -0.8806   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.2480   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -1.9863   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8717    2.9589   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.5263   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 16 32  1  0
M  END


  Mrv0541 09051417092D          

 20 21  0  0  1  0            999 V2000
    1.4289    0.8250    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    2.1434   -0.4125    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  6  2  1  0  0  0  0
  7  3  1  6  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18  4  1  0  0  0  0
 18  7  1  0  0  0  0
  5 19  1  6  0  0  0
  7 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041857

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

> <INCHI_KEY>
CQIUKKVOEOPUDV-IYSWYEEDSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.2473

> <EXACT_MASS>
250.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.0128857458919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
0.8089523660000004

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.526015812136112

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5532335821632577

> <JCHEM_PKA_STRONGEST_BASIC>
-4.787666790800133

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
65.2535

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
antimycin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041857
     RDKit          3D
Citrinin
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.1230   -2.7828    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -1.3860   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453   -0.4084   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.9578   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    1.8999   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    1.5824    0.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.5092    1.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5491    0.8389    2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.7224    0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5912   -0.9813   -0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506    1.2760   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    2.5814   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.3014   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223    0.5351   -1.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -0.4032   -1.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    1.8251   -1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -1.0733   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724   -2.0080   -0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -3.4540   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092   -3.0501    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.9760   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    2.9097   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    0.3558    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -0.0342    2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    1.2342    3.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    1.6713    2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -1.5687    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -0.8806   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.2480   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -1.9863   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8717    2.9589   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.5263   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8   18                                                       
CONECT    5    1    7    9   19                                             
CONECT    6    2    9   11                                                  
CONECT    7    3    5   18   20                                             
CONECT    8    4    9   12                                                  
CONECT    9    5    6    8                                                  
CONECT   10   11   12   13                                                  
CONECT   11    6   10   14                                                  
CONECT   12    8   10   15                                                  
CONECT   13   10   16   17                                                  
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18    4    7                                                       
CONECT   19    5                                                            
CONECT   20    7                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0041857
HETATM    1  C1  UNL     1       0.123  -2.783   0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.555  -1.386  -0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.345  -0.408  -0.002  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.087   0.958  -0.312  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.840   1.900  -0.202  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.146   1.582   0.188  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.293   0.509   1.102  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.549   0.839   2.370  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.743  -0.722   0.411  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.591  -0.981  -0.808  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.451   1.276  -0.717  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.823   2.581  -1.002  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.337   0.301  -0.811  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.722   0.535  -1.210  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.529  -0.403  -1.288  1.00  0.00           O  
HETATM   16  O4  UNL     1       4.118   1.825  -1.499  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.908  -1.073  -0.501  1.00  0.00           C  
HETATM   18  O5  UNL     1       2.772  -2.008  -0.595  1.00  0.00           O  
HETATM   19  H1  UNL     1       0.771  -3.454  -0.407  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.309  -3.050   1.272  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.910  -2.976  -0.078  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.528   2.910  -0.429  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.373   0.356   1.301  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.046  -0.034   2.822  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.278   1.234   3.120  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.822   1.671   2.198  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.762  -1.569   1.129  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.959  -0.881  -1.724  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.419  -0.248  -0.913  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.058  -1.986  -0.793  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.872   2.959  -1.937  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.285   2.526  -0.799  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4    9
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7
CONECT    7    8    9   23
CONECT    8   24   25   26
CONECT    9   10   27
CONECT   10   28   29   30
CONECT   11   12   13   13
CONECT   12   31
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   16   32
CONECT   17   18   18
END

HMDB0041857
     RDKit          3D
Citrinin
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.1230   -2.7828    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -1.3860   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453   -0.4084   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.9578   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    1.8999   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    1.5824    0.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.5092    1.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5491    0.8389    2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.7224    0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5912   -0.9813   -0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506    1.2760   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    2.5814   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.3014   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223    0.5351   -1.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -0.4032   -1.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    1.8251   -1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -1.0733   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724   -2.0080   -0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -3.4540   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092   -3.0501    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.9760   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    2.9097   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    0.3558    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -0.0342    2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    1.2342    3.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    1.6713    2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -1.5687    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -0.8806   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.2480   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -1.9863   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8717    2.9589   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.5263   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid	ChEBI
(3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid	ChEBI
(3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylate	Generator
(3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylate	Generator
(3R,4S)-8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid	HMDB
Antimycin	HMDB
Citriain	HMDB
Citrinin	ChEBI

Chemical Formula

C₁₃H₁₄O₅

Average Molecular Weight

250.2473

Monoisotopic Molecular Weight

250.084123558

IUPAC Name

(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid

Traditional Name

antimycin

CAS Registry Number

518-75-2

SMILES

[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C

InChI Identifier

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

InChI Key

CQIUKKVOEOPUDV-IYSWYEEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

citrinin (CHEBI:48707 )
Mycotoxins (C16765 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	24090 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	150.202	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001137

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.16 g/L	ALOGPS
logP	1.23	ALOGPS
logP	0.81	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.25 m³·mol⁻¹	ChemAxon
Polarizability	25.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	157.046	30932474
DeepCCS	[M-H]-	154.688	30932474
DeepCCS	[M-2H]-	188.336	30932474
DeepCCS	[M+Na]+	163.512	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrinin	[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C	3416.5	Standard polar	33892256
Citrinin	[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C	1779.7	Standard non polar	33892256
Citrinin	[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C	2045.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citrinin,1TMS,isomer #1	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C)=C(C(=O)O)C1=O	2055.9	Semi standard non polar	33892256
Citrinin,1TMS,isomer #2	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O)=C(C(=O)O[Si](C)(C)C)C1=O	2036.4	Semi standard non polar	33892256
Citrinin,2TMS,isomer #1	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C1=O	2107.3	Semi standard non polar	33892256
Citrinin,1TBDMS,isomer #1	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)O)C1=O	2290.3	Semi standard non polar	33892256
Citrinin,1TBDMS,isomer #2	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O)=C(C(=O)O[Si](C)(C)C(C)(C)C)C1=O	2265.6	Semi standard non polar	33892256
Citrinin,2TBDMS,isomer #1	CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C1=O	2523.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citrinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-07ii-1950000000-bf6353469eb59dfd035e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrinin GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3409000000-998272da21093d63d473	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin LC-ESI-qToF , Positive-QTOF	splash10-001i-0290000000-19d08795fea7c80d6d85	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin , positive-QTOF	splash10-001i-0290000000-19d08795fea7c80d6d85	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 40V, Negative-QTOF	splash10-056r-0910000000-dc73977534605fabc153	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 20V, Negative-QTOF	splash10-0a6r-0980000000-0b8bfd0f8f61fc57c4a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 10V, Negative-QTOF	splash10-0002-0290000000-7d633abf71a04d44c8d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 40V, Positive-QTOF	splash10-066r-0920000000-707727c1075dd45d7108	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 10V, Positive-QTOF	splash10-0f89-0090000000-d154c54944621174eae4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citrinin 20V, Positive-QTOF	splash10-001i-0090000000-fe2b94b81a1bd47da23c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 10V, Positive-QTOF	splash10-0udi-0090000000-448b730e55729839783f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 20V, Positive-QTOF	splash10-0pc0-1390000000-b2d7bec5177df13bf6b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 40V, Positive-QTOF	splash10-0udi-9400000000-8c38a7814bc7b5aa2429	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 10V, Negative-QTOF	splash10-0a4j-0090000000-cca6d7a143b768fc5b3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 20V, Negative-QTOF	splash10-0a4i-0390000000-4f2f5c7982385791b46f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 40V, Negative-QTOF	splash10-015j-3910000000-b3cbc912af168ecaeb68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 10V, Negative-QTOF	splash10-052b-0090000000-27ccf87acb59e5348617	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 20V, Negative-QTOF	splash10-0a4j-0190000000-b3dc2138a209a34bc5d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 40V, Negative-QTOF	splash10-000i-1900000000-488f0638f8ef7fb1568f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 10V, Positive-QTOF	splash10-0ue9-0090000000-719d816638185ee9f2d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 20V, Positive-QTOF	splash10-001i-0090000000-e68e48c0c6d1b9e9fce4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrinin 40V, Positive-QTOF	splash10-0ll1-7790000000-34420a63944577cbd887	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00029979

Chemspider ID

10222475

KEGG Compound ID

C16765

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citrinin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

48707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1230771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Citrinin (HMDB0041857)

MOL for HMDB0041857 (Citrinin)

3D MOL for HMDB0041857 (Citrinin)

3D SDF for HMDB0041857 (Citrinin)

3D-SDF for HMDB0041857 (Citrinin)

PDB for HMDB0041857 (Citrinin)

3D PDB for HMDB0041857 (Citrinin)

SMILES for HMDB0041857 (Citrinin)

INCHI for HMDB0041857 (Citrinin)

Structure for HMDB0041857 (Citrinin)

3D Structure for HMDB0041857 (Citrinin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra