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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:09:07 UTC

Update Date

2022-03-07 02:55:55 UTC

HMDB ID

HMDB0038806

Secondary Accession Numbers

HMDB38806

Metabolite Identification

Common Name

Aflatoxin M4

Description

Aflatoxin M4 is a metabolite of Aspergillus flavus and Aspergillus parasiticus (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

HMDB0038806
     RDKit          3D
Aflatoxin M4
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.4901    3.2036    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    1.9081    1.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.2100    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466    1.7401    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    0.9810    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8864   -0.2846    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -0.8370   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -2.0672   -0.5825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -2.5642   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8199   -3.7407   -1.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -1.8628   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.5957    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -0.0765    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456   -0.0361    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -1.0214   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.5011   -1.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -2.2375   -0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -3.3655   -0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.7968   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6719   -0.5373   -1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.0636   -1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    0.2402   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341    0.1387    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    1.3186    0.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496    3.2422    2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.8603    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620    3.5464    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    2.7380    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.9504   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    0.1206    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.2446    0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.0023   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.8544    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334   -0.7823   -2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    0.3849   -2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.2388    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 19  1  0
 24  5  1  0
 13  7  2  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END


  Mrv0541 05061310402D          

 24 28  0  0  0  0            999 V2000
    7.7893    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -0.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9910    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098    1.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2478    0.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5613   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3733    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    1.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684    0.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4843    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589   -0.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1706   -0.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319   -0.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7064   -1.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3788    0.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5289   -1.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8174   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0258    1.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117    0.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    1.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429   -0.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  2  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22  3  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 15  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038806

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)C(O)C1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O7/c1-21-9-5-10-11(6-2-3-22-17(6)23-10)15-12(9)7-4-8(18)14(19)13(7)16(20)24-15/h2-3,5-6,8,17-18H,4H2,1H3

> <INCHI_KEY>
JUJRETIUKMEFIA-UHFFFAOYSA-N

> <FORMULA>
C17H12O7

> <MOLECULAR_WEIGHT>
328.273

> <EXACT_MASS>
328.058302738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.143528020448954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.7133149823333332

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.262902189233554

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5577785788175804

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
80.07730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038806
     RDKit          3D
Aflatoxin M4
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.4901    3.2036    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    1.9081    1.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.2100    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466    1.7401    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    0.9810    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8864   -0.2846    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -0.8370   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -2.0672   -0.5825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -2.5642   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8199   -3.7407   -1.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -1.8628   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.5957    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -0.0765    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456   -0.0361    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -1.0214   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.5011   -1.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -2.2375   -0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -3.3655   -0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.7968   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6719   -0.5373   -1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.0636   -1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    0.2402   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341    0.1387    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    1.3186    0.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496    3.2422    2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.8603    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620    3.5464    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    2.7380    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.9504   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    0.1206    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.2446    0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.0023   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.8544    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334   -0.7823   -2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    0.3849   -2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.2388    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 19  1  0
 24  5  1  0
 13  7  2  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      14.540   2.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.344  -1.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.829  -1.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.917   0.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.472   3.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.074  -0.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.529   0.326   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.981  -0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.897   2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.254   2.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.461   0.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.104   0.910   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.737  -1.200   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.252  -1.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.886  -0.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.519  -2.142   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.009   0.995   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.507   0.089   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      15.921  -2.861   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.726  -3.668   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.115   3.378   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.622   0.326   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.738   2.351   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.093  -1.559   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    6                                                       
CONECT    3    2   22                                                       
CONECT    4    7    8                                                       
CONECT    5    9   10                                                       
CONECT    6    2   11   17                                                  
CONECT    7    4   12   13                                                  
CONECT    8    4   14   18                                                  
CONECT    9    5   12   21                                                  
CONECT   10    5   11   23                                                  
CONECT   11    6   10   15                                                  
CONECT   12    7    9   15                                                  
CONECT   13    7   14   16                                                  
CONECT   14    8   13   19                                                  
CONECT   15   11   12   24                                                  
CONECT   16   13   20   24                                                  
CONECT   17    6   22   23                                                  
CONECT   18    8                                                            
CONECT   19   14                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22    3   17                                                       
CONECT   23   10   17                                                       
CONECT   24   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0038806
HETATM    1  C1  UNL     1      -1.490   3.204   1.585  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.445   1.908   1.076  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.318   1.210   0.742  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.947   1.740   0.881  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.033   0.981   0.525  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.886  -0.285   0.039  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.634  -0.837  -0.109  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.499  -2.067  -0.583  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.704  -2.564  -0.711  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.820  -3.741  -1.165  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.864  -1.863  -0.375  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.759  -0.596   0.115  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.457  -0.077   0.247  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.046  -0.036   0.401  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.039  -1.021  -0.174  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.647  -0.501  -1.317  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.259  -2.238  -0.443  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.758  -3.365  -0.682  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.254  -0.797  -0.235  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.672  -0.537  -1.633  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.848   0.064  -1.631  1.00  0.00           C  
HETATM   22  O6  UNL     1       5.278   0.240  -0.302  1.00  0.00           O  
HETATM   23  C17 UNL     1       4.134   0.139   0.547  1.00  0.00           C  
HETATM   24  O7  UNL     1       3.386   1.319   0.584  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.150   3.242   2.643  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.902   3.860   0.919  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.562   3.546   1.521  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.038   2.738   1.266  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.185   0.950  -0.128  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.321   0.121   1.450  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.872  -1.245   0.547  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.342  -1.002  -2.132  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.375  -1.854   0.047  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.133  -0.782  -2.555  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.421   0.385  -2.506  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.401  -0.239   1.549  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   19
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   14   15   29   30
CONECT   15   16   17   31
CONECT   16   32
CONECT   17   18   18
CONECT   19   20   23   33
CONECT   20   21   21   34
CONECT   21   22   35
CONECT   22   23
CONECT   23   24   36
END

HMDB0038806
     RDKit          3D
Aflatoxin M4
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.4901    3.2036    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    1.9081    1.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.2100    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466    1.7401    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    0.9810    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8864   -0.2846    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -0.8370   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -2.0672   -0.5825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -2.5642   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8199   -3.7407   -1.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -1.8628   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.5957    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -0.0765    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456   -0.0361    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -1.0214   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.5011   -1.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -2.2375   -0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -3.3655   -0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.7968   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6719   -0.5373   -1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.0636   -1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    0.2402   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341    0.1387    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    1.3186    0.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496    3.2422    2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.8603    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620    3.5464    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    2.7380    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.9504   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    0.1206    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.2446    0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.0023   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.8544    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334   -0.7823   -2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    0.3849   -2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.2388    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 19  1  0
 24  5  1  0
 13  7  2  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₂O₇

Average Molecular Weight

328.273

Monoisotopic Molecular Weight

328.058302738

IUPAC Name

15-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

Traditional Name

15-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

CAS Registry Number

104700-21-2

SMILES

COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)C(O)C1)C(=O)O2

InChI Identifier

InChI=1S/C17H12O7/c1-21-9-5-10-11(6-2-3-22-17(6)23-10)15-12(9)7-4-8(18)14(19)13(7)16(20)24-15/h2-3,5-6,8,17-18H,4H2,1H3

InChI Key

JUJRETIUKMEFIA-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Difurocoumarocyclopentenones

Alternative Parents

Substituents

Difurocoumarocyclopentenone
Benzopyran
1-benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Dihydrofuran
Heteroaromatic compound
Secondary alcohol
Lactone
Ketone
Acetal
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038806)
Cytoplasm (HMDB: HMDB0038806)

Source

Exogenous

Food

Food (HMDB: HMDB0038806)

Endogenous

Plant

Plant (HMDB: HMDB0038806)

Fungi

Aspergillus flavus (HMDB: HMDB0038806)
Aspergillus parasiticus (HMDB: HMDB0038806)

Not Available

Nutrient (HMDB: HMDB0038806)

Environmental role

Environmental contaminant (HMDB: HMDB0038806)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.9 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.71	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.08 m³·mol⁻¹	ChemAxon
Polarizability	31.14 Å³	ChemAxon
Number of Rings	5	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
DarkChem	[M+H]+	174.879	31661259
DarkChem	[M-H]-	173.655	31661259
DeepCCS	[M+H]+	178.428	30932474
DeepCCS	[M-H]-	176.07	30932474
DeepCCS	[M-2H]-	210.269	30932474
DeepCCS	[M+Na]+	186.434	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin M4	COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)C(O)C1)C(=O)O2	4456.8	Standard polar	33892256
Aflatoxin M4	COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)C(O)C1)C(=O)O2	2963.6	Standard non polar	33892256
Aflatoxin M4	COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)C(O)C1)C(=O)O2	2968.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin M4,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C(O[Si](C)(C)C)C1)C(=O)O3)C1C=COC1O2	3034.0	Semi standard non polar	33892256
Aflatoxin M4,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C(O[Si](C)(C)C(C)(C)C)C1)C(=O)O3)C1C=COC1O2	3258.2	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 - Aflatoxin M4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0092000000-56f93143fbf5fe7d6d2a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin M4 GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3009000000-3c6c94c3bb7d1af8340f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin M4 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 10V, Positive-QTOF	splash10-004i-0019000000-b44cc9e35c8afc9a53df	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 20V, Positive-QTOF	splash10-01r2-0096000000-63dbeb7a01dba1123598	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 40V, Positive-QTOF	splash10-00pi-0190000000-556bb5c3e0df9f373b54	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 10V, Negative-QTOF	splash10-004i-0039000000-b707787eb191be1dba23	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 20V, Negative-QTOF	splash10-004i-0069000000-65225931f0525c7ad30b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 40V, Negative-QTOF	splash10-014i-2090000000-7b313dcc881bd7a6ed3c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 10V, Positive-QTOF	splash10-004i-0009000000-a6e8d4715f87e5602d4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 20V, Positive-QTOF	splash10-004i-0009000000-6f57e7e956a93fb6afc9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 40V, Positive-QTOF	splash10-052b-0091000000-7c1fcdf46552f9c77939	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 10V, Negative-QTOF	splash10-004i-0009000000-3eb691afb29ed57b3f5f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 20V, Negative-QTOF	splash10-004i-0019000000-25b8b0d98daeed7cf768	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M4 40V, Negative-QTOF	splash10-0002-0391000000-05673a9c5ebfb7552738	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018231

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92043985

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Aflatoxin M4 (HMDB0038806)

MOL for HMDB0038806 (Aflatoxin M4)

3D MOL for HMDB0038806 (Aflatoxin M4)

3D SDF for HMDB0038806 (Aflatoxin M4)

3D-SDF for HMDB0038806 (Aflatoxin M4)

PDB for HMDB0038806 (Aflatoxin M4)

3D PDB for HMDB0038806 (Aflatoxin M4)

SMILES for HMDB0038806 (Aflatoxin M4)

INCHI for HMDB0038806 (Aflatoxin M4)

Structure for HMDB0038806 (Aflatoxin M4)

3D Structure for HMDB0038806 (Aflatoxin M4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra