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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:36:27 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035598

Secondary Accession Numbers

HMDB35598

Metabolite Identification

Common Name

Aflatoxin B2a

Description

Aflatoxin B2a 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. Aflatoxin B2a is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxin B2a 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

HMDB0035598
     RDKit          3D
Aflatoxin B2a
 38 42  0  0  0  0  0  0  0  0999 V2000
   -2.0540    3.5952    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1787    2.1892    0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    1.4282   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.0411   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400    1.2784   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.0963   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -0.6925   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663   -1.9941   -0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -2.6032   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -3.8642   -0.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -1.9049   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847   -0.5259   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.0607   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7368   -0.0702    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -1.2466    0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032   -2.3683    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -3.4448   -0.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -0.5789   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -0.9956    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -0.6696    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461   -0.6381    1.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484    0.5335   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4467    0.6325   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    1.6897   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3576    3.8942    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    3.9094   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    4.1027    0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194    3.1222   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    0.0290   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.8706    0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711   -1.3458    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5383   -1.2164    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3770   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -0.3172    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1587   -2.0621    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -1.4749   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844   -0.6581    1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.7682   -2.0995 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
 16 17  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 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
 15 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
M  END


  Mrv0541 05061308352D          

 24 28  0  0  0  0            999 V2000
    5.8379    1.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0396    2.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832    3.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585    1.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965    2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739    3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193    3.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    1.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0060    1.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1714    3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5330    2.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1170    2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805    3.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550    4.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    2.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5775    4.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5753    4.2778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660    5.0298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0744    1.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942    1.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    2.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    3.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14 10  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  2  0  0  0  0
 19 11  1  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 10  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  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>
HMDB0035598

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C3CC(O)OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-21-9-5-10-14(7-4-11(19)23-17(7)22-10)15-13(9)6-2-3-8(18)12(6)16(20)24-15/h5,7,11,17,19H,2-4H2,1H3

> <INCHI_KEY>
PFQSKXVNBUHPIW-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.13795924224501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
0.9794764503333332

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.789076897104533

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.379197650439554

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9451382081815725

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
79.6323

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035598
     RDKit          3D
Aflatoxin B2a
 38 42  0  0  0  0  0  0  0  0999 V2000
   -2.0540    3.5952    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1787    2.1892    0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    1.4282   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.0411   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400    1.2784   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.0963   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -0.6925   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663   -1.9941   -0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -2.6032   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -3.8642   -0.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -1.9049   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847   -0.5259   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.0607   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7368   -0.0702    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -1.2466    0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032   -2.3683    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -3.4448   -0.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -0.5789   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -0.9956    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -0.6696    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461   -0.6381    1.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484    0.5335   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4467    0.6325   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    1.6897   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3576    3.8942    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    3.9094   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    4.1027    0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194    3.1222   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    0.0290   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.8706    0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711   -1.3458    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5383   -1.2164    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3770   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -0.3172    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1587   -2.0621    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -1.4749   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844   -0.6581    1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.7682   -2.0995 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
 16 17  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 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
 15 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  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      10.897   2.926   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.274   4.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.339   5.839   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.702   7.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.829   2.702   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.887   5.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.431   5.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.609   7.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.254   3.285   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.611   3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.187   6.921   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.094   6.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.462   4.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.818   5.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.244   5.753   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.876   7.863   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.367   4.726   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.278   8.582   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.074   7.985   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.083   9.389   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.472   2.343   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.096   3.370   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.979   5.395   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.451   7.279   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    7   11                                                       
CONECT    5    9   10                                                       
CONECT    6    2   12   13                                                  
CONECT    7    4   14   17                                                  
CONECT    8    3   12   18                                                  
CONECT    9    5   13   21                                                  
CONECT   10    5   14   22                                                  
CONECT   11    4   19   23                                                  
CONECT   12    6    8   16                                                  
CONECT   13    6    9   15                                                  
CONECT   14    7   10   15                                                  
CONECT   15   13   14   24                                                  
CONECT   16   12   20   24                                                  
CONECT   17    7   22   23                                                  
CONECT   18    8                                                            
CONECT   19   11                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22   10   17                                                       
CONECT   23   11   17                                                       
CONECT   24   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0035598
HETATM    1  C1  UNL     1      -2.054   3.595   0.166  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.179   2.189   0.096  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.061   1.428  -0.080  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.193   2.041  -0.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.340   1.278  -0.371  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.243  -0.096  -0.443  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.014  -0.692  -0.334  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.066  -1.994  -0.404  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.220  -2.603  -0.306  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.247  -3.864  -0.379  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.400  -1.905  -0.124  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.385  -0.526  -0.043  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.116   0.061  -0.156  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.737  -0.070   0.137  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.449  -1.247   0.771  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.803  -2.368   0.018  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.278  -3.445  -0.408  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.611  -0.579  -0.634  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.289  -0.996   0.660  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.740  -0.670   0.283  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.546  -0.638   1.417  1.00  0.00           O  
HETATM   22  O6  UNL     1       4.648   0.533  -0.368  1.00  0.00           O  
HETATM   23  C17 UNL     1       3.447   0.633  -1.009  1.00  0.00           C  
HETATM   24  O7  UNL     1       2.658   1.690  -0.501  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.358   3.894   0.996  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.611   3.909  -0.824  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.033   4.103   0.237  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.219   3.122  -0.129  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.204   0.029  -0.889  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.950   0.871   0.638  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.171  -1.346   1.855  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.538  -1.216   0.626  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.708  -1.377  -1.389  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.949  -0.317   1.440  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.159  -2.062   0.874  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.090  -1.475  -0.391  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.484  -0.658   1.095  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.521   0.768  -2.099  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   18
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   14
CONECT   14   15   29   30
CONECT   15   16   31   32
CONECT   16   17   17
CONECT   18   19   23   33
CONECT   19   20   34   35
CONECT   20   21   22   36
CONECT   21   37
CONECT   22   23
CONECT   23   24   38
END

HMDB0035598
     RDKit          3D
Aflatoxin B2a
 38 42  0  0  0  0  0  0  0  0999 V2000
   -2.0540    3.5952    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1787    2.1892    0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    1.4282   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.0411   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400    1.2784   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.0963   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -0.6925   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663   -1.9941   -0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -2.6032   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -3.8642   -0.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -1.9049   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847   -0.5259   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.0607   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7368   -0.0702    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -1.2466    0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032   -2.3683    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -3.4448   -0.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -0.5789   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -0.9956    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -0.6696    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461   -0.6381    1.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484    0.5335   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4467    0.6325   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    1.6897   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3576    3.8942    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    3.9094   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    4.1027    0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194    3.1222   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    0.0290   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.8706    0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711   -1.3458    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5383   -1.2164    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3770   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -0.3172    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1587   -2.0621    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -1.4749   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844   -0.6581    1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.7682   -2.0995 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
 16 17  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 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
 15 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aflatoxin b1, hemiacetal	HMDB
Dihydrohydroxy-aflatoxin b1	HMDB
Dihydrohydroxyaflatoxin b1	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

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

Traditional Name

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

CAS Registry Number

17878-54-5

SMILES

COC1=CC2=C(C3CC(O)OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

InChI Identifier

InChI=1S/C17H14O7/c1-21-9-5-10-14(7-4-11(19)23-17(7)22-10)15-13(9)6-2-3-8(18)12(6)16(20)24-15/h5,7,11,17,19H,2-4H2,1H3

InChI Key

PFQSKXVNBUHPIW-UHFFFAOYSA-N

Chemical Taxonomy

Description

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
Difurocoumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Lactone
Ketone
Hemiacetal
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035598)
Cytoplasm (HMDB: HMDB0035598)

Source

Exogenous

Food

Food (HMDB: HMDB0035598)

Endogenous

Plant

Plant (HMDB: HMDB0035598)

Fungi

Aspergillus flavus (HMDB: HMDB0035598)
Aspergillus parasiticus (HMDB: HMDB0035598)

Not Available

Nutrient (HMDB: HMDB0035598)

Environmental role

Environmental contaminant (HMDB: HMDB0035598)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 °C	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	1.44 g/L	ALOGPS
logP	0.96	ALOGPS
logP	0.98	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.9	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	79.63 m³·mol⁻¹	ChemAxon
Polarizability	32.14 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]+	177.163	31661259
DarkChem	[M-H]-	173.457	31661259
DeepCCS	[M+H]+	176.519	30932474
DeepCCS	[M-H]-	174.161	30932474
DeepCCS	[M-2H]-	208.048	30932474
DeepCCS	[M+Na]+	183.275	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.0	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin B2a	COC1=CC2=C(C3CC(O)OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	4231.6	Standard polar	33892256
Aflatoxin B2a	COC1=CC2=C(C3CC(O)OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	2984.7	Standard non polar	33892256
Aflatoxin B2a	COC1=CC2=C(C3CC(O)OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	3173.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin B2a,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)C1CC(O[Si](C)(C)C)OC1O2	3040.0	Semi standard non polar	33892256
Aflatoxin B2a,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)C1CC(O[Si](C)(C)C(C)(C)C)OC1O2	3278.5	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 B2a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gw0-0093000000-72aebab5bc1464e2b671	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B2a GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-9287000000-d076aaed5db918895061	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B2a 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 B2a 10V, Positive-QTOF	splash10-001i-0019000000-9ed7cc899db39716068b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 20V, Positive-QTOF	splash10-01q9-0098000000-caf6d1df7d891b669820	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 40V, Positive-QTOF	splash10-00lr-4190000000-93cba69960ec3ad5bdc5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 10V, Negative-QTOF	splash10-004i-0089000000-59450bcef8d92a2d910d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 20V, Negative-QTOF	splash10-01u0-0089000000-4c498e0e44571e4d85d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 40V, Negative-QTOF	splash10-0gec-2090000000-8d96f2e31d1541ac0147	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 10V, Negative-QTOF	splash10-004i-0009000000-c574fa658a65fe6898a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 20V, Negative-QTOF	splash10-004i-0079000000-245002d02f05fda88f7f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 40V, Negative-QTOF	splash10-002b-1294000000-ff6a063d7b9247f1a4a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 10V, Positive-QTOF	splash10-001i-0009000000-931b28fcfeb1b8f804fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 20V, Positive-QTOF	splash10-001i-0009000000-f0c8ea7f0bc28f9b7eef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2a 40V, Positive-QTOF	splash10-0udi-0079000000-cd83dd273656280564e0	2021-09-24	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

FDB014291

KNApSAcK ID

Not Available

Chemspider ID

28555046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14252429

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 B2a (HMDB0035598)

MOL for HMDB0035598 (Aflatoxin B2a)

3D MOL for HMDB0035598 (Aflatoxin B2a)

3D SDF for HMDB0035598 (Aflatoxin B2a)

3D-SDF for HMDB0035598 (Aflatoxin B2a)

PDB for HMDB0035598 (Aflatoxin B2a)

3D PDB for HMDB0035598 (Aflatoxin B2a)

SMILES for HMDB0035598 (Aflatoxin B2a)

INCHI for HMDB0035598 (Aflatoxin B2a)

Structure for HMDB0035598 (Aflatoxin B2a)

3D Structure for HMDB0035598 (Aflatoxin B2a)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra