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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:09:29 UTC

Update Date

2022-03-07 02:54:24 UTC

HMDB ID

HMDB0035208

Secondary Accession Numbers

HMDB35208

Metabolite Identification

Common Name

Aflatoxin B2

Description

Aflatoxin B2 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 B2 is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Aflatoxin B2.

Structure

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

HMDB0035208
     RDKit          3D
Aflatoxin B2
 37 41  0  0  0  0  0  0  0  0999 V2000
   -2.4013    3.2692   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650    1.8656   -0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033    1.3225    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058    2.1161    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3614    1.5309    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.1564    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3326   -0.6524    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.9751    0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -2.7437    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608   -4.0152    0.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8545   -2.1970   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -0.8363   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.0571    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421   -0.4584   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116   -1.7537   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -2.7974   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233   -4.0454   -0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -0.2494    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.7240   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.1344   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977    1.1492   -0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637    1.0656    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    2.0797    0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4548    3.5879   -0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9166    3.6641    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    3.6941   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0056    3.2006    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    0.2208    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    0.0675   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8511   -1.8023    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8910   -1.8143   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.9568    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.8238   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.2389   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850   -0.1331   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -0.7079    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    1.1266    1.8250 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
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
M  END


  Mrv0541 09061400492D          

 23 27  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
    1.1714    3.7075    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
    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
    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
    1.0604    2.8900    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
    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
  5  4  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  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  8  1  0  0  0  0
 18  9  2  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21  5  1  0  0  0  0
 21 17  1  0  0  0  0
 22 11  1  0  0  0  0
 22 17  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035208

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h6,8,17H,2-5H2,1H3

> <INCHI_KEY>
WWSYXEZEXMQWHT-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.896329339061317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
1.63

> <JCHEM_LOGP>
1.5724018579999992

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.788992235535716

> <JCHEM_PKA_STRONGEST_BASIC>
-4.149809499814798

> <JCHEM_POLAR_SURFACE_AREA>
71.06000000000002

> <JCHEM_REFRACTIVITY>
78.492

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aflatoxin B2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035208
     RDKit          3D
Aflatoxin B2
 37 41  0  0  0  0  0  0  0  0999 V2000
   -2.4013    3.2692   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650    1.8656   -0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033    1.3225    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058    2.1161    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3614    1.5309    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.1564    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3326   -0.6524    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.9751    0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -2.7437    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608   -4.0152    0.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8545   -2.1970   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -0.8363   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.0571    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421   -0.4584   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116   -1.7537   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -2.7974   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233   -4.0454   -0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -0.2494    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.7240   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.1344   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977    1.1492   -0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637    1.0656    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    2.0797    0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4548    3.5879   -0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9166    3.6641    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    3.6941   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0056    3.2006    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    0.2208    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    0.0675   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8511   -1.8023    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8910   -1.8143   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.9568    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.8238   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.2389   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850   -0.1331   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -0.7079    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    1.1266    1.8250 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
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
M  END

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      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       2.187   6.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.829   2.702   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.887   5.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.431   5.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.609   7.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.254   3.285   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.611   3.644   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   5.754   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       9.083   9.389   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.472   2.343   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.979   5.395   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       7.451   7.280   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    9                                                       
CONECT    4    5    8                                                       
CONECT    5    4   21                                                       
CONECT    6   10   11                                                       
CONECT    7    2   12   13                                                  
CONECT    8    4   14   17                                                  
CONECT    9    3   12   18                                                  
CONECT   10    6   13   20                                                  
CONECT   11    6   14   22                                                  
CONECT   12    7    9   16                                                  
CONECT   13    7   10   15                                                  
CONECT   14    8   11   15                                                  
CONECT   15   13   14   23                                                  
CONECT   16   12   19   23                                                  
CONECT   17    8   21   22                                                  
CONECT   18    9                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21    5   17                                                       
CONECT   22   11   17                                                       
CONECT   23   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0035208
HETATM    1  C1  UNL     1      -2.401   3.269  -0.145  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.265   1.866  -0.138  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.003   1.323   0.028  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.106   2.116   0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.361   1.531   0.348  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.452   0.156   0.350  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.333  -0.652   0.193  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.454  -1.975   0.199  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.597  -2.744   0.051  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.461  -4.015   0.060  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.855  -2.197  -0.114  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.042  -0.836  -0.129  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.903  -0.057   0.031  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.442  -0.458  -0.315  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.212  -1.754  -0.265  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.168  -2.797  -0.296  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.323  -4.045  -0.453  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.865  -0.249   0.537  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.511  -0.724  -0.742  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.915  -0.134  -0.551  1.00  0.00           C  
HETATM   21  O5  UNL     1       4.598   1.149  -0.143  1.00  0.00           O  
HETATM   22  C17 UNL     1       3.564   1.066   0.771  1.00  0.00           C  
HETATM   23  O6  UNL     1       2.612   2.080   0.521  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.455   3.588  -0.200  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.917   3.664   0.780  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.838   3.694  -1.020  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.006   3.201   0.179  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.826   0.221   0.501  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.650   0.068  -1.256  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.851  -1.802   0.636  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.891  -1.814  -1.154  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.005  -0.957   1.378  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.548  -1.824  -0.819  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.983  -0.239  -1.585  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.485  -0.133  -1.475  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.368  -0.708   0.274  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.934   1.127   1.825  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   27
CONECT    5    6    6   23
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   28   29
CONECT   15   16   30   31
CONECT   16   17   17
CONECT   18   19   22   32
CONECT   19   20   33   34
CONECT   20   21   35   36
CONECT   21   22
CONECT   22   23   37
END

HMDB0035208
     RDKit          3D
Aflatoxin B2
 37 41  0  0  0  0  0  0  0  0999 V2000
   -2.4013    3.2692   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650    1.8656   -0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033    1.3225    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058    2.1161    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3614    1.5309    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.1564    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3326   -0.6524    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.9751    0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -2.7437    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608   -4.0152    0.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8545   -2.1970   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -0.8363   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.0571    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421   -0.4584   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116   -1.7537   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -2.7974   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233   -4.0454   -0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -0.2494    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.7240   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.1344   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977    1.1492   -0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637    1.0656    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    2.0797    0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4548    3.5879   -0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9166    3.6641    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    3.6941   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0056    3.2006    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    0.2208    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    0.0675   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8511   -1.8023    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8910   -1.8143   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.9568    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.8238   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.2389   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850   -0.1331   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -0.7079    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    1.1266    1.8250 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
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aflatoxin b2, (6ar-cis)-isomer	MeSH
Aflatoxin b2 alpha	HMDB
Dihydroafflatoxin b1	HMDB
Dihydroaflatoxin b1	HMDB
Dihydroaflatoxine b1	HMDB
Aflatoxin b2	MeSH

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

IUPAC Name

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

aflatoxin B2

CAS Registry Number

7220-81-7

SMILES

COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

InChI Identifier

InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h6,8,17H,2-5H2,1H3

InChI Key

WWSYXEZEXMQWHT-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
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a secondary metabolite (CPD-10177 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatitis (HMDB: HMDB0035208)
Hepatocellular carcinoma (HMDB: HMDB0035208)

Gastrointestinal disorder

Vomiting (HMDB: HMDB0035208)
Abdominal pain (HMDB: HMDB0035208)

Skin and subcutaneous tissue disorder

Erythema (HMDB: HMDB0035208)

Nervous system disorder

Peripheral nervous system disorder

Sympathetic nervous system disorder

Visual system disorder

Reye's syndrome (HMDB: HMDB0035208)

Cancer

Cancer (HMDB: HMDB0035208)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035208)
Cytoplasm (HMDB: HMDB0035208)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0035208)
Inhalation (HMDB: HMDB0035208)

Enteral

Ingestion (HMDB: HMDB0035208)

Source

Exogenous

Food

Food (HMDB: HMDB0035208)

Endogenous

Plant

Plant (HMDB: HMDB0035208)

Fungi

Aspergillus flavus (HMDB: HMDB0035208)
Aspergillus parasiticus (HMDB: HMDB0035208)

Not Available

Nutrient (HMDB: HMDB0035208)

Indirect biological role

Carcinogen (HMDB: HMDB0035208)

Environmental role

Environmental contaminant (HMDB: HMDB0035208)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	310 °C	Not Available
Boiling Point	521.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	585.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.802 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.57	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.49 m³·mol⁻¹	ChemAxon
Polarizability	30.9 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]+	173.523	31661259
DarkChem	[M-H]-	170.284	31661259
DeepCCS	[M+H]+	176.715	30932474
DeepCCS	[M-H]-	174.357	30932474
DeepCCS	[M-2H]-	208.006	30932474
DeepCCS	[M+Na]+	183.391	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.7	32859911
AllCCS	[M+Na]+	174.6	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	176.2	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin B2	COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	4097.2	Standard polar	33892256
Aflatoxin B2	COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	2810.2	Standard non polar	33892256
Aflatoxin B2	COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2	3049.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Aflatoxin B2 EI-B (Non-derivatized)	splash10-03di-0039000000-610151efc4e68c6939eb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aflatoxin B2 EI-B (Non-derivatized)	splash10-03di-0039000000-610151efc4e68c6939eb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0080-0190000000-cdd965c2769a1d578fba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-4189000000-6bab374050b1044ec494	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 50V, Positive-QTOF	splash10-0a4l-0390000000-85aa7a411b52bfa748ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 20V, Positive-QTOF	splash10-014i-0009000000-306b14c6051334a7615d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 10V, Positive-QTOF	splash10-014i-0009000000-6117c5ee93218e1f3ee4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 30V, Positive-QTOF	splash10-014i-0069000000-e8cfaba3e9fca310b5f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 40V, Positive-QTOF	splash10-0abi-0090000000-c1f0b82710fe7cf4a4fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 50V, Positive-QTOF	splash10-0a4l-0390000000-47a96f38cc39db4215d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aflatoxin B2 40V, Positive-QTOF	splash10-0abi-0090000000-f0166b802bbb8d10da36	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 10V, Positive-QTOF	splash10-014i-0039000000-d446a0adf08fa67d4d10	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 20V, Positive-QTOF	splash10-014i-0094000000-7a6e82836edee1f981c1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 40V, Positive-QTOF	splash10-02t9-1490000000-29ed28bb149ea2411c26	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 10V, Negative-QTOF	splash10-03di-0039000000-baac6939881949076644	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 20V, Negative-QTOF	splash10-03di-1097000000-d8269f211e11ae5c68b8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 40V, Negative-QTOF	splash10-0fb9-2190000000-9ea1e85b37f388c7c5e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 10V, Negative-QTOF	splash10-03di-0009000000-7c7169b7540bc9455826	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 20V, Negative-QTOF	splash10-03di-0049000000-5b4008ed9ce6ec916cef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 40V, Negative-QTOF	splash10-0002-0492000000-e1dbbfaed1432ac0341f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 10V, Positive-QTOF	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 20V, Positive-QTOF	splash10-014i-0019000000-519c5d1d27095e3ff42b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B2 40V, Positive-QTOF	splash10-000i-0091000000-6cb76c17d0d87928e540	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23648

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1216371

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 B2 (HMDB0035208)

MOL for HMDB0035208 (Aflatoxin B2)

3D MOL for HMDB0035208 (Aflatoxin B2)

3D SDF for HMDB0035208 (Aflatoxin B2)

3D-SDF for HMDB0035208 (Aflatoxin B2)

PDB for HMDB0035208 (Aflatoxin B2)

3D PDB for HMDB0035208 (Aflatoxin B2)

SMILES for HMDB0035208 (Aflatoxin B2)

INCHI for HMDB0035208 (Aflatoxin B2)

Structure for HMDB0035208 (Aflatoxin B2)

3D Structure for HMDB0035208 (Aflatoxin B2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra