MiMeDB: Showing metabocard for Aflatoxin B1 (MMDBc0048272)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:55:27 UTC

Update Date

2024-10-06 22:13:49 UTC

Metabolite ID

MMDBc0048272

Metabolite Identification

Common Name

Aflatoxin B1

Description

Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favourable for its growth. Favourable conditions include high moisture content (at least 7%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage (PMID: 17214555 ). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut).

Structure

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

 
  Mrv1652307191923442D          

 25 29  0  0  1  0            999 V2000
   22.2427  -19.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9571  -19.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4594  -19.7087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2806  -20.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6681  -19.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9606  -18.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9693  -20.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.9726  -19.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9571  -21.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4525  -21.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3860  -19.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6681  -20.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6785  -18.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1789  -20.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1824  -19.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3894  -18.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1661  -19.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3860  -21.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6716  -17.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1730  -18.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6526  -19.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0970  -20.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4317  -17.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8726  -18.9930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5560  -21.0975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  2  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  2  0  0  0  0
  7 10  1  0  0  0  0
  9 12  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 20 21  1  0  0  0  0
  3 24  1  6  0  0  0
  7 25  1  6  0  0  0
M  END

HMDB0006552
     RDKit          3D
Aflatoxin B1
 35 39  0  0  0  0  0  0  0  0999 V2000
   -1.5806    3.5811    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205    2.2082    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    1.4591   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    2.0104   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    1.2044   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199   -0.1518   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -0.7186   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4216   -2.0068   -0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7744   -2.5657   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -3.7941   -0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -1.8152   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209   -0.4529   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    0.0968   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366    0.1431    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9449   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3053   -2.1816   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826   -3.3288   -0.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327   -0.7748   -0.7277 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3938   -1.8129    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -1.3018    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    0.0239    0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.3442   -0.3291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3022    1.5227   -0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599    3.8839    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078    4.0988   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5717    3.9348   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410    3.0648    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0118   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664    0.4570    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896   -0.7867   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0009   -0.9813    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.1256   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253   -2.8302    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832   -1.8604    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661    0.3892   -1.0007 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  2  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  6
 19 33  1  0
 20 34  1  0
 22 35  1  6
M  END

 
  Mrv1652307191923442D          

 25 29  0  0  1  0            999 V2000
   22.2427  -19.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9571  -19.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4594  -19.7087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2806  -20.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6681  -19.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9606  -18.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9693  -20.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.9726  -19.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9571  -21.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4525  -21.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3860  -19.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6681  -20.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6785  -18.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1789  -20.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1824  -19.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3894  -18.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1661  -19.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3860  -21.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6716  -17.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1730  -18.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6526  -19.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0970  -20.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4317  -17.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8726  -18.9930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5560  -21.0975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  2  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  2  0  0  0  0
  7 10  1  0  0  0  0
  9 12  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 20 21  1  0  0  0  0
  3 24  1  6  0  0  0
  7 25  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048272

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12OC=C[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/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/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1

> <INCHI_KEY>
OQIQSTLJSLGHID-WNWIJWBNSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.135232034841625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.5843809030000005

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.787312891010785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4404302662976205

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
78.5851

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006552
     RDKit          3D
Aflatoxin B1
 35 39  0  0  0  0  0  0  0  0999 V2000
   -1.5806    3.5811    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205    2.2082    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    1.4591   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    2.0104   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    1.2044   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199   -0.1518   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -0.7186   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4216   -2.0068   -0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7744   -2.5657   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -3.7941   -0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -1.8152   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209   -0.4529   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    0.0968   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366    0.1431    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9449   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3053   -2.1816   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826   -3.3288   -0.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327   -0.7748   -0.7277 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3938   -1.8129    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -1.3018    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    0.0239    0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.3442   -0.3291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3022    1.5227   -0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599    3.8839    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078    4.0988   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5717    3.9348   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410    3.0648    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0118   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664    0.4570    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896   -0.7867   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0009   -0.9813    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.1256   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253   -2.8302    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832   -1.8604    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661    0.3892   -1.0007 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  2  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  6
 19 33  1  0
 20 34  1  0
 22 35  1  6
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0      41.520 -37.279   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      42.853 -36.512   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      40.057 -36.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      41.590 -38.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.180 -37.286   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      42.860 -34.973   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      39.143 -38.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.149 -35.527   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.853 -39.592   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      40.045 -39.296   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      45.521 -36.525   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.180 -38.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      44.200 -34.213   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      37.667 -37.556   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      37.674 -36.004   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.527 -34.986   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      46.977 -37.009   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      45.521 -39.592   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      44.187 -32.666   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      46.990 -34.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      47.885 -35.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.848 -38.806   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      47.473 -33.053   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      40.829 -35.454   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      38.371 -39.382   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8   24                                             
CONECT    4    1    9   10                                                  
CONECT    5    2   11   12                                                  
CONECT    6    2   13                                                       
CONECT    7    3   14   10   25                                             
CONECT    8    3   15                                                       
CONECT    9    4   12                                                       
CONECT   10    4    7                                                       
CONECT   11    5   16   17                                                  
CONECT   12    5   18    9                                                  
CONECT   13    6   19   16                                                  
CONECT   14    7   15                                                       
CONECT   15    8   14                                                       
CONECT   16   11   20   13                                                  
CONECT   17   11   21                                                       
CONECT   18   12   22                                                       
CONECT   19   13                                                            
CONECT   20   16   23   21                                                  
CONECT   21   17   20                                                       
CONECT   22   18                                                            
CONECT   23   20                                                            
CONECT   24    3                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0006552
HETATM    1  C1  UNL     1      -1.581   3.581   0.397  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.521   2.208   0.190  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.404   1.459  -0.035  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.854   2.010  -0.085  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.966   1.204  -0.318  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.820  -0.152  -0.501  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.558  -0.719  -0.453  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.422  -2.007  -0.627  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.774  -2.566  -0.585  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.892  -3.794  -0.753  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.907  -1.815  -0.358  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.821  -0.453  -0.168  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.546   0.097  -0.220  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.137   0.143   0.056  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.111  -0.945  -0.317  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.305  -2.182  -0.267  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.783  -3.329  -0.163  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.133  -0.775  -0.728  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.394  -1.813   0.310  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.153  -1.302   1.266  1.00  0.00           C  
HETATM   21  O5  UNL     1       4.446   0.024   0.977  1.00  0.00           O  
HETATM   22  C17 UNL     1       4.072   0.344  -0.329  1.00  0.00           C  
HETATM   23  O6  UNL     1       3.302   1.523  -0.410  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.560   3.884   1.464  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.808   4.099  -0.212  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.572   3.935  -0.013  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.941   3.065   0.060  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.367   1.012  -0.592  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.266   0.457   1.123  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.490  -0.787  -1.367  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.001  -0.981   0.327  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.307  -1.126  -1.747  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.025  -2.830   0.296  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.483  -1.860   2.138  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.966   0.389  -1.001  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   20   33
CONECT   20   21   34
CONECT   21   22
CONECT   22   23   35
END

HMDB0006552
     RDKit          3D
Aflatoxin B1
 35 39  0  0  0  0  0  0  0  0999 V2000
   -1.5806    3.5811    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205    2.2082    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    1.4591   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    2.0104   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    1.2044   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199   -0.1518   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -0.7186   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4216   -2.0068   -0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7744   -2.5657   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -3.7941   -0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -1.8152   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209   -0.4529   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    0.0968   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366    0.1431    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107   -0.9449   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3053   -2.1816   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826   -3.3288   -0.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327   -0.7748   -0.7277 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3938   -1.8129    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -1.3018    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    0.0239    0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.3442   -0.3291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3022    1.5227   -0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599    3.8839    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078    4.0988   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5717    3.9348   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410    3.0648    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0118   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664    0.4570    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896   -0.7867   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0009   -0.9813    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.1256   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253   -2.8302    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4832   -1.8604    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661    0.3892   -1.0007 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  2  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  6
 19 33  1  0
 20 34  1  0
 22 35  1  6
M  END

Synonyms

Value	Source
2,3,6Aalpha,9aalpha-tetrahydro-4-methoxycyclopenta(c)furo(3',2':4,5)furo(2,3-H)(1)benzopyran-1,11-dione	ChEBI
Aflatoxin b1 dihydrochloride, (6ar-cis)-isomer	HMDB
Aflatoxin b1, (6ar-cis)-isomer, 14C-labeled	HMDB
Aflatoxin b1, (6ar-cis)-isomer, 2H-labeled	HMDB
Aflatoxin b1, cis(+,-)-isomer	HMDB
Aflatoxin b	HMDB
HSDB 3453	HMDB
Aflatoxin b1, (6ar-cis)-isomer, 3H-labeled	HMDB
HSDB-3453	HMDB
(-)-Aflatoxin b1	HMDB
AFB1	HMDB
Aflatoxin B1	HMDB

Molecular Formula

C₁₇H₁₂O₆

Average Mass

312.2736

Monoisotopic Mass

312.063388116

IUPAC Name

(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

Traditional Name

(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

CAS Registry Number

1162-65-8

SMILES

[H][C@]12OC=C[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O

InChI Identifier

InChI=1S/C17H12O6/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/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:2504 )
aflatoxin (CHEBI:2504 )
aromatic ketone (CHEBI:2504 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	1.73	ALOGPS
logP	1.58	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-4.4	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	78.59 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0098000000-ddc3fa0269c995f2f419	2019-06-20	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0098000000-ddc3fa0269c995f2f419	2019-06-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0aor-0039000000-2a3e295d237d548522c8	2019-06-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-0d18d76abea2df4bc5e0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02u3-3191000000-be180eeffb213d24d9aa	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0029000000-d57aa65f4120350bede2	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-082i-0091000000-ed39f380b022171d7935	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03fr-7894000000-57075e5f64c138201081	2019-06-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193871	Aflatoxin B1 aldehyde reductase member 2	Enzyme	O43488	Homo sapiens
MMDBp0195888	Aflatoxin B1 aldehyde reductase member 3	Enzyme	O95154	Homo sapiens
MMDBp0195889	Aflatoxin B1 aldehyde reductase member 4	Enzyme	Q8NHP1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001871	Aflatoxin B1	2,3-Epoxyaflatoxin B1	cytochrome P450, family 3, subfamily A, polypeptide 5	VMH	15579107
MMDBr0010477	Aflatoxin B1	Aflatoxin Q1	cytochrome P450, family 1, subfamily A, polypeptide 1	VMH; KEGG	30371894
MMDBr0010478	Aflatoxin B1	Aflatoxin M1	cytochrome P450, family 1, subfamily A, polypeptide 2	VMH; KEGG	30371894
MMDBr0010480	Aflatoxin B1	Aflatoxin B1-Endo-8,9-Epoxide	cytochrome P450, family 1, subfamily A, polypeptide 2	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Reye's syndrome	Increased	Association	Human Blood	HMDB	6420055

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	6	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.009		0.008	0.014	uM	Adult (>18 years old)	Both	Reye's Syndrome	HMDB	6420055
Human Blood	Detected and Quantified	0.0009	0.00097			uM	Adult (>18 years old)	Both	Normal	HMDB	6420055

External Links

HMDB ID

HMDB0006552

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Aflatoxin

METLIN ID

Not Available

PubChem Compound

186907

PDB ID

Not Available

ChEBI ID

2504

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Amici M, Cecarini V, Pettinari A, Bonfili L, Angeletti M, Barocci S, Biagetti M, Fioretti E, Eleuteri AM: Binding of aflatoxins to the 20S proteasome: effects on enzyme functionality and implications for oxidative stress and apoptosis. Biol Chem. 2007 Jan;388(1):107-17. doi: 10.1515/BC.2007.012. [PubMed:17214555 ]

Showing metabocard for Aflatoxin B1 (MMDBc0048272)

MOL for #<Metabolite:0x0000559d053038e0>

3D MOL for #<Metabolite:0x0000559d053038e0>

3D SDF for #<Metabolite:0x0000559d053038e0>

3D-SDF for #<Metabolite:0x0000559d053038e0>

PDB for #<Metabolite:0x0000559d053038e0>

3D PDB for #<Metabolite:0x0000559d053038e0>

SMILES for #<Metabolite:0x0000559d053038e0>

INCHI for #<Metabolite:0x0000559d053038e0>

Structure for #<Metabolite:0x0000559d053038e0>

3D Structure for #<Metabolite:0x0000559d053038e0>