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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-02-04 09:42:06 UTC

Update Date

2021-09-14 15:47:34 UTC

HMDB ID

HMDB0011672

Secondary Accession Numbers

HMDB11672

Metabolite Identification

Common Name

Aflatoxin B1 dialcohol

Description

Aflatoxin B1 dialcohol is an aflatoxin B1 metabolite. Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, most notably Aspergillus flavus and Aspergillus parasiticus. 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 favorable for its growth. Favorable 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). Aflatoxin B1 dialcohol is a derivative of aflatoxin B1 (AFB1) that is formed from AFB1-dihydrodiol (AFB1-dhd) by a novel aldehyde reductase (Aflatoxin B1 aldehyde reductase) (PMID: 1134261 ). Aflatoxin B1 aldehyde reductases (AFARs) are inducible members of the aldo-keto reductase superfamily. They convert aflatoxin B1 dialdehyde derived from the exo- and endo-8,9-epoxides into a number of reduced alcohol products that might be less capable of forming covalent adducts with proteins (PMID: 18266327 ). AFB1 dialdehyde does not bind to DNA but can react with protein lysine groups. There are two principal techniques that can be used to detect levels of aflatoxin in humans. One measures the AFB1-guanine adduct in the urine of subjects. The presence of this breakdown product indicates exposure to aflatoxin B1 in the past 24 hours. The second technique involves the measurement of the AFB1-albumin adduct level in the blood serum.

Structure

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

HMDB0011672
     RDKit          3D
Aflatoxin B1 dialcohol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.3436    3.6952    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    2.3099    0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816    1.5747   -0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    2.2201   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    1.5059   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.1398   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.4921   -0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    0.2056   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -0.4775   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814   -1.8118   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -2.3410    0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -3.5276    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -1.2184    0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -0.0184    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -2.4447   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262   -3.4380   -1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0491   -1.9613   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.3194   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7009    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    0.3889    1.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -1.3278    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -0.3824   -0.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158    0.9428   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437    1.9294   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    4.2505   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4156    4.0103    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017    3.9991    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    3.2960   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6165   -1.2505    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -1.2075    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0007    0.8911    0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112    0.0212   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -2.2828   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -2.4440    0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871   -1.1503   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838   -1.4558    0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151    0.2359    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478   -2.2497   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8709   -1.5781    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    0.3837    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876    1.0831   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938    0.9966   -1.5803 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
  8  3  1  0
 14  9  1  0
 24  5  1  0
 17  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
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 17 33  1  0
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 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END


  Mrv0541 02241201502D          

 24 27  0  0  0  0            999 V2000
   15.9081   -6.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4602   -5.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3206   -6.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2138   -5.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1276   -6.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0831   -6.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6706   -6.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9081   -7.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0831   -7.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2886   -4.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6706   -5.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3206   -8.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9081   -8.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6706   -8.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0831   -8.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1456   -8.2711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5581   -8.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5311   -9.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8637   -8.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2506   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4660   -8.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8529   -7.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4221   -7.0836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7775   -9.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  3  1  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  2  0  0  0  0
 11  6  2  0  0  0  0
 12  8  1  0  0  0  0
  9  8  2  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 14  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 24 19  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011672

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(CO2)C(O)CO)C2=C1C1=C(C(=O)CC1)C(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-23-14-5-15-17(10(7-24-15)13(22)6-19)9-4-12(21)18-8(16(9)14)2-3-11(18)20/h5,10,13,19,22H,2-4,6-7H2,1H3

> <INCHI_KEY>
QEIDPNWKOZPLQZ-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.61133151662429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1,2-dihydroxyethyl)-8-methoxy-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadeca-1(9),2(6),7,10(14)-tetraene-13,15-dione

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.3993722513333331

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.016597103787728

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.853784519584291

> <JCHEM_PKA_STRONGEST_BASIC>
-2.946488276100178

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
85.906

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(1,2-dihydroxyethyl)-8-methoxy-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadeca-1(9),2(6),7,10(14)-tetraene-13,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011672
     RDKit          3D
Aflatoxin B1 dialcohol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.3436    3.6952    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    2.3099    0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816    1.5747   -0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    2.2201   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    1.5059   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.1398   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.4921   -0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    0.2056   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -0.4775   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814   -1.8118   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -2.3410    0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -3.5276    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -1.2184    0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -0.0184    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -2.4447   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262   -3.4380   -1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0491   -1.9613   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.3194   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7009    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    0.3889    1.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -1.3278    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -0.3824   -0.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158    0.9428   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437    1.9294   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    4.2505   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4156    4.0103    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017    3.9991    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    3.2960   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6165   -1.2505    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -1.2075    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0007    0.8911    0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112    0.0212   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -2.2828   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -2.4440    0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871   -1.1503   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838   -1.4558    0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151    0.2359    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478   -2.2497   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8709   -1.5781    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    0.3837    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876    1.0831   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938    0.9966   -1.5803 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
  8  3  1  0
 14  9  1  0
 24  5  1  0
 17  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      29.695 -11.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.726 -10.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.465 -12.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.132 -10.920   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.972 -12.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.155 -11.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.385 -12.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.695 -14.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.155 -14.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      30.405  -8.788   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.385 -10.105   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      30.465 -15.439   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.695 -16.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.385 -15.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.155 -16.773   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      32.005 -15.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      32.775 -16.773   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      27.125 -17.917   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      25.879 -15.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.734 -14.729   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.270 -15.205   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      22.125 -14.175   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      25.055 -13.223   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      25.718 -17.291   0.000  0.00  0.00           C+0
CONECT    1    2    6    3                                                  
CONECT    2    1    4   10                                                  
CONECT    3    5    1    8                                                  
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
CONECT    6    1    7   11                                                  
CONECT    7    6    9                                                       
CONECT    8    3   12    9                                                  
CONECT    9    7    8   14                                                  
CONECT   10    2                                                            
CONECT   11    6                                                            
CONECT   12    8   13   16                                                  
CONECT   13   12   15                                                       
CONECT   14    9   15   19                                                  
CONECT   15   13   14   18                                                  
CONECT   16   12   17                                                       
CONECT   17   16                                                            
CONECT   18   15   24                                                       
CONECT   19   14   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0011672
HETATM    1  C1  UNL     1      -2.344   3.695   0.336  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.315   2.310   0.172  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.182   1.575  -0.091  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.055   2.220  -0.212  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.209   1.506  -0.476  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.150   0.140  -0.624  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.077  -0.492  -0.504  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.251   0.206  -0.239  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.547  -0.477  -0.129  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.581  -1.812  -0.294  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.853  -2.341   0.213  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.251  -3.528   0.048  1.00  0.00           O  
HETATM   13  C11 UNL     1      -4.515  -1.218   0.921  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.940  -0.018   0.148  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.421  -2.445  -0.915  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.626  -3.438  -1.687  1.00  0.00           O  
HETATM   17  C14 UNL     1      -0.049  -1.961  -0.666  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.556  -0.319  -0.898  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.192  -0.701   0.405  1.00  0.00           C  
HETATM   20  O4  UNL     1       3.227   0.389   1.270  1.00  0.00           O  
HETATM   21  C17 UNL     1       4.553  -1.328   0.272  1.00  0.00           C  
HETATM   22  O5  UNL     1       5.446  -0.382  -0.220  1.00  0.00           O  
HETATM   23  C18 UNL     1       3.116   0.943  -1.511  1.00  0.00           C  
HETATM   24  O6  UNL     1       2.544   1.929  -0.638  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.875   4.250  -0.500  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.416   4.010   0.388  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.902   3.999   1.311  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.081   3.296  -0.091  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.617  -1.250   0.824  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.152  -1.208   1.952  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.001   0.891   0.739  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.511   0.021  -0.802  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.599  -2.283  -1.505  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.294  -2.444   0.274  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.587  -1.150  -1.612  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.484  -1.456   0.880  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.715   0.236   2.098  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.548  -2.250  -0.324  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.871  -1.578   1.324  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.418   0.384   0.410  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.588   1.083  -2.477  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.194   0.997  -1.580  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   18
CONECT    7    8    8   17
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   15
CONECT   11   12   12   13
CONECT   13   14   29   30
CONECT   14   31   32
CONECT   15   16   16   17
CONECT   17   33   34
CONECT   18   19   23   35
CONECT   19   20   21   36
CONECT   20   37
CONECT   21   22   38   39
CONECT   22   40
CONECT   23   24   41   42
END

HMDB0011672
     RDKit          3D
Aflatoxin B1 dialcohol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.3436    3.6952    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    2.3099    0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816    1.5747   -0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    2.2201   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    1.5059   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.1398   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.4921   -0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    0.2056   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -0.4775   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814   -1.8118   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -2.3410    0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -3.5276    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -1.2184    0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -0.0184    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -2.4447   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262   -3.4380   -1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0491   -1.9613   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.3194   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7009    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    0.3889    1.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -1.3278    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -0.3824   -0.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158    0.9428   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437    1.9294   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    4.2505   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4156    4.0103    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017    3.9991    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    3.2960   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6165   -1.2505    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -1.2075    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0007    0.8911    0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112    0.0212   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -2.2828   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -2.4440    0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871   -1.1503   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838   -1.4558    0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151    0.2359    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478   -2.2497   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8709   -1.5781    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    0.3837    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876    1.0831   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938    0.9966   -1.5803 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
  8  3  1  0
 14  9  1  0
 24  5  1  0
 17  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxyphenylpyruvate	Generator
3-HPPA	HMDB
HPPA	HMDB
m-Hydroxyphenylpyruvate	HMDB
m-Hydroxyphenylpyruvic acid	HMDB
AFB1 dialcohol	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

3-(1,2-dihydroxyethyl)-8-methoxy-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadeca-1(9),2(6),7,10(14)-tetraene-13,15-dione

Traditional Name

3-(1,2-dihydroxyethyl)-8-methoxy-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadeca-1(9),2(6),7,10(14)-tetraene-13,15-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(CO2)C(O)CO)C2=C1C1=C(C(=O)CC1)C(=O)C2

InChI Identifier

InChI=1S/C18H18O6/c1-23-14-5-15-17(10(7-24-15)13(22)6-19)9-4-12(21)18-8(16(9)14)2-3-11(18)20/h5,10,13,19,22H,2-4,6-7H2,1H3

InChI Key

QEIDPNWKOZPLQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Phenylpyruvate
3-phenylpropanoic-acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-keto acid
Keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0011672)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.91 m³·mol⁻¹	ChemAxon
Polarizability	33.61 Å³	ChemAxon
Number of Rings	4	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]+	178.181	31661259
DarkChem	[M-H]-	171.631	31661259
DeepCCS	[M+H]+	178.368	30932474
DeepCCS	[M-H]-	176.01	30932474
DeepCCS	[M-2H]-	209.978	30932474
DeepCCS	[M+Na]+	185.205	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	179.1	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	180.3	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin B1 dialcohol	COC1=CC2=C(C(CO2)C(O)CO)C2=C1C1=C(C(=O)CC1)C(=O)C2	4720.3	Standard polar	33892256
Aflatoxin B1 dialcohol	COC1=CC2=C(C(CO2)C(O)CO)C2=C1C1=C(C(=O)CC1)C(=O)C2	2942.9	Standard non polar	33892256
Aflatoxin B1 dialcohol	COC1=CC2=C(C(CO2)C(O)CO)C2=C1C1=C(C(=O)CC1)C(=O)C2	3334.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin B1 dialcohol,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(CO)O[Si](C)(C)C)CO2	2973.5	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(O)CO[Si](C)(C)C)CO2	2992.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(O)CO)CO2	3009.0	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TMS,isomer #4	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO)CO2	3109.5	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	2996.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(CO)O[Si](C)(C)C)CO2	3021.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(CO)O[Si](C)(C)C)CO2	3089.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #4	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(O)CO[Si](C)(C)C)CO2	3026.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO[Si](C)(C)C)CO2	3108.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #6	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO)CO2	3128.0	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(=O)CCC4=C13)C(C(CO)O[Si](C)(C)C)CO2	3089.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TMS,isomer #8	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(=O)CCC4=C13)C(C(O)CO[Si](C)(C)C)CO2	3108.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	2998.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	2949.6	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C)=CC1)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3546.2	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3081.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3041.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3485.0	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO)O[Si](C)(C)C)CO2	3078.2	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO)O[Si](C)(C)C)CO2	2977.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO)O[Si](C)(C)C)CO2	3672.4	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3081.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3041.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3485.0	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO[Si](C)(C)C)CO2	3076.2	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO[Si](C)(C)C)CO2	2987.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(O)CO[Si](C)(C)C)CO2	3697.1	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C)CO2	3078.2	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C)CO2	2977.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C)CO2	3672.4	Standard polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C)CO2	3076.2	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C)CO2	2987.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C)CO2	3697.1	Standard polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3057.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	2987.0	Standard non polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C)=CC1)C(O[Si](C)(C)C)=C3)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3423.1	Standard polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3057.1	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	2987.0	Standard non polar	33892256
Aflatoxin B1 dialcohol,4TMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C)=C4C(O[Si](C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C)O[Si](C)(C)C)CO2	3423.1	Standard polar	33892256
Aflatoxin B1 dialcohol,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3201.7	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TBDMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3215.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TBDMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(O)CO)CO2	3232.3	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,1TBDMS,isomer #4	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO)CO2	3342.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3466.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3479.7	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3562.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #4	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3474.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3559.3	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #6	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO)CO2	3609.3	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)CCC4=C13)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3562.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,2TBDMS,isomer #8	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)CCC4=C13)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3559.3	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3683.9	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3495.1	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)C3)C(O[Si](C)(C)C(C)(C)C)=CC1)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3769.3	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3762.9	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3692.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #2	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3759.5	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3804.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3471.8	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #3	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3858.0	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3762.9	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3692.3	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #4	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3759.5	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3798.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3481.8	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #5	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3878.0	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3804.8	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3471.8	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #6	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO)O[Si](C)(C)C(C)(C)C)CO2	3858.0	Standard polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3798.4	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3481.8	Standard non polar	33892256
Aflatoxin B1 dialcohol,3TBDMS,isomer #7	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(O)CO[Si](C)(C)C(C)(C)C)CO2	3878.0	Standard polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3972.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3628.1	Standard non polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(O[Si](C)(C)C(C)(C)C)=CC1)C(O[Si](C)(C)C(C)(C)C)=C3)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3733.0	Standard polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3972.6	Semi standard non polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3628.1	Standard non polar	33892256
Aflatoxin B1 dialcohol,4TBDMS,isomer #2	COC1=CC2=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C4C(O[Si](C)(C)C(C)(C)C)=CCC4=C13)C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2	3733.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B1 dialcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0il1-3095000000-16ef5315b7ab6df146bc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B1 dialcohol GC-MS (2 TMS) - 70eV, Positive	splash10-05di-3101900000-c0f3af13cd96b13d1015	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin B1 dialcohol 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 B1 dialcohol 10V, Positive-QTOF	splash10-01q9-0039000000-d8a6984403c7ad8b5c01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 20V, Positive-QTOF	splash10-03ed-4094000000-5948fc0ff620c7856cc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 40V, Positive-QTOF	splash10-05o1-5190000000-a1f4683c20837362b917	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 10V, Negative-QTOF	splash10-004i-0029000000-77d4b6f4f9f8a6b2e52f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 20V, Negative-QTOF	splash10-02vj-1095000000-6762670b1cd34962f95a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 40V, Negative-QTOF	splash10-002f-2090000000-194a078730ef606ab2dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 10V, Positive-QTOF	splash10-01q9-0059000000-c32795aa45a9bcef9681	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 20V, Positive-QTOF	splash10-01q9-0059000000-5f5d5c2f0688199f5ad9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 40V, Positive-QTOF	splash10-0udl-0095000000-087e1cea9acd8977b36a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 10V, Negative-QTOF	splash10-004i-0049000000-9a86ca58dcf438f3b2cc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 20V, Negative-QTOF	splash10-0gb9-0090000000-6f189f4bbe7fc2b09e64	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin B1 dialcohol 40V, Negative-QTOF	splash10-0fur-0091000000-9a41cedfbfb6cfb0672b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028354

KNApSAcK ID

Not Available

Chemspider ID

4476924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxyphenylpyruvic acid

METLIN ID

Not Available

PubChem Compound

5318321

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

Ragan CA Jr: Editorial: The great scourge of our society. Med Times. 1975 Jun;103(6):23, 29. [PubMed:1134261 ]
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. [PubMed:17214555 ]
Johnson DN, Egner PA, Obrian G, Glassbrook N, Roebuck BD, Sutter TR, Payne GA, Kensler TW, Groopman JD: Quantification of urinary aflatoxin B1 dialdehyde metabolites formed by aflatoxin aldehyde reductase using isotope dilution tandem mass spectrometry. Chem Res Toxicol. 2008 Mar;21(3):752-60. doi: 10.1021/tx700397n. Epub 2008 Feb 12. [PubMed:18266327 ]

Enzymes

Enzyme Details

1. Aflatoxin B1 aldehyde reductase member 2

General function:: Energy production and conversion
Specific function:: Catalyzes the NADPH-dependent reduction of succinic semialdehyde to gamma-hydroxybutyrate. May have an important role in producing the neuromodulator gamma-hydroxybutyrate (GHB). Has broad substrate specificity. Has NADPH-dependent aldehyde reductase activity towards 2-carboxybenzaldehyde, 2-nitrobenzaldehyde and pyridine-2-aldehyde (in vitro). Can reduce 1,2-naphthoquinone and 9,10-phenanthrenequinone (in vitro). Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen.
Gene Name:: AKR7A2
Uniprot ID:: O43488
Molecular weight:: 39588.65

Enzyme Details

2. Aflatoxin B1 aldehyde reductase member 3

General function:: Involved in oxidoreductase activity
Specific function:: Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen
Gene Name:: AKR7A3
Uniprot ID:: O95154
Molecular weight:: 37206.1

Enzyme Details

3. Aflatoxin B1 aldehyde reductase member 4

General function:: Involved in oxidoreductase activity
Specific function:: Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen
Gene Name:: AKR7L
Uniprot ID:: Q8NHP1
Molecular weight:: 36963.5

Showing metabocard for Aflatoxin B1 dialcohol (HMDB0011672)

MOL for HMDB0011672 (Aflatoxin B1 dialcohol)

3D MOL for HMDB0011672 (Aflatoxin B1 dialcohol)

3D SDF for HMDB0011672 (Aflatoxin B1 dialcohol)

3D-SDF for HMDB0011672 (Aflatoxin B1 dialcohol)

PDB for HMDB0011672 (Aflatoxin B1 dialcohol)

3D PDB for HMDB0011672 (Aflatoxin B1 dialcohol)

SMILES for HMDB0011672 (Aflatoxin B1 dialcohol)

INCHI for HMDB0011672 (Aflatoxin B1 dialcohol)

Structure for HMDB0011672 (Aflatoxin B1 dialcohol)

3D Structure for HMDB0011672 (Aflatoxin B1 dialcohol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes