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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:03 UTC

Update Date

2022-03-07 02:52:34 UTC

HMDB ID

HMDB0030479

Secondary Accession Numbers

HMDB30479

Metabolite Identification

Common Name

Aflatoxin M1

Description

Aflatoxin G belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone ring fused to the coumarin moiety of the difurocoumarin skeleton. Aflatoxin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxin G is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. A broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin G belongs to the family of Difurocoumarolactone Series.

Structure

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


  Mrv0541 02241220332D          

 25 29  0  0  0  0            999 V2000
    2.0625   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -1.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.7384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5634   -1.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0259   -0.3877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -2.4183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
 13  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  9  1  0  0  0  0
  1  4  2  0  0  0  0
  6  1  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  1  0  0  0  0
  8  9  2  0  0  0  0
 18 12  1  0  0  0  0
 12 13  1  0  0  0  0
 19 14  1  0  0  0  0
 14 13  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 21  1  6  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 24  2  0  0  0  0
  7 25  2  0  0  0  0
M  END

HMDB0030479
     RDKit          3D
Aflatoxin M1
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.7236    3.5746   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    2.1655   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    1.4049   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    1.9751   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    1.2396   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.1442   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.7450   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -2.0525   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -2.6804    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -3.9283    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -1.9710    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9531   -0.5998    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    0.0210   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.0389    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2062   -1.1807    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3886   -2.3892    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -3.5702    0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -0.6814   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0996   -1.7670   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6554   -0.9022    0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.2086    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186    0.5124   -0.1963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    0.5103   -0.9587 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0427    1.6319   -0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017    4.0242    0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    3.8775   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841    3.9181    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    3.0634   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.3762   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3921    0.7661    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.1593    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.2427   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427   -2.5199   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833   -1.5378    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.1912    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902    0.4494   -2.0372 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  6
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  6
M  END


  Mrv0541 02241220332D          

 25 29  0  0  0  0            999 V2000
    2.0625   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -1.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.7384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5634   -1.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0259   -0.3877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -2.4183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
 13  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  9  1  0  0  0  0
  1  4  2  0  0  0  0
  6  1  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  1  0  0  0  0
  8  9  2  0  0  0  0
 18 12  1  0  0  0  0
 12 13  1  0  0  0  0
 19 14  1  0  0  0  0
 14 13  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 21  1  6  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 24  2  0  0  0  0
  7 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030479

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/s1

> <INCHI_KEY>
MJBWDEQAUQTVKK-IAGOWNOFSA-N

> <FORMULA>
C17H12O7

> <MOLECULAR_WEIGHT>
328.273

> <EXACT_MASS>
328.058302738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.066973528593742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.9292005210000003

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.78919879223179

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.424946112265848

> <JCHEM_PKA_STRONGEST_BASIC>
-4.362528487221817

> <JCHEM_POLAR_SURFACE_AREA>
91.28999999999999

> <JCHEM_REFRACTIVITY>
79.673

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030479
     RDKit          3D
Aflatoxin M1
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.7236    3.5746   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    2.1655   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    1.4049   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    1.9751   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    1.2396   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.1442   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.7450   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -2.0525   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -2.6804    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -3.9283    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -1.9710    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9531   -0.5998    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    0.0210   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.0389    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2062   -1.1807    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3886   -2.3892    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -3.5702    0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -0.6814   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0996   -1.7670   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6554   -0.9022    0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.2086    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186    0.5124   -0.1963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    0.5103   -0.9587 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0427    1.6319   -0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017    4.0242    0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    3.8775   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841    3.9181    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    3.0634   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.3762   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3921    0.7661    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.1593    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.2427   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427   -2.5199   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833   -1.5378    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.1912    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902    0.4494   -2.0372 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  6
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  6
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       3.850  -1.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -4.785   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -2.475   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184   0.605   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850  -0.165   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.851   0.605   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.517  -0.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.517  -1.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.185  -1.705   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.185  -0.165   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.052  -4.491   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.516  -4.015   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.516  -2.475   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.016  -0.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.422  -1.309   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.341  -2.846   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.147  -3.245   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.052  -1.999   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.915  -0.724   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -0.726  -4.514   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0       6.517  -4.785   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.851  -4.015   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.184   2.145   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.851   2.145   0.000  0.00  0.00           O+0
CONECT    1   14    4    6                                                  
CONECT    2   13    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    9    1                                                  
CONECT    5    6    8   24                                                  
CONECT    6    1    5                                                       
CONECT    7    8   11   25                                                  
CONECT    8    5    7    9                                                  
CONECT    9    4   10    8                                                  
CONECT   10   11    9                                                       
CONECT   11   10    7                                                       
CONECT   12   18   13                                                       
CONECT   13    2   12   14                                                  
CONECT   14    1   19   13                                                  
CONECT   15   16   19                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   12   17   19   21                                             
CONECT   19   14   15   18   20                                             
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22    3   23                                                       
CONECT   23   22                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0030479
HETATM    1  C1  UNL     1      -1.724   3.575  -0.167  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.808   2.165  -0.070  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.670   1.405  -0.150  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.583   1.975  -0.326  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.726   1.240  -0.409  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.645  -0.144  -0.313  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.421  -0.745  -0.138  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.328  -2.052  -0.046  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.815  -2.680   0.122  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.879  -3.928   0.207  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.004  -1.971   0.211  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.953  -0.600   0.120  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.737   0.021  -0.056  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.321  -0.039   0.238  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.206  -1.181   0.629  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.389  -2.389   0.393  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.832  -3.570   0.358  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.026  -0.681  -0.435  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.100  -1.767  -1.269  1.00  0.00           O  
HETATM   20  C15 UNL     1       3.655  -0.902   0.891  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.763  -0.209   0.960  1.00  0.00           C  
HETATM   22  O6  UNL     1       5.019   0.512  -0.196  1.00  0.00           O  
HETATM   23  C17 UNL     1       3.804   0.510  -0.959  1.00  0.00           C  
HETATM   24  O7  UNL     1       3.043   1.632  -0.581  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.702   4.024   0.098  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.386   3.877  -1.183  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.984   3.918   0.592  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.654   3.063  -0.403  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.661   0.376  -0.751  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.392   0.766   0.992  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.517  -1.159   1.684  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.132  -1.243  -0.002  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.643  -2.520  -0.838  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.283  -1.538   1.710  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.428  -0.191   1.838  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.990   0.449  -2.037  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   18
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   14
CONECT   14   15   29   30
CONECT   15   16   31   32
CONECT   16   17   17
CONECT   18   19   20   23
CONECT   19   33
CONECT   20   21   21   34
CONECT   21   22   35
CONECT   22   23
CONECT   23   24   36
END

HMDB0030479
     RDKit          3D
Aflatoxin M1
 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.7236    3.5746   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    2.1655   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    1.4049   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    1.9751   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    1.2396   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.1442   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.7450   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -2.0525   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -2.6804    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -3.9283    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -1.9710    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9531   -0.5998    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    0.0210   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.0389    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2062   -1.1807    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3886   -2.3892    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -3.5702    0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -0.6814   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0996   -1.7670   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6554   -0.9022    0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.2086    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186    0.5124   -0.1963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    0.5103   -0.9587 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0427    1.6319   -0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017    4.0242    0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    3.8775   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841    3.9181    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    3.0634   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.3762   -0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3921    0.7661    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.1593    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.2427   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427   -2.5199   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833   -1.5378    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.1912    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902    0.4494   -2.0372 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  6
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 13  3  1  0
 23 18  1  0
 24  5  1  0
 13  7  2  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aflatoxin g1	HMDB
4-Hydroxyaflatoxin b1	ChEBI
AFM1	ChEBI
4 Hydroxyaflatoxin b1	MeSH
Aflatoxin m1, cis(+-)-isomer	MeSH
Aflatoxin m	MeSH

Chemical Formula

C₁₇H₁₂O₇

Average Molecular Weight

328.273

Monoisotopic Molecular Weight

328.058302738

IUPAC Name

(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

Traditional Name

(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione

CAS Registry Number

6795-23-9

SMILES

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

InChI Identifier

InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/s1

InChI Key

MJBWDEQAUQTVKK-IAGOWNOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone 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

Difurocoumarolactones

Alternative Parents

Substituents

Difurocoumarolactone
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Dihydrofuran
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a secondary metabolite (CPD-10178 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030479)
Cytoplasm (HMDB: HMDB0030479)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030479)

Source

Endogenous

Endogenous (HMDB: HMDB0030479)

Plant

Plant (HMDB: HMDB0030479)

Animal

Animal (HMDB: HMDB0030479)

Fungi

Aspergillus flavus (HMDB: HMDB0030479)
Aspergillus parasiticus (HMDB: HMDB0030479)

Exogenous

Food

Food (HMDB: HMDB0030479)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Biological role

human xenobiotic metabolite (HMDB: HMDB0030479)
fungal metabolite (HMDB: HMDB0030479)
mammalian metabolite (HMDB: HMDB0030479)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	299 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.99 g/L	ALOGPS
logP	1.21	ALOGPS
logP	0.93	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.67 m³·mol⁻¹	ChemAxon
Polarizability	31.07 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]+	172.175	31661259
DarkChem	[M-H]-	171.827	31661259
DeepCCS	[M-2H]-	202.843	30932474
DeepCCS	[M+Na]+	177.693	30932474
AllCCS	[M+H]+	173.3	32859911
AllCCS	[M+H-H2O]+	169.9	32859911
AllCCS	[M+NH4]+	176.4	32859911
AllCCS	[M+Na]+	177.2	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	176.7	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin M1	[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O	4181.7	Standard polar	33892256
Aflatoxin M1	[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O	2816.1	Standard non polar	33892256
Aflatoxin M1	[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O	2992.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aflatoxin M1,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@]1(O[Si](C)(C)C)C=CO[C@@H]1O2	2959.0	Semi standard non polar	33892256
Aflatoxin M1,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@]1(O[Si](C)(C)C(C)(C)C)C=CO[C@@H]1O2	3169.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin M1 GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-1093000000-d4b028c14eb0b56a6dab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin M1 GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-3019000000-16e7ca1f490d12f2251c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aflatoxin M1 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 M1 10V, Positive-QTOF	splash10-004i-0019000000-bbac981b86ec0492f21d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Positive-QTOF	splash10-01t9-0049000000-6f31a5efa1e5ce49dc2e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Positive-QTOF	splash10-03fs-4590000000-05fb74b57fa5ff2e34e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Negative-QTOF	splash10-004i-0029000000-391e040bf68fd12a6ee3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Negative-QTOF	splash10-004i-0029000000-8af815da6e7ffdd1aa66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Negative-QTOF	splash10-01td-4490000000-718acd1824f6a41573d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Negative-QTOF	splash10-004i-0009000000-3eb691afb29ed57b3f5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Negative-QTOF	splash10-004i-0019000000-378c0fff332dffa4ac83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Negative-QTOF	splash10-004j-1393000000-72a0612864b183b85440	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Positive-QTOF	splash10-004i-0009000000-a6e8d4715f87e5602d4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Positive-QTOF	splash10-004i-0009000000-60957124411bf6b33980	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Positive-QTOF	splash10-0fbi-0079000000-fe971dd41bcdbd5a26bd	2021-09-22	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

14421

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Aflatoxin M1 (HMDB0030479)

MOL for HMDB0030479 (Aflatoxin M1)

3D MOL for HMDB0030479 (Aflatoxin M1)

3D SDF for HMDB0030479 (Aflatoxin M1)

3D-SDF for HMDB0030479 (Aflatoxin M1)

PDB for HMDB0030479 (Aflatoxin M1)

3D PDB for HMDB0030479 (Aflatoxin M1)

SMILES for HMDB0030479 (Aflatoxin M1)

INCHI for HMDB0030479 (Aflatoxin M1)

Structure for HMDB0030479 (Aflatoxin M1)

3D Structure for HMDB0030479 (Aflatoxin M1)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra