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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:18 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030831

Secondary Accession Numbers

HMDB30831

Metabolite Identification

Common Name

Alternariol

Description

Alternariol, also known as AOH, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Alternariol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Alternariol.

Structure

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

HMDB0030831
     RDKit          3D
Alternariol
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.4383   -2.0732   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -0.6450    0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -0.1690    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467    1.1432    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7036    1.5255    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    2.0731    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.6757    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    2.5638    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    2.2970    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    3.1951    0.0490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    0.9865   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    0.6755   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338    1.7374   -0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6323   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4106   -1.6444   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -2.9557   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.3500   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.0455   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    0.3105    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.6268    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5170   -2.5251   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -2.4790   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749   -0.9281    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.5930    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    3.1251    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238    1.5904   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3941   -0.8141   -0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013   -3.4406   -1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4425   -2.1626   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv0541 09051416262D          

 19 21  0  0  0  0            999 V2000
    0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030831

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

> <INCHI_KEY>
CEBXXEKPIIDJHL-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.13868270042601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.1780528656666664

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.507964495567593

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.630330073955936

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0253299520481045

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
67.92300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alternariol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030831
     RDKit          3D
Alternariol
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.4383   -2.0732   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -0.6450    0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -0.1690    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467    1.1432    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7036    1.5255    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    2.0731    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.6757    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    2.5638    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    2.2970    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    3.1951    0.0490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    0.9865   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    0.6755   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338    1.7374   -0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6323   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4106   -1.6444   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -2.9557   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.3500   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.0455   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    0.3105    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.6268    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5170   -2.5251   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -2.4790   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749   -0.9281    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.5930    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    3.1251    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238    1.5904   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3941   -0.8141   -0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013   -3.4406   -1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4425   -2.1626   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.056  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.874   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.056   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.826   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.516   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.746   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.206   3.437   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.366   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.874   3.437   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.564   4.771   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.746   3.437   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    7                                                       
CONECT    3    8    9                                                       
CONECT    4    8   10                                                       
CONECT    5    7   11                                                       
CONECT    6    1    2   12                                                  
CONECT    7    2    5   15                                                  
CONECT    8    3    4   16                                                  
CONECT    9    3   12   13                                                  
CONECT   10    4   13   17                                                  
CONECT   11    5   12   19                                                  
CONECT   12    6    9   11                                                  
CONECT   13    9   10   14                                                  
CONECT   14   13   18   19                                                  
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0030831
HETATM    1  C1  UNL     1       1.438  -2.073  -0.066  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.667  -0.645   0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.994  -0.169   0.112  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.347   1.143   0.185  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.704   1.525   0.258  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.352   2.073   0.184  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.034   1.676   0.113  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.085   2.564   0.112  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.175   2.297   0.048  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.063   3.195   0.049  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.585   0.986  -0.024  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.924   0.675  -0.084  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.834   1.737  -0.079  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.334  -0.632  -0.148  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.411  -1.644  -0.151  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.857  -2.956  -0.215  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.039  -1.350  -0.090  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.657  -0.045  -0.029  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.693   0.310   0.040  1.00  0.00           C  
HETATM   20  H1  UNL     1       1.161  -2.627   0.850  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.517  -2.525  -0.139  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.122  -2.479  -1.054  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.775  -0.928   0.113  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.052   1.593   1.225  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.601   3.125   0.240  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.824   1.590  -0.120  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.394  -0.814  -0.194  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.001  -3.441  -1.092  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.442  -2.163  -0.082  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5    6    6
CONECT    5   24
CONECT    6    7   25
CONECT    7    8   19   19
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   26
CONECT   14   15   15   27
CONECT   15   16   17
CONECT   16   28
CONECT   17   18   18   29
CONECT   18   19
END

HMDB0030831
     RDKit          3D
Alternariol
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.4383   -2.0732   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -0.6450    0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -0.1690    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467    1.1432    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7036    1.5255    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    2.0731    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.6757    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    2.5638    0.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    2.2970    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    3.1951    0.0490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    0.9865   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    0.6755   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338    1.7374   -0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6323   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4106   -1.6444   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -2.9557   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.3500   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.0455   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    0.3105    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.6268    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5170   -2.5251   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -2.4790   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749   -0.9281    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.5930    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    3.1251    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238    1.5904   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3941   -0.8141   -0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013   -3.4406   -1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4425   -2.1626   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',5-Trihydroxy-6'-methyldibenzo-alpha-pyrone	ChEBI
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone	ChEBI
AOH	ChEBI
3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone	Generator
3,4',5-Trihydroxy-6'-methyldibenzo-α-pyrone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate g-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate gamma-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate γ-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid g-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid γ-lactone	Generator
1-Methyl-3,7,9-trihydroxy-6H-dibenzo(b,D)pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,D)pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9ci	HMDB
Alternariol 3,4',5-trihydroxy-6'-methyl-dibenzo[a]pyrone	HMDB
Alternariol from alternaria sp.	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Molecular Weight

258.2262

Monoisotopic Molecular Weight

258.05282343

IUPAC Name

3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one

Traditional Name

alternariol

CAS Registry Number

641-38-3

SMILES

CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

InChI Key

CEBXXEKPIIDJHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Isocoumarin
Benzopyran
1-benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:64983 )
benzochromenone (CHEBI:64983 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	350 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	61.89 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.49	ALOGPS
logP	3.18	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.92 m³·mol⁻¹	ChemAxon
Polarizability	25.14 Å³	ChemAxon
Number of Rings	3	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]+	158.856	31661259
DarkChem	[M-H]-	156.858	31661259
DeepCCS	[M+H]+	161.837	30932474
DeepCCS	[M-H]-	159.479	30932474
DeepCCS	[M-2H]-	192.365	30932474
DeepCCS	[M+Na]+	167.93	30932474
AllCCS	[M+H]+	155.9	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	156.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.64 minutes	32390414
Predicted by Siyang on May 30, 2022	12.401 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1855.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	125.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	570.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	446.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	848.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1508.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	470.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	240.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	194.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alternariol	CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1	4197.8	Standard polar	33892256
Alternariol	CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1	2631.4	Standard non polar	33892256
Alternariol	CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1	3016.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alternariol,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2=C1C1=CC(O)=CC(O)=C1C(=O)O2	2843.6	Semi standard non polar	33892256
Alternariol,1TMS,isomer #2	CC1=CC(O)=CC2=C1C1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)O2	2782.3	Semi standard non polar	33892256
Alternariol,1TMS,isomer #3	CC1=CC(O)=CC2=C1C1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)O2	2832.9	Semi standard non polar	33892256
Alternariol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2=C1C1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)O2	2801.8	Semi standard non polar	33892256
Alternariol,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC2=C1C1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)O2	2888.9	Semi standard non polar	33892256
Alternariol,2TMS,isomer #3	CC1=CC(O)=CC2=C1C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)O2	2796.5	Semi standard non polar	33892256
Alternariol,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2=C1C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)O2	2891.8	Semi standard non polar	33892256
Alternariol,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC(O)=CC(O)=C1C(=O)O2	3077.4	Semi standard non polar	33892256
Alternariol,1TBDMS,isomer #2	CC1=CC(O)=CC2=C1C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O2	3012.6	Semi standard non polar	33892256
Alternariol,1TBDMS,isomer #3	CC1=CC(O)=CC2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)O2	3063.5	Semi standard non polar	33892256
Alternariol,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O2	3245.6	Semi standard non polar	33892256
Alternariol,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)O2	3323.5	Semi standard non polar	33892256
Alternariol,2TBDMS,isomer #3	CC1=CC(O)=CC2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O2	3243.5	Semi standard non polar	33892256
Alternariol,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O2	3593.7	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 - Alternariol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu3-0190000000-ab90d95f25f23b1c1d4d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alternariol GC-MS (3 TMS) - 70eV, Positive	splash10-11b9-2202900000-492de99142b0a0d1994c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alternariol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alternariol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alternariol DI-ESI-qTof , Positive-QTOF	splash10-0a4i-0090000000-49a9dc87e5577f9cc6aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alternariol , positive-QTOF	splash10-0a4i-0290000000-913a843eb1fbe0ab9082	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alternariol , positive-QTOF	splash10-0a4i-0490000000-4c5e72338325be202711	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 10V, Positive-QTOF	splash10-0a4i-0090000000-95b8c497427d61e438f4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 20V, Positive-QTOF	splash10-0a4i-0090000000-51f692a816351a0b1b59	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 40V, Positive-QTOF	splash10-05mo-1290000000-46150e766500f30952d8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 10V, Negative-QTOF	splash10-0a4i-0090000000-353041795899e746b989	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 20V, Negative-QTOF	splash10-0a4i-0090000000-7411b04aa0ed4ee2981d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 40V, Negative-QTOF	splash10-066u-1390000000-b231ee41769f3f5f967a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 10V, Positive-QTOF	splash10-0a4i-0090000000-adb7dbccff647a617461	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 20V, Positive-QTOF	splash10-0a4i-0090000000-adb7dbccff647a617461	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 40V, Positive-QTOF	splash10-001u-0980000000-b815e685470eef6d7042	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 10V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 20V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alternariol 40V, Negative-QTOF	splash10-05mo-1190000000-3f7f323bf357ac1a8f9d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alternariol

METLIN ID

Not Available

PubChem Compound

5359485

PDB ID

Not Available

ChEBI ID

64983

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1701901

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Alternariol → 6-({3,7-dihydroxy-1-methyl-6-oxo-6H-benzo[c]chromen-9-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Alternariol → 6-({3,9-dihydroxy-1-methyl-6-oxo-6H-benzo[c]chromen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Alternariol → 6-({7,9-dihydroxy-1-methyl-6-oxo-6H-benzo[c]chromen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Alternariol (HMDB0030831)

MOL for HMDB0030831 (Alternariol)

3D MOL for HMDB0030831 (Alternariol)

3D SDF for HMDB0030831 (Alternariol)

3D-SDF for HMDB0030831 (Alternariol)

PDB for HMDB0030831 (Alternariol)

3D PDB for HMDB0030831 (Alternariol)

SMILES for HMDB0030831 (Alternariol)

INCHI for HMDB0030831 (Alternariol)

Structure for HMDB0030831 (Alternariol)

3D Structure for HMDB0030831 (Alternariol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions