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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:24:32 UTC

Update Date

2022-03-07 02:53:48 UTC

HMDB ID

HMDB0033657

Secondary Accession Numbers

HMDB33657

Metabolite Identification

Common Name

De-O-methylsterigmatocystin

Description

De-O-methylsterigmatocystin belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp. Based on a literature review a significant number of articles have been published on De-O-methylsterigmatocystin.

Structure

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

HMDB0033657
     RDKit          3D
De-O-methylsterigmatocystin
 33 37  0  0  0  0  0  0  0  0999 V2000
   -2.3304    2.4379   -0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    1.3385    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    0.1692    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.1848    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221    1.3148    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5736   -1.0304    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309   -2.1690    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -2.1898    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9969    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4370   -1.0448    0.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    0.0399    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756   -0.0043    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048    1.1516   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    2.3457   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    2.4064   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405    3.6191   -0.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750    1.2471    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720    0.8169   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -0.4091    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8852   -1.2203   -0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7153   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -1.6701   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -1.1144    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539    2.2203    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6554   -1.0055    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3879   -3.0968    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -3.0916    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181    3.2548   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    4.4927   -0.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -0.3180    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -2.0830   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -1.9872   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435   -1.8935    0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 17  2  1  0
 23 19  1  0
  9  3  1  0
 17 11  1  0
 23 12  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END


  Mrv0541 05061307162D          

 23 27  0  0  0  0            999 V2000
    4.1732    2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289    3.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    2.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421    2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553    5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3787    3.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    3.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8788    5.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9820    3.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    4.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674    4.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465    4.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    3.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168    4.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    6.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256    5.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    3.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    4.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 15  2  0  0  0  0
 21  5  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033657

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H10O6/c18-8-2-1-3-10-13(8)15(20)14-9(19)6-11-12(16(14)22-10)7-4-5-21-17(7)23-11/h1-7,17-19H

> <INCHI_KEY>
RQQOEIJLJPCYJR-UHFFFAOYSA-N

> <FORMULA>
C17H10O6

> <MOLECULAR_WEIGHT>
310.2577

> <EXACT_MASS>
310.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.49243344175418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.602697635

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.853174751607181

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.18807939680714

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2369126095468745

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
79.22030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033657
     RDKit          3D
De-O-methylsterigmatocystin
 33 37  0  0  0  0  0  0  0  0999 V2000
   -2.3304    2.4379   -0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    1.3385    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    0.1692    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.1848    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221    1.3148    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5736   -1.0304    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309   -2.1690    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -2.1898    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9969    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4370   -1.0448    0.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    0.0399    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756   -0.0043    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048    1.1516   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    2.3457   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    2.4064   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405    3.6191   -0.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750    1.2471    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720    0.8169   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -0.4091    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8852   -1.2203   -0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7153   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -1.6701   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -1.1144    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539    2.2203    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6554   -1.0055    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3879   -3.0968    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -3.0916    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181    3.2548   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    4.4927   -0.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -0.3180    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -2.0830   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -1.9872   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435   -1.8935    0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 17  2  1  0
 23 19  1  0
  9  3  1  0
 17 11  1  0
 23 12  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.790   4.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.641   5.920   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.253   4.731   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.452   5.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.071   4.853   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.970  10.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.707   6.599   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.954   7.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.507  10.245   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.566   6.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.119   9.056   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.806   7.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.417   7.393   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.193   8.867   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.731   8.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.343   7.583   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.659   7.311   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.805   8.583   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.358  11.529   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.581  10.056   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.758   6.232   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.029   6.204   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.404   8.829   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1   10                                                       
CONECT    4    5    7                                                       
CONECT    5    4   21                                                       
CONECT    6    9   11                                                       
CONECT    7    4   12   17                                                  
CONECT    8    2   13   18                                                  
CONECT    9    6   14   19                                                  
CONECT   10    3   13   22                                                  
CONECT   11    6   12   23                                                  
CONECT   12    7   11   16                                                  
CONECT   13    8   10   15                                                  
CONECT   14    9   15   16                                                  
CONECT   15   13   14   20                                                  
CONECT   16   12   14   22                                                  
CONECT   17    7   21   23                                                  
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   15                                                            
CONECT   21    5   17                                                       
CONECT   22   10   16                                                       
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0033657
HETATM    1  O1  UNL     1      -2.330   2.438  -0.073  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.765   1.339   0.041  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.481   0.169   0.210  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.872   0.185   0.259  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.622   1.315   0.148  1.00  0.00           O  
HETATM    6  C4  UNL     1      -4.574  -1.030   0.433  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.831  -2.169   0.545  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.464  -2.190   0.498  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.757  -0.997   0.326  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.437  -1.045   0.284  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.277   0.040   0.125  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.676  -0.004   0.079  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.405   1.152  -0.089  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.729   2.346  -0.210  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.353   2.406  -0.168  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.341   3.619  -0.291  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.375   1.247   0.001  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.772   0.817  -0.098  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.923  -0.409   0.586  1.00  0.00           C  
HETATM   20  O6  UNL     1       4.885  -1.220  -0.039  1.00  0.00           O  
HETATM   21  C15 UNL     1       4.349  -1.715  -1.219  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.035  -1.670  -1.131  1.00  0.00           C  
HETATM   23  C17 UNL     1       2.625  -1.114   0.179  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.354   2.220   0.028  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.655  -1.006   0.470  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.388  -3.097   0.679  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.884  -3.092   0.587  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.318   3.255  -0.343  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.133   4.493  -0.415  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.025  -0.318   1.662  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.929  -2.083  -2.082  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.353  -1.987  -1.892  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.343  -1.894   0.910  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   23
CONECT   13   14   14   18
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   16   29
CONECT   18   19
CONECT   19   20   23   30
CONECT   20   21
CONECT   21   22   22   31
CONECT   22   23   32
CONECT   23   33
END

HMDB0033657
     RDKit          3D
De-O-methylsterigmatocystin
 33 37  0  0  0  0  0  0  0  0999 V2000
   -2.3304    2.4379   -0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    1.3385    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    0.1692    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.1848    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221    1.3148    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5736   -1.0304    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309   -2.1690    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -2.1898    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9969    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4370   -1.0448    0.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    0.0399    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756   -0.0043    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048    1.1516   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    2.3457   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    2.4064   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405    3.6191   -0.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750    1.2471    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720    0.8169   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -0.4091    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8852   -1.2203   -0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7153   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -1.6701   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -1.1144    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539    2.2203    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6554   -1.0055    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3879   -3.0968    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -3.0916    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181    3.2548   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    4.4927   -0.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -0.3180    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -2.0830   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -1.9872   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435   -1.8935    0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 17  2  1  0
 23 19  1  0
  9  3  1  0
 17 11  1  0
 23 12  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Demethylsterigmatocystin	HMDB
Demethylsterigmatocystin	HMDB

Chemical Formula

C₁₇H₁₀O₆

Average Molecular Weight

310.2577

Monoisotopic Molecular Weight

310.047738052

IUPAC Name

11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one

Traditional Name

11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one

CAS Registry Number

30461-65-5

SMILES

OC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

InChI Identifier

InChI=1S/C17H10O6/c18-8-2-1-3-10-13(8)15(20)14-9(19)6-11-12(16(14)22-10)7-4-5-21-17(7)23-11/h1-7,17-19H

InChI Key

RQQOEIJLJPCYJR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Sterigmatocystins

Sub Class

Not Available

Direct Parent

Sterigmatocystins

Alternative Parents

Substituents

Sterigmatocystin backbone
Xanthone
Dibenzopyran
Xanthene
Chromone
1-benzopyran
Benzopyran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Dihydrofuran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (6-DEMETHYLSTERIGMATOCYSTIN )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033657)
Cell membrane (HMDB: HMDB0033657)

Source

Exogenous

Exogenous (HMDB: HMDB0033657)

Food

Food (HMDB: HMDB0033657)

Endogenous

Plant

Plant (HMDB: HMDB0033657)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033657)

Environmental role

Environmental contaminant (HMDB: HMDB0033657)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	253 - 255 °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	0.38 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.6	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.22 m³·mol⁻¹	ChemAxon
Polarizability	29.49 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]+	167.677	31661259
DarkChem	[M-H]-	164.516	31661259
DeepCCS	[M+H]+	169.947	30932474
DeepCCS	[M-H]-	167.589	30932474
DeepCCS	[M-2H]-	201.368	30932474
DeepCCS	[M+Na]+	176.595	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	173.5	32859911
AllCCS	[M+Na-2H]-	172.4	32859911
AllCCS	[M+HCOO]-	171.3	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.	6.37 minutes	32390414
Predicted by Siyang on May 30, 2022	16.556 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2989.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	477.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	297.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	504.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	649.5 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	948.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	176.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1497.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	552.4 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	1770.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	532.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	601.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	355.2 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	135.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
De-O-methylsterigmatocystin	OC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	4459.8	Standard polar	33892256
De-O-methylsterigmatocystin	OC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	2855.8	Standard non polar	33892256
De-O-methylsterigmatocystin	OC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	2837.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
De-O-methylsterigmatocystin,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1C=COC1O2	3121.7	Semi standard non polar	33892256
De-O-methylsterigmatocystin,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OC=CC4C3=C1O2	3130.2	Semi standard non polar	33892256
De-O-methylsterigmatocystin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C3OC4OC=CC4C3=C1O2	3192.6	Semi standard non polar	33892256
De-O-methylsterigmatocystin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1C=COC1O2	3344.0	Semi standard non polar	33892256
De-O-methylsterigmatocystin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OC=CC4C3=C1O2	3340.6	Semi standard non polar	33892256
De-O-methylsterigmatocystin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C3OC4OC=CC4C3=C1O2	3624.6	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 - De-O-methylsterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1090000000-f736ceb0ac81e8c9d33d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - De-O-methylsterigmatocystin GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-5407900000-29bb2816c70bb4272d58	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - De-O-methylsterigmatocystin 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 - De-O-methylsterigmatocystin 10V, Positive-QTOF	splash10-03di-0029000000-13bba40d0579b0a7f79f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 20V, Positive-QTOF	splash10-03di-0069000000-8b0d618ed676e55015b9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 40V, Positive-QTOF	splash10-002f-1390000000-0605c79d89b49a3d3d9e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 10V, Negative-QTOF	splash10-0a4i-0009000000-be60baaef5bb34727170	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 20V, Negative-QTOF	splash10-0a4i-0129000000-7699c369daa881a6a9bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 40V, Negative-QTOF	splash10-00mo-2390000000-df477a34f1dec5ddae27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 10V, Positive-QTOF	splash10-03di-0009000000-28600f1becbfb2f043c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 20V, Positive-QTOF	splash10-03di-0009000000-28600f1becbfb2f043c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 40V, Positive-QTOF	splash10-03e9-0494000000-829de2f4df57895c0a44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 10V, Negative-QTOF	splash10-0a4i-0009000000-f9b5f854b100ac09f3d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 20V, Negative-QTOF	splash10-0a4i-0029000000-56bf4afe0e86b9c57b03	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methylsterigmatocystin 40V, Negative-QTOF	splash10-0a4i-0496000000-f800173d29b93a6327b8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB011759

KNApSAcK ID

Not Available

Chemspider ID

4588891

KEGG Compound ID

C03683

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5486185

PDB ID

Not Available

ChEBI ID

174227

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.. .

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

De-O-methylsterigmatocystin → 3,4,5-trihydroxy-6-({11-hydroxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-15-yl}oxy)oxane-2-carboxylic acid	details
De-O-methylsterigmatocystin → 3,4,5-trihydroxy-6-({15-hydroxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-11-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for De-O-methylsterigmatocystin (HMDB0033657)

MOL for HMDB0033657 (De-O-methylsterigmatocystin)

3D MOL for HMDB0033657 (De-O-methylsterigmatocystin)

3D SDF for HMDB0033657 (De-O-methylsterigmatocystin)

3D-SDF for HMDB0033657 (De-O-methylsterigmatocystin)

PDB for HMDB0033657 (De-O-methylsterigmatocystin)

3D PDB for HMDB0033657 (De-O-methylsterigmatocystin)

SMILES for HMDB0033657 (De-O-methylsterigmatocystin)

INCHI for HMDB0033657 (De-O-methylsterigmatocystin)

Structure for HMDB0033657 (De-O-methylsterigmatocystin)

3D Structure for HMDB0033657 (De-O-methylsterigmatocystin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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