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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:49 UTC

Update Date

2022-03-07 02:52:36 UTC

HMDB ID

HMDB0030590

Secondary Accession Numbers

HMDB30590

Metabolite Identification

Common Name

Dihydrosterigmatocystin

Description

Dihydrosterigmatocystin 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 Dihydrosterigmatocystin.

Structure

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

HMDB0030590
     RDKit          3D
Dihydrosterigmatocystin
 38 42  0  0  0  0  0  0  0  0999 V2000
   -0.7427    4.4472   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    3.1476   -0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911    2.1120   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743    2.2817   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    1.2352   -0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.0149    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484   -0.1769    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4589   -1.3561    0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -1.5584    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.8573    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -3.1150    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4526   -2.1306    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390   -0.8117   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629    0.1247   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.5763    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.7020   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.6529   -0.5714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973    0.8581   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.9088    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1024   -1.6249   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5899   -1.5858   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632   -0.5358    0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.0437    0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210    1.1745    0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    4.4041   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    4.9459   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    4.9720   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682    3.2607   -0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811   -3.6164    0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -4.1185    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043   -2.3157    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    1.0353   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -1.6018    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.6995   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.0990   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -2.5212    0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.4671   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    0.2939    1.9456 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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 18  3  1  0
 23 19  1  0
 24  5  1  0
 18  7  2  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 23 38  1  0
M  END


  Mrv0541 05061305222D          

 24 28  0  0  0  0            999 V2000
    3.1579    6.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.9820    3.2731    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
    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
    3.5256    5.3870    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
   -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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  6  1  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030590

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-4,7-8,18-19H,5-6H2,1H3

> <INCHI_KEY>
RHGQIWVTIHZRLI-UHFFFAOYSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.3002

> <EXACT_MASS>
326.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.182394521315146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.086612646

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.582974385264885

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158168155625468

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
83.6095

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030590
     RDKit          3D
Dihydrosterigmatocystin
 38 42  0  0  0  0  0  0  0  0999 V2000
   -0.7427    4.4472   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    3.1476   -0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911    2.1120   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743    2.2817   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    1.2352   -0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.0149    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484   -0.1769    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4589   -1.3561    0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -1.5584    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.8573    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -3.1150    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4526   -2.1306    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390   -0.8117   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629    0.1247   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.5763    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.7020   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.6529   -0.5714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973    0.8581   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.9088    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1024   -1.6249   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5899   -1.5858   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632   -0.5358    0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.0437    0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210    1.1745    0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    4.4041   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    4.9459   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    4.9720   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682    3.2607   -0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811   -3.6164    0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -4.1185    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043   -2.3157    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    1.0353   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -1.6018    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.6995   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.0990   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -2.5212    0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.4671   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    0.2939    1.9456 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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 18  3  1  0
 23 19  1  0
 24  5  1  0
 18  7  2  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 23 38  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       5.895  11.434   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.790   4.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.641   5.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.253   4.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.452   5.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.071   4.853   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.970  10.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.707   6.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.954   7.299   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       3.507  10.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.119   9.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.806   7.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.417   7.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.193   8.867   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.731   8.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.343   7.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.659   7.311   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.805   8.583   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       4.358  11.529   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.758   6.232   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.029   6.204   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.404   8.829   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   10                                                       
CONECT    5    6    8                                                       
CONECT    6    5   22                                                       
CONECT    7   11   12                                                       
CONECT    8    5   13   18                                                  
CONECT    9    3   14   19                                                  
CONECT   10    4   14   23                                                  
CONECT   11    7   15   21                                                  
CONECT   12    7   13   24                                                  
CONECT   13    8   12   17                                                  
CONECT   14    9   10   16                                                  
CONECT   15   11   16   17                                                  
CONECT   16   14   15   20                                                  
CONECT   17   13   15   23                                                  
CONECT   18    8   22   24                                                  
CONECT   19    9                                                            
CONECT   20   16                                                            
CONECT   21    1   11                                                       
CONECT   22    6   18                                                       
CONECT   23   10   17                                                       
CONECT   24   12   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0030590
HETATM    1  C1  UNL     1      -0.743   4.447  -1.077  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.157   3.148  -0.788  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.291   2.112  -0.451  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.074   2.282  -0.371  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.941   1.235  -0.030  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.423  -0.015   0.237  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.048  -0.177   0.154  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.459  -1.356   0.404  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.777  -1.558   0.337  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.208  -2.857   0.624  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.557  -3.115   0.567  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.453  -2.131   0.240  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.039  -0.812  -0.054  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.963   0.125  -0.372  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.682  -0.576   0.009  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.179   0.702  -0.267  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.914   1.653  -0.571  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.797   0.858  -0.182  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.569  -0.909   0.566  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.102  -1.625  -0.655  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.590  -1.586  -0.393  1.00  0.00           C  
HETATM   22  O5  UNL     1       4.863  -0.536   0.437  1.00  0.00           O  
HETATM   23  C18 UNL     1       3.703   0.044   0.869  1.00  0.00           C  
HETATM   24  O6  UNL     1       3.321   1.174   0.109  1.00  0.00           O  
HETATM   25  H1  UNL     1       0.160   4.404  -1.723  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.515   4.946  -0.090  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.582   4.972  -1.603  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.468   3.261  -0.581  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.481  -3.616   0.879  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.940  -4.119   0.784  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.504  -2.316   0.191  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.907   1.035  -0.596  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.366  -1.602   1.379  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.810  -2.699  -0.667  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.903  -1.099  -1.593  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.936  -2.521   0.127  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.176  -1.467  -1.331  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.694   0.294   1.946  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   19
CONECT    7    8   18   18
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   15   15
CONECT   14   32
CONECT   15   16
CONECT   16   17   17   18
CONECT   19   20   23   33
CONECT   20   21   34   35
CONECT   21   22   36   37
CONECT   22   23
CONECT   23   24   38
END

HMDB0030590
     RDKit          3D
Dihydrosterigmatocystin
 38 42  0  0  0  0  0  0  0  0999 V2000
   -0.7427    4.4472   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    3.1476   -0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911    2.1120   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743    2.2817   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    1.2352   -0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.0149    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484   -0.1769    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4589   -1.3561    0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -1.5584    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.8573    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -3.1150    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4526   -2.1306    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390   -0.8117   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629    0.1247   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.5763    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.7020   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.6529   -0.5714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973    0.8581   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.9088    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1024   -1.6249   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5899   -1.5858   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632   -0.5358    0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.0437    0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210    1.1745    0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    4.4041   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    4.9459   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    4.9720   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682    3.2607   -0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811   -3.6164    0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -4.1185    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043   -2.3157    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    1.0353   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -1.6018    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.6995   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.0990   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -2.5212    0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.4671   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    0.2939    1.9456 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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 18  3  1  0
 23 19  1  0
 24  5  1  0
 18  7  2  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydro-6-methoxy-7-hydroxyfuroxanthone	HMDB
5-Hydroxydihydrosterigmatocystin	HMDB

Chemical Formula

C₁₈H₁₄O₆

Average Molecular Weight

326.3002

Monoisotopic Molecular Weight

326.07903818

IUPAC Name

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

Traditional Name

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

CAS Registry Number

6795-16-0

SMILES

COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

InChI Identifier

InChI=1S/C18H14O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-4,7-8,18-19H,5-6H2,1H3

InChI Key

RHGQIWVTIHZRLI-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
Benzopyran
1-benzopyran
Coumaran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Tetrahydrofuran
Ether
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-4587 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030590)
Cell membrane (HMDB: HMDB0030590)

Source

Endogenous

Endogenous (HMDB: HMDB0030590)

Exogenous

Food

Food (HMDB: HMDB0030590)

Exogenous (HMDB: HMDB0030590)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230 °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	0.26 g/L	ALOGPS
logP	2.56	ALOGPS
logP	3.09	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	32.18 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]+	174.313	31661259
DarkChem	[M-H]-	172.889	31661259
DeepCCS	[M+H]+	175.657	30932474
DeepCCS	[M-H]-	173.299	30932474
DeepCCS	[M-2H]-	207.408	30932474
DeepCCS	[M+Na]+	182.908	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	177.5	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	179.6	32859911
AllCCS	[M+HCOO]-	178.9	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.	7.21 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9563 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2482.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	358.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.6 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	665.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1260.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	458.0 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	1502.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.5 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	65.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrosterigmatocystin	COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	4414.3	Standard polar	33892256
Dihydrosterigmatocystin	COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	2964.3	Standard non polar	33892256
Dihydrosterigmatocystin	COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	3076.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrosterigmatocystin,1TMS,isomer #1	COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O3)C1CCOC1O2	3154.5	Semi standard non polar	33892256
Dihydrosterigmatocystin,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O3)C1CCOC1O2	3358.0	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 - Dihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-1191000000-3169260a64a28510a099	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrosterigmatocystin GC-MS (1 TMS) - 70eV, Positive	splash10-0v5i-2019000000-18bb22e5571b45faf21c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrosterigmatocystin 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 - Dihydrosterigmatocystin 10V, Positive-QTOF	splash10-004i-0019000000-26331fd365b17b31be60	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Positive-QTOF	splash10-004i-0049000000-ce5d50d5caadee2491e4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Positive-QTOF	splash10-004r-2690000000-8fd21453b9e79b63ffc8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Negative-QTOF	splash10-004i-0009000000-ac63595de65f6b74b494	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Negative-QTOF	splash10-004i-0029000000-fe1061c93c12df43c49f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Negative-QTOF	splash10-014i-2491000000-cdb32ce1175da48f2e88	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Positive-QTOF	splash10-004i-0009000000-fdece4c688aa8992d2ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Positive-QTOF	splash10-004i-0009000000-73afc3fef5344749693e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Positive-QTOF	splash10-055b-0293000000-391354040c44dbd70bc8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Negative-QTOF	splash10-004i-0009000000-eb8469b649b7c5d99242	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Negative-QTOF	splash10-004i-0049000000-55ef06ecfac0c9d504a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Negative-QTOF	splash10-06xt-1494000000-795297f194352894e731	2021-09-25	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

FDB002483

KNApSAcK ID

C00023633

Chemspider ID

4588884

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5486173

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.. .

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

Dihydrosterigmatocystin → 3,4,5-trihydroxy-6-({11-methoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14(19),15,17-hexaen-15-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Dihydrosterigmatocystin (HMDB0030590)

MOL for HMDB0030590 (Dihydrosterigmatocystin)

3D MOL for HMDB0030590 (Dihydrosterigmatocystin)

3D SDF for HMDB0030590 (Dihydrosterigmatocystin)

3D-SDF for HMDB0030590 (Dihydrosterigmatocystin)

PDB for HMDB0030590 (Dihydrosterigmatocystin)

3D PDB for HMDB0030590 (Dihydrosterigmatocystin)

SMILES for HMDB0030590 (Dihydrosterigmatocystin)

INCHI for HMDB0030590 (Dihydrosterigmatocystin)

Structure for HMDB0030590 (Dihydrosterigmatocystin)

3D Structure for HMDB0030590 (Dihydrosterigmatocystin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions