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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:24:35 UTC

Update Date

2022-03-07 02:53:48 UTC

HMDB ID

HMDB0033658

Secondary Accession Numbers

HMDB33658

Metabolite Identification

Common Name

De-O-methyldihydrosterigmatocystin

Description

De-O-methyldihydrosterigmatocystin 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 very few articles have been published on De-O-methyldihydrosterigmatocystin.

Structure

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

HMDB0033658
     RDKit          3D
De-O-methyldihydrosterigmatocystin
 35 39  0  0  0  0  0  0  0  0999 V2000
    2.7389   -2.3413    0.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -1.3615    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -0.1451    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    0.0322    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578   -0.9887    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633    1.3247    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763    2.3903   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    2.2194   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    0.9401   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093    0.8299   -0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -0.2716   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -0.3197   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.5353   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -2.6649    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -2.6391    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -3.8153    0.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749   -1.4212    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -1.3737   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -0.1381   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7533    0.4867   -0.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.7254    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9650    1.4314    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4302    0.6586   -0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -1.9270    0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    1.4585    0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784    3.4052   -0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    3.0616   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -3.5919    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -4.1074    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7398   -0.2387   -2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    2.0797    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    2.4544   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096    0.7102    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4131    2.3396    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    1.3328   -1.4992 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  1  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
 21 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  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  1  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>
HMDB0033658

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/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/h1-3,6-7,17-19H,4-5H2

> <INCHI_KEY>
WUSMTEDKVPWFDN-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.120479379633892

> <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),10,14,16,18-hexaen-13-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
3.59071859

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.962030498671357

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.311718569680691

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2099162827964784

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
79.1272

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-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),10,14,16,18-hexaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033658
     RDKit          3D
De-O-methyldihydrosterigmatocystin
 35 39  0  0  0  0  0  0  0  0999 V2000
    2.7389   -2.3413    0.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -1.3615    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -0.1451    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    0.0322    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578   -0.9887    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633    1.3247    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763    2.3903   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    2.2194   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    0.9401   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093    0.8299   -0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -0.2716   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -0.3197   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.5353   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -2.6649    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -2.6391    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -3.8153    0.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749   -1.4212    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -1.3737   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -0.1381   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7533    0.4867   -0.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.7254    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9650    1.4314    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4302    0.6586   -0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -1.9270    0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    1.4585    0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784    3.4052   -0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    3.0616   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -3.5919    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -4.1074    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7398   -0.2387   -2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    2.0797    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    2.4544   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096    0.7102    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4131    2.3396    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    1.3328   -1.4992 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  1  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
 21 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  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    HMDB0033658
HETATM    1  O1  UNL     1       2.739  -2.341   0.654  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.045  -1.362   0.365  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.683  -0.145   0.216  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.035   0.032   0.370  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.858  -0.989   0.685  1.00  0.00           O  
HETATM    6  C4  UNL     1       4.563   1.325   0.190  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.776   2.390  -0.129  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.421   2.219  -0.285  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.902   0.940  -0.106  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.609   0.830  -0.265  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.057  -0.272  -0.143  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.412  -0.320  -0.322  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.057  -1.535  -0.174  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.341  -2.665   0.148  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.046  -2.639   0.336  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.651  -3.815   0.652  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.675  -1.421   0.185  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.419  -1.374  -0.396  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.686  -0.138  -1.032  1.00  0.00           C  
HETATM   20  O6  UNL     1      -4.753   0.487  -0.459  1.00  0.00           O  
HETATM   21  C15 UNL     1      -4.375   1.725   0.003  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.965   1.431   0.529  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.430   0.659  -0.659  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.828  -1.927   0.865  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.629   1.458   0.313  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.178   3.405  -0.272  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.761   3.062  -0.542  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.858  -3.592   0.257  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.554  -4.107   0.835  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.740  -0.239  -2.133  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.034   2.080   0.812  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.244   2.454  -0.819  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.010   0.710   1.376  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.413   2.340   0.752  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.159   1.333  -1.499  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   31   32
CONECT   22   23   33   34
CONECT   23   35
END

HMDB0033658
     RDKit          3D
De-O-methyldihydrosterigmatocystin
 35 39  0  0  0  0  0  0  0  0999 V2000
    2.7389   -2.3413    0.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -1.3615    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -0.1451    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    0.0322    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578   -0.9887    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633    1.3247    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763    2.3903   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    2.2194   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    0.9401   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093    0.8299   -0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -0.2716   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -0.3197   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.5353   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -2.6649    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -2.6391    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -3.8153    0.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749   -1.4212    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -1.3737   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -0.1381   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7533    0.4867   -0.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    1.7254    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9650    1.4314    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4302    0.6586   -0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -1.9270    0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    1.4585    0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784    3.4052   -0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    3.0616   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -3.5919    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -4.1074    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7398   -0.2387   -2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    2.0797    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    2.4544   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096    0.7102    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4131    2.3396    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    1.3328   -1.4992 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  1  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
 21 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Demethyldihydrosterigmatocystin	HMDB
Dihydrodemethylsterigmatocystin	HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

IUPAC Name

11,15-dihydroxy-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

11,15-dihydroxy-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

30517-66-9

SMILES

OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2

InChI Identifier

InChI=1S/C17H12O6/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/h1-3,6-7,17-19H,4-5H2

InChI Key

WUSMTEDKVPWFDN-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Vinylogous acid
Oxacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-4586 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	202 °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	0.4 g/L	ALOGPS
logP	2.42	ALOGPS
logP	3.59	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.31	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	79.13 m³·mol⁻¹	ChemAxon
Polarizability	30.12 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]+	167.957	31661259
DarkChem	[M-H]-	165.662	31661259
DeepCCS	[M+H]+	169.381	30932474
DeepCCS	[M-H]-	167.023	30932474
DeepCCS	[M-2H]-	200.823	30932474
DeepCCS	[M+Na]+	176.05	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	173.7	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.	6.45 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9782 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2611.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	369.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	208.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	564.9 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	756.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1227.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.4 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	1609.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	232.1 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	135.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
De-O-methyldihydrosterigmatocystin	OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	4467.7	Standard polar	33892256
De-O-methyldihydrosterigmatocystin	OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	2922.4	Standard non polar	33892256
De-O-methyldihydrosterigmatocystin	OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2	2944.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
De-O-methyldihydrosterigmatocystin,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O2	3121.2	Semi standard non polar	33892256
De-O-methyldihydrosterigmatocystin,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O2	3118.2	Semi standard non polar	33892256
De-O-methyldihydrosterigmatocystin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C3OC4OCCC4C3=C1O2	3199.0	Semi standard non polar	33892256
De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O2	3349.7	Semi standard non polar	33892256
De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O2	3344.4	Semi standard non polar	33892256
De-O-methyldihydrosterigmatocystin,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=C3OC4OCCC4C3=C1O2	3642.0	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 - De-O-methyldihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1190000000-333fc0c025f1a0991340	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-4504900000-8ec5367a9cfefcd1ddae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin 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-methyldihydrosterigmatocystin 10V, Positive-QTOF	splash10-03di-0029000000-68b36ea43dfc30c09a62	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOF	splash10-03di-0089000000-cf4f2b4c6375ec0ef1c1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOF	splash10-01ta-1490000000-30ce98d0cdc6ae50dda8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOF	splash10-03di-0009000000-fdfe47d21a035416c9dc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOF	splash10-03di-0139000000-f9058f433c1086d6f0ca	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOF	splash10-00ou-1390000000-6148302a8c000974ec2e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOF	splash10-01ow-0591000000-4fa22d9ff53e113d690c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOF	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOF	splash10-03di-0049000000-3b842f4e2555c65afd0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOF	splash10-029x-1390000000-59c8649686b037aa2c65	2021-09-25	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

FDB011760

KNApSAcK ID

Not Available

Chemspider ID

4588953

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5486528

PDB ID

Not Available

ChEBI ID

174245

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

Showing metabocard for De-O-methyldihydrosterigmatocystin (HMDB0033658)

MOL for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

3D MOL for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

3D SDF for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

3D-SDF for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

PDB for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

3D PDB for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

SMILES for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

INCHI for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

Structure for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

3D Structure for HMDB0033658 (De-O-methyldihydrosterigmatocystin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions