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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:33 UTC

Update Date

2021-09-14 15:47:25 UTC

HMDB ID

HMDB0041813

Secondary Accession Numbers

HMDB41813

Metabolite Identification

Common Name

6-Demethylgriseofulvin

Description

6-Demethylgriseofulvin belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review a significant number of articles have been published on 6-Demethylgriseofulvin.

Structure

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

HMDB0041813
     RDKit          3D
6-Demethylgriseofulvin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.1676    0.0485    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9590    0.6758    1.1848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    0.5103   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    0.6069   -1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030    0.4312   -2.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    1.0976   -3.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.5308   -2.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939   -0.8508   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710   -2.1548   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813    0.2357   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    1.3736   -0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    1.2211   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    1.7894   -0.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2224    2.9605   -2.1002 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4962    1.4871   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662    2.0870   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269    0.5703    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -0.0275    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.9502    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.2693    2.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    0.3028    0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.1238    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122   -0.6756    1.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0685    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0353    0.3625    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.2763    2.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.8097   -1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324   -0.0430   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.4874   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.9685   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9165   -2.7347   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -2.8300   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -1.9753    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    2.7529   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804    0.3246    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -2.0742    3.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099   -1.6117    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -0.3667    3.2987 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
M  END


  Mrv1652304062013052D          

 23 25  0  0  0  0            999 V2000
    2.9440    1.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    0.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    4.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    2.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    4.4952    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    2.8452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    3.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    1.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    1.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440    4.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    3.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  2  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18  8  2  0  0  0  0
 19  9  1  0  0  0  0
 20 15  2  0  0  0  0
 21  2  1  0  0  0  0
 21 10  1  0  0  0  0
 22  3  1  0  0  0  0
 22 11  1  0  0  0  0
 23 14  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041813

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C(=O)C3(OC2=C(Cl)C(O)=C1)C(C)CC(=O)C=C3OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(22-3)16(7)15(20)12-10(21-2)6-9(19)13(17)14(12)23-16/h5-7,19H,4H2,1-3H3

> <INCHI_KEY>
SYNGDIBHUPXIQA-UHFFFAOYSA-N

> <FORMULA>
C16H15ClO6

> <MOLECULAR_WEIGHT>
338.74

> <EXACT_MASS>
338.055715919

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.15096791023636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-6-hydroxy-2',4-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.0262434023333338

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.688685494632143

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.299241459222113

> <JCHEM_PKA_STRONGEST_BASIC>
-4.451043274150215

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
83.36359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-6-hydroxy-2',4-dimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041813
     RDKit          3D
6-Demethylgriseofulvin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.1676    0.0485    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9590    0.6758    1.1848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    0.5103   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    0.6069   -1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030    0.4312   -2.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    1.0976   -3.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.5308   -2.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939   -0.8508   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710   -2.1548   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813    0.2357   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    1.3736   -0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    1.2211   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    1.7894   -0.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2224    2.9605   -2.1002 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4962    1.4871   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662    2.0870   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269    0.5703    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -0.0275    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.9502    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.2693    2.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    0.3028    0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.1238    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122   -0.6756    1.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0685    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0353    0.3625    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.2763    2.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.8097   -1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324   -0.0430   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.4874   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.9685   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9165   -2.7347   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -2.8300   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -1.9753    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    2.7529   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804    0.3246    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -2.0742    3.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099   -1.6117    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -0.3667    3.2987 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       5.495   2.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.533   1.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.725   9.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.185   3.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.185   6.645   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.533   4.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.725   3.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.415   5.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.533   6.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.199   3.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.725   6.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865   4.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.199   6.851   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.865   6.081   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.401   4.065   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.495   5.311   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       9.199   8.391   0.000  0.00  0.00          Cl+0
HETATM   18  O   UNK     0       0.875   5.311   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      11.866   6.851   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.401   2.525   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.199   2.231   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.495   7.978   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.401   6.557   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    7    8                                                       
CONECT    5    8   11                                                       
CONECT    6    9   10                                                       
CONECT    7    1    4   16                                                  
CONECT    8    4    5   18                                                  
CONECT    9    6   13   19                                                  
CONECT   10    6   12   21                                                  
CONECT   11    5   16   22                                                  
CONECT   12   10   14   15                                                  
CONECT   13    9   14   17                                                  
CONECT   14   12   13   23                                                  
CONECT   15   12   16   20                                                  
CONECT   16    7   11   15   23                                             
CONECT   17   13                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   15                                                            
CONECT   21    2   10                                                       
CONECT   22    3   11                                                       
CONECT   23   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0041813
HETATM    1  C1  UNL     1      -4.168   0.049   1.579  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.959   0.676   1.185  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.398   0.510  -0.062  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.198   0.607  -1.110  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.603   0.431  -2.432  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.041   1.098  -3.433  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.484  -0.531  -2.596  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.794  -0.851  -1.313  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.271  -2.155  -0.702  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.981   0.236  -0.311  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.259   1.374  -0.756  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.077   1.221  -0.360  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.249   1.789  -0.793  1.00  0.00           C  
HETATM   14 CL1  UNL     1       2.222   2.961  -2.100  1.00  0.00          CL  
HETATM   15  C11 UNL     1       3.496   1.487  -0.246  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.666   2.087  -0.715  1.00  0.00           O  
HETATM   17  C12 UNL     1       3.527   0.570   0.779  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.380  -0.027   1.250  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.428  -0.950   2.284  1.00  0.00           O  
HETATM   20  C14 UNL     1       3.684  -1.269   2.852  1.00  0.00           C  
HETATM   21  C15 UNL     1       1.147   0.303   0.673  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.228  -0.124   0.915  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.612  -0.676   1.973  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.078  -1.068   1.527  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.035   0.362   0.977  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.369   0.276   2.643  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.261   0.810  -1.021  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.732  -0.043  -3.274  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.812  -1.487  -3.056  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.318  -0.969  -1.468  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.916  -2.735  -1.402  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.430  -2.830  -0.439  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.820  -1.975   0.252  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.570   2.753  -1.471  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.480   0.325   1.214  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.620  -2.074   3.596  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.410  -1.612   2.061  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.174  -0.367   3.299  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   27
CONECT    5    6    6    7
CONECT    7    8   28   29
CONECT    8    9   10   30
CONECT    9   31   32   33
CONECT   10   11   22
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   15
CONECT   15   16   17   17
CONECT   16   34
CONECT   17   18   35
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   36   37   38
CONECT   21   22
CONECT   22   23   23
END

HMDB0041813
     RDKit          3D
6-Demethylgriseofulvin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.1676    0.0485    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9590    0.6758    1.1848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    0.5103   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    0.6069   -1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030    0.4312   -2.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    1.0976   -3.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.5308   -2.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939   -0.8508   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710   -2.1548   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813    0.2357   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    1.3736   -0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    1.2211   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    1.7894   -0.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2224    2.9605   -2.1002 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4962    1.4871   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662    2.0870   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269    0.5703    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -0.0275    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.9502    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.2693    2.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    0.3028    0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.1238    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122   -0.6756    1.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0685    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0353    0.3625    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    0.2763    2.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.8097   -1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324   -0.0430   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.4874   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.9685   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9165   -2.7347   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -2.8300   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -1.9753    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    2.7529   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804    0.3246    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -2.0742    3.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099   -1.6117    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -0.3667    3.2987 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 10  3  1  0
 21 12  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Desmethylgriseofulvin	MeSH
6-Demethylgriseofulvin	MeSH

Chemical Formula

C₁₆H₁₅ClO₆

Average Molecular Weight

338.74

Monoisotopic Molecular Weight

338.055715919

IUPAC Name

7-chloro-6-hydroxy-2',4-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

Traditional Name

7-chloro-6-hydroxy-2',4-dimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

CAS Registry Number

20168-88-1

SMILES

COC1=C2C(=O)C3(OC2=C(Cl)C(O)=C1)C(C)CC(=O)C=C3OC

InChI Identifier

InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(22-3)16(7)15(20)12-10(21-2)6-9(19)13(17)14(12)23-16/h5-7,19H,4H2,1-3H3

InChI Key

SYNGDIBHUPXIQA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Cyclohexenone
Aryl chloride
Benzenoid
Aryl halide
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Ether
Organic oxygen compound
Organohalogen compound
Carbonyl group
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041813)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.095 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.03	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.3	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.36 m³·mol⁻¹	ChemAxon
Polarizability	32.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.976	30932474
DeepCCS	[M-H]-	174.618	30932474
DeepCCS	[M-2H]-	208.861	30932474
DeepCCS	[M+Na]+	184.088	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	178.1	32859911
AllCCS	[M+Na-2H]-	177.9	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Demethylgriseofulvin	COC1=C2C(=O)C3(OC2=C(Cl)C(O)=C1)C(C)CC(=O)C=C3OC	3954.2	Standard polar	33892256
6-Demethylgriseofulvin	COC1=C2C(=O)C3(OC2=C(Cl)C(O)=C1)C(C)CC(=O)C=C3OC	2655.5	Standard non polar	33892256
6-Demethylgriseofulvin	COC1=C2C(=O)C3(OC2=C(Cl)C(O)=C1)C(C)CC(=O)C=C3OC	2716.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Demethylgriseofulvin,1TMS,isomer #1	COC1=CC(=O)CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C)=CC(OC)=C1C2=O	2654.8	Semi standard non polar	33892256
6-Demethylgriseofulvin,1TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC(C)C12OC1=C(Cl)C(O)=CC(OC)=C1C2=O	2659.7	Semi standard non polar	33892256
6-Demethylgriseofulvin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C)=CC(OC)=C1C2=O	2672.7	Semi standard non polar	33892256
6-Demethylgriseofulvin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C)=CC(OC)=C1C2=O	2593.5	Standard non polar	33892256
6-Demethylgriseofulvin,1TBDMS,isomer #1	COC1=CC(=O)CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1C2=O	2874.7	Semi standard non polar	33892256
6-Demethylgriseofulvin,1TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C12OC1=C(Cl)C(O)=CC(OC)=C1C2=O	2879.0	Semi standard non polar	33892256
6-Demethylgriseofulvin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1C2=O	3116.2	Semi standard non polar	33892256
6-Demethylgriseofulvin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C12OC1=C(Cl)C(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1C2=O	3012.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fs-9115000000-2a9e51fa5516d222d279	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (1 TMS) - 70eV, Positive	splash10-0592-9407000000-6755598c62168fed3918	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Demethylgriseofulvin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 6-Demethylgriseofulvin 10V, Positive-QTOF	splash10-000i-0019000000-92950dfaf81abcab3681	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 20V, Positive-QTOF	splash10-1009-6659000000-6a6ac3f1b6fe6f1d9347	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 40V, Positive-QTOF	splash10-0pi3-9730000000-dfad982e0ee9fb0ebc6a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 10V, Negative-QTOF	splash10-000i-0009000000-8ff5e9fc392723b3ecc2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 20V, Negative-QTOF	splash10-000i-0029000000-dc30a869fa0bc3a1c2b7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 40V, Negative-QTOF	splash10-0596-6491000000-dcd83aa3125c317cd53b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 10V, Negative-QTOF	splash10-000i-0009000000-e580c42e40f9887771cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 20V, Negative-QTOF	splash10-000i-0739000000-b237198fe439874bfe9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 40V, Negative-QTOF	splash10-000l-9381000000-121882dcf0a220463e7e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 10V, Positive-QTOF	splash10-000i-0009000000-cdd50cb438363724f2fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 20V, Positive-QTOF	splash10-000i-0049000000-f3af8357287f194c7e63	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Demethylgriseofulvin 40V, Positive-QTOF	splash10-0f6t-5691000000-57d65aac2826a0cf04dd	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

141692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161302

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

Not Available

Showing metabocard for 6-Demethylgriseofulvin (HMDB0041813)

MOL for HMDB0041813 (6-Demethylgriseofulvin)

3D MOL for HMDB0041813 (6-Demethylgriseofulvin)

3D SDF for HMDB0041813 (6-Demethylgriseofulvin)

3D-SDF for HMDB0041813 (6-Demethylgriseofulvin)

PDB for HMDB0041813 (6-Demethylgriseofulvin)

3D PDB for HMDB0041813 (6-Demethylgriseofulvin)

SMILES for HMDB0041813 (6-Demethylgriseofulvin)

INCHI for HMDB0041813 (6-Demethylgriseofulvin)

Structure for HMDB0041813 (6-Demethylgriseofulvin)

3D Structure for HMDB0041813 (6-Demethylgriseofulvin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra