Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014544

Secondary Accession Numbers

HMDB14544

Metabolite Identification

Common Name

Griseofulvin

Description

Griseofulvin is only found in individuals that have used or taken this drug. It is an antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.

Structure

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

HMDB0014544
     RDKit          3D
Griseofulvin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3841   -3.1766    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397   -1.8578    0.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.9013    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -0.9695    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.0105    0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776   -0.1379    0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996    1.2708   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    0.8897   -1.1608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2432    2.1743   -1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488    0.1130   -0.4979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8116   -0.5453   -1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -0.4530   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -1.1536   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.4144   -2.4703 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8552   -0.8938   -0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -1.6305   -0.9840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2193   -1.3381   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174    0.0944    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836    0.8054    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.8095    1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    2.0968    2.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838    0.5198    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.1090    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972    2.1819    0.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982   -3.5699    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974   -3.2149   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988   -3.8557    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.7255    1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.7994    0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005    1.8924   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    0.2946   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989    2.4258   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197    3.0492   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    2.1526   -1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.0329   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1248   -1.4299    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5069   -0.2770   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351    0.3395    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018    2.9277    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    1.1854    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7808    2.4359    1.5151 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  6
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 10  3  1  0
 22 12  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

400
  Mrv0541 02231214392D          

 24 26  0  0  1  0            999 V2000
    5.4278    1.1433    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -0.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1782   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -0.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493   -3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707    1.1433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    2.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493   -0.8542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0348   -1.2667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0348   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819   -0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -1.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1618    0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8957    1.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6028    1.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    1.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790    1.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  8  2  1  6  0  0  0
  2 15  1  0  0  0  0
  3 12  1  0  0  0  0
  3 22  1  0  0  0  0
  4 11  2  0  0  0  0
  5 16  2  0  0  0  0
  6 18  1  0  0  0  0
  6 23  1  0  0  0  0
  7 21  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 10 16  1  0  0  0  0
 11 14  1  0  0  0  0
 12 17  2  0  0  0  0
 14 15  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014544

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

> <INCHI_KEY>
DDUHZTYCFQRHIY-RBHXEPJQSA-N

> <FORMULA>
C17H17ClO6

> <MOLECULAR_WEIGHT>
352.766

> <EXACT_MASS>
352.071365983

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.24576060438774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.172137458333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.68867051547463

> <JCHEM_PKA_STRONGEST_BASIC>
-4.322861287850263

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
87.8459

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
griseofulvin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014544
     RDKit          3D
Griseofulvin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3841   -3.1766    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397   -1.8578    0.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.9013    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -0.9695    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.0105    0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776   -0.1379    0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996    1.2708   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    0.8897   -1.1608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2432    2.1743   -1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488    0.1130   -0.4979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8116   -0.5453   -1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -0.4530   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -1.1536   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.4144   -2.4703 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8552   -0.8938   -0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -1.6305   -0.9840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2193   -1.3381   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174    0.0944    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836    0.8054    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.8095    1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    2.0968    2.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838    0.5198    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.1090    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972    2.1819    0.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982   -3.5699    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974   -3.2149   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988   -3.8557    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.7255    1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.7994    0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005    1.8924   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    0.2946   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989    2.4258   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197    3.0492   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    2.1526   -1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.0329   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1248   -1.4299    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5069   -0.2770   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351    0.3395    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018    2.9277    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    1.1854    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7808    2.4359    1.5151 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  6
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 10  3  1  0
 22 12  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 400                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      10.132   2.134   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.245  -0.690   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.666  -1.595   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.325  -0.112   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.999  -6.215   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.865   2.134   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.576   4.878   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.999  -1.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.665  -2.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.665  -3.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.753  -0.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.332  -2.365   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.148  -2.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.229   0.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.769   0.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.999  -4.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.332  -3.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.405   2.152   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.592   2.152   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.197   3.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.801   3.547   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.000  -2.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   3.459   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.811   6.215   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    8   15                                                       
CONECT    3   12   22                                                       
CONECT    4   11                                                            
CONECT    5   16                                                            
CONECT    6   18   23                                                       
CONECT    7   21   24                                                       
CONECT    8    2    9   11   12                                             
CONECT    9    8   10   13                                                  
CONECT   10    9   16                                                       
CONECT   11    4    8   14                                                  
CONECT   12    3    8   17                                                  
CONECT   13    9                                                            
CONECT   14   11   15   18                                                  
CONECT   15    2   14   19                                                  
CONECT   16    5   10   17                                                  
CONECT   17   12   16                                                       
CONECT   18    6   14   20                                                  
CONECT   19    1   15   21                                                  
CONECT   20   18   21                                                       
CONECT   21    7   19   20                                                  
CONECT   22    3                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0014544
HETATM    1  C1  UNL     1      -1.384  -3.177   0.424  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.240  -1.858   0.923  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.124  -0.901   0.447  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.370  -0.969   0.888  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.336   0.010   0.419  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.578  -0.138   0.460  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.800   1.271  -0.146  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.744   0.890  -1.161  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.243   2.174  -1.778  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.649   0.113  -0.498  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.812  -0.545  -1.431  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.477  -0.453  -0.947  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.652  -1.154  -1.253  1.00  0.00           C  
HETATM   14 CL1  UNL     1       1.597  -2.414  -2.470  1.00  0.00          CL  
HETATM   15  C11 UNL     1       2.855  -0.894  -0.636  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.004  -1.631  -0.984  1.00  0.00           O  
HETATM   17  C12 UNL     1       5.219  -1.338  -0.332  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.917   0.094   0.325  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.784   0.805   0.653  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.782   1.809   1.609  1.00  0.00           O  
HETATM   21  C15 UNL     1       3.009   2.097   2.259  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.584   0.520   0.012  1.00  0.00           C  
HETATM   23  C17 UNL     1      -0.737   1.109   0.168  1.00  0.00           C  
HETATM   24  O6  UNL     1      -0.997   2.182   0.726  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.398  -3.570   0.668  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.297  -3.215  -0.688  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.599  -3.856   0.818  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.716  -1.725   1.589  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.297   1.799   0.692  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.601   1.892  -0.596  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.187   0.295  -1.993  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.799   2.426  -2.713  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.420   3.049  -1.087  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.143   2.153  -1.946  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.999  -2.033  -0.717  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.125  -1.430   0.778  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.507  -0.277  -0.545  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.835   0.340   0.840  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.902   2.928   2.984  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.439   1.185   2.724  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.781   2.436   1.515  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   28
CONECT    5    6    6    7
CONECT    7    8   29   30
CONECT    8    9   10   31
CONECT    9   32   33   34
CONECT   10   11   23
CONECT   11   12
CONECT   12   13   13   22
CONECT   13   14   15
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   35   36   37
CONECT   18   19   38
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   39   40   41
CONECT   22   23
CONECT   23   24   24
END

HMDB0014544
     RDKit          3D
Griseofulvin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3841   -3.1766    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397   -1.8578    0.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.9013    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -0.9695    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.0105    0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776   -0.1379    0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996    1.2708   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    0.8897   -1.1608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2432    2.1743   -1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488    0.1130   -0.4979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8116   -0.5453   -1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -0.4530   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -1.1536   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.4144   -2.4703 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8552   -0.8938   -0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -1.6305   -0.9840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2193   -1.3381   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174    0.0944    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836    0.8054    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.8095    1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    2.0968    2.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838    0.5198    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.1090    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972    2.1819    0.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982   -3.5699    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974   -3.2149   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988   -3.8557    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156   -1.7255    1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.7994    0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005    1.8924   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    0.2946   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989    2.4258   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197    3.0492   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    2.1526   -1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.0329   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1248   -1.4299    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5069   -0.2770   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351    0.3395    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018    2.9277    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    1.1854    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7808    2.4359    1.5151 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  6
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 10  3  1  0
 22 12  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Griseofulvin	ChEBI
Amudane	ChEBI
Curling factor	ChEBI
Fulcin	ChEBI
Fulvicin	ChEBI
Grifulvin	ChEBI
Grisactin	ChEBI
Griseofulvina	ChEBI
Griseofulvine	ChEBI
Griseofulvinum	ChEBI
Grisovin	ChEBI
Grysio	ChEBI
Lamoryl	ChEBI
Likuden	ChEBI
Poncyl	ChEBI
Spirofulvin	ChEBI
Sporostatin	ChEBI
GRE	Kegg
Gris-peg	Kegg
Grisactin V	Kegg
Fulvicin u F	HMDB
Fulvicin-u-F	HMDB
GrisPEG	HMDB
Grifulvin V	HMDB
Gris peg	HMDB
Grisefuline	HMDB
V, Grifulvin	HMDB
FulvicinUF	HMDB

Chemical Formula

C₁₇H₁₇ClO₆

Average Molecular Weight

352.766

Monoisotopic Molecular Weight

352.071365983

IUPAC Name

(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

Traditional Name

griseofulvin

CAS Registry Number

126-07-8

SMILES

COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

InChI Identifier

InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

InChI Key

DDUHZTYCFQRHIY-RBHXEPJQSA-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
Alkyl aryl ether
Cyclohexenone
Aryl chloride
Aryl halide
Benzenoid
Vinylogous ester
Ketone
Cyclic ketone
Ether
Oxacycle
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

antibiotic antifungal drug (CHEBI:27779 )
organochlorine compound (CHEBI:27779 )
1-benzofurans (CHEBI:27779 )
oxaspiro compound (CHEBI:27779 )
benzofuran antifungal drug (CHEBI:27779 )
Other Polyketides (C06686 )
Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (C06686 )
Antibiotic fungicides (C06686 )
Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (LMPK13060001 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.05 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	178.628	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000946

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.85 m³·mol⁻¹	ChemAxon
Polarizability	34.25 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]+	179.613	30932474
DeepCCS	[M-H]-	177.217	30932474
DeepCCS	[M-2H]-	210.606	30932474
DeepCCS	[M+Na]+	185.751	30932474
AllCCS	[M+H]+	178.3	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	181.2	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.4	32859911
AllCCS	[M+HCOO]-	183.6	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.	7.85 minutes	32390414
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.	7.72 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5764 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2634.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	385.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	204.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	596.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	793.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1235.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.3 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	1683.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	442.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	401.3 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	54.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Griseofulvin	COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	3817.7	Standard polar	33892256
Griseofulvin	COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	2724.8	Standard non polar	33892256
Griseofulvin	COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC	2804.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	2636.3	Semi standard non polar	33892256
Griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	2563.8	Standard non polar	33892256
Griseofulvin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	3345.5	Standard polar	33892256
Griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	2848.9	Semi standard non polar	33892256
Griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	2774.9	Standard non polar	33892256
Griseofulvin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O	3430.1	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00400	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00400	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00400

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Griseofulvin

METLIN ID

Not Available

PubChem Compound

441140

PDB ID

Not Available

ChEBI ID

27779

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [PubMed:18505790 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Rasmussen BB, Jeppesen U, Gaist D, Brosen K: Griseofulvin and fluvoxamine interactions with the metabolism of theophylline. Ther Drug Monit. 1997 Feb;19(1):56-62. [PubMed:9029748 ]

Showing metabocard for Griseofulvin (HMDB0014544)

MOL for HMDB0014544 (Griseofulvin)

3D MOL for HMDB0014544 (Griseofulvin)

3D SDF for HMDB0014544 (Griseofulvin)

3D-SDF for HMDB0014544 (Griseofulvin)

PDB for HMDB0014544 (Griseofulvin)

3D PDB for HMDB0014544 (Griseofulvin)

SMILES for HMDB0014544 (Griseofulvin)

INCHI for HMDB0014544 (Griseofulvin)

Structure for HMDB0014544 (Griseofulvin)

3D Structure for HMDB0014544 (Griseofulvin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References