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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:15:15 UTC

Update Date

2022-03-07 02:53:44 UTC

HMDB ID

HMDB0033516

Secondary Accession Numbers

HMDB33516

Metabolite Identification

Common Name

Citreovirone

Description

Citreovirone belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Based on a literature review very few articles have been published on Citreovirone.

Structure

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

HMDB0033516
     RDKit          3D
Citreovirone
 32 32  0  0  0  0  0  0  0  0999 V2000
    5.0816   -1.6679    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668   -1.7220   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.5690   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    0.5886    0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718    1.7161    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2104    2.8274    1.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3863    1.6999    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    0.5566   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    0.4570   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.0088   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131   -0.2667    0.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -0.1751   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7113   -0.6685    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    0.2188    1.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656   -0.7261    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    0.8825   -0.2798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.1615   -1.4026    1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -0.5551   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.2952    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5483   -2.6913    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6927   -0.9913   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823    0.5889    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    3.7005    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465    2.5596    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    1.4800   -1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320   -0.2211   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    0.8248   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019   -0.8462   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270   -1.7047    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906    0.2495    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912   -1.3706   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518   -1.4679   -1.0934 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
M  END


  Mrv0541 05061307102D          

 18 18  0  0  0  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17 11  1  0  0  0  0
 18  1  1  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033516

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14Cl2O4/c1-18-10-4-7(2-8(15)5-10)3-9(16)6-11(17)12(13)14/h2,4-5,11-12,15,17H,3,6H2,1H3

> <INCHI_KEY>
ASUNQAFARHTUFP-UHFFFAOYSA-N

> <FORMULA>
C12H14Cl2O4

> <MOLECULAR_WEIGHT>
293.143

> <EXACT_MASS>
292.02691435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.771516471655055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.2921049080000007

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.134026701257888

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398174294896299

> <JCHEM_PKA_STRONGEST_BASIC>
-3.609208883243304

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.83

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033516
     RDKit          3D
Citreovirone
 32 32  0  0  0  0  0  0  0  0999 V2000
    5.0816   -1.6679    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668   -1.7220   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.5690   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    0.5886    0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718    1.7161    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2104    2.8274    1.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3863    1.6999    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    0.5566   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    0.4570   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.0088   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131   -0.2667    0.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -0.1751   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7113   -0.6685    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    0.2188    1.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656   -0.7261    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    0.8825   -0.2798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.1615   -1.4026    1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -0.5551   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.2952    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5483   -2.6913    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6927   -0.9913   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823    0.5889    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    3.7005    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465    2.5596    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    1.4800   -1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320   -0.2211   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    0.8248   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019   -0.8462   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270   -1.7047    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906    0.2495    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912   -1.3706   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518   -1.4679   -1.0934 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  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      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       8.002  -1.540   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0       6.668  -3.850   0.000  0.00  0.00          Cl+0
HETATM   15  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    7    8                                                       
CONECT    3    7    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   10                                                       
CONECT    6    9   11                                                       
CONECT    7    2    3    4                                                  
CONECT    8    2    5   15                                                  
CONECT    9    3    6   16                                                  
CONECT   10    4    5   18                                                  
CONECT   11    6   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0033516
HETATM    1  C1  UNL     1       5.082  -1.668   0.263  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.767  -1.722  -0.260  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.000  -0.569  -0.139  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.461   0.589   0.453  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.672   1.716   0.556  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.210   2.827   1.161  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.386   1.700   0.058  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.896   0.557  -0.540  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.467   0.457  -1.098  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.463  -0.009  -0.134  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.113  -0.267   0.999  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.890  -0.175  -0.502  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.711  -0.668   0.675  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.654   0.219   1.733  1.00  0.00           O  
HETATM   15  C11 UNL     1      -5.166  -0.726   0.223  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -5.735   0.882  -0.280  1.00  0.00          CL  
HETATM   17 CL2  UNL     1      -6.162  -1.403   1.525  1.00  0.00          CL  
HETATM   18  C12 UNL     1       1.704  -0.555  -0.631  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.117  -1.295   1.300  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.548  -2.691   0.279  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.693  -0.991  -0.358  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.482   0.589   0.844  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.759   3.700   1.302  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.747   2.560   0.122  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.711   1.480  -1.509  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.432  -0.221  -2.000  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.261   0.825  -0.804  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.002  -0.846  -1.365  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.427  -1.705   0.946  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.491   0.249   2.261  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.191  -1.371  -0.679  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.352  -1.468  -1.093  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   22
CONECT    5    6    7    7
CONECT    6   23
CONECT    7    8   24
CONECT    8    9   18   18
CONECT    9   10   25   26
CONECT   10   11   11   12
CONECT   12   13   27   28
CONECT   13   14   15   29
CONECT   14   30
CONECT   15   16   17   31
CONECT   18   32
END

HMDB0033516
     RDKit          3D
Citreovirone
 32 32  0  0  0  0  0  0  0  0999 V2000
    5.0816   -1.6679    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668   -1.7220   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.5690   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    0.5886    0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718    1.7161    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2104    2.8274    1.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3863    1.6999    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    0.5566   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    0.4570   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.0088   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131   -0.2667    0.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -0.1751   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7113   -0.6685    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    0.2188    1.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656   -0.7261    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    0.8825   -0.2798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.1615   -1.4026    1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -0.5551   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.2952    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5483   -2.6913    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6927   -0.9913   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823    0.5889    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    3.7005    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465    2.5596    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    1.4800   -1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320   -0.2211   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    0.8248   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019   -0.8462   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270   -1.7047    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906    0.2495    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912   -1.3706   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518   -1.4679   -1.0934 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,5-dichloro-4-Hydroxy-1-(3-hydroxy-5-methoxyphenyl)-2-pentanone, 9ci	HMDB

Chemical Formula

C₁₂H₁₄Cl₂O₄

Average Molecular Weight

293.143

Monoisotopic Molecular Weight

292.02691435

IUPAC Name

5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one

Traditional Name

5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one

CAS Registry Number

103955-67-5

SMILES

COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1

InChI Identifier

InChI=1S/C12H14Cl2O4/c1-18-10-4-7(2-8(15)5-10)3-9(16)6-11(17)12(13)14/h2,4-5,11-12,15,17H,3,6H2,1H3

InChI Key

ASUNQAFARHTUFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Beta-hydroxy ketone
Secondary alcohol
Chlorohydrin
Ketone
Halohydrin
Ether
Hydrocarbon derivative
Organohalogen compound
Organochloride
Carbonyl group
Organooxygen compound
Alkyl chloride
Alcohol
Organic oxide
Organic oxygen compound
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033516)
Cytoplasm (HMDB: HMDB0033516)

Source

Exogenous

Exogenous (HMDB: HMDB0033516)

Food

Food (HMDB: HMDB0033516)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033516)

Environmental role

Environmental contaminant (HMDB: HMDB0033516)

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	0.34 g/L	ALOGPS
logP	2.11	ALOGPS
logP	2.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.83 m³·mol⁻¹	ChemAxon
Polarizability	27.77 Å³	ChemAxon
Number of Rings	1	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]+	166.166	30932474
DeepCCS	[M-H]-	163.808	30932474
DeepCCS	[M-2H]-	196.694	30932474
DeepCCS	[M+Na]+	172.259	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	163.1	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	11.3019 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1775.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	292.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	121.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	512.3 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	444.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1013.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	384.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1191.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	352.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.3 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	56.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citreovirone	COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1	3867.5	Standard polar	33892256
Citreovirone	COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1	2230.3	Standard non polar	33892256
Citreovirone	COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1	2423.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citreovirone,1TMS,isomer #1	COC1=CC(O)=CC(CC(=O)CC(O[Si](C)(C)C)C(Cl)Cl)=C1	2330.8	Semi standard non polar	33892256
Citreovirone,1TMS,isomer #2	COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O[Si](C)(C)C)=C1	2330.6	Semi standard non polar	33892256
Citreovirone,1TMS,isomer #3	COC1=CC(O)=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C)=C1	2449.6	Semi standard non polar	33892256
Citreovirone,1TMS,isomer #4	COC1=CC(O)=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C)=C1	2472.2	Semi standard non polar	33892256
Citreovirone,2TMS,isomer #1	COC1=CC(CC(=O)CC(O[Si](C)(C)C)C(Cl)Cl)=CC(O[Si](C)(C)C)=C1	2348.4	Semi standard non polar	33892256
Citreovirone,2TMS,isomer #2	COC1=CC(O)=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=C1	2455.9	Semi standard non polar	33892256
Citreovirone,2TMS,isomer #3	COC1=CC(O)=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=C1	2432.4	Semi standard non polar	33892256
Citreovirone,2TMS,isomer #4	COC1=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2436.2	Semi standard non polar	33892256
Citreovirone,2TMS,isomer #5	COC1=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2448.9	Semi standard non polar	33892256
Citreovirone,3TMS,isomer #1	COC1=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2440.0	Semi standard non polar	33892256
Citreovirone,3TMS,isomer #1	COC1=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2264.5	Standard non polar	33892256
Citreovirone,3TMS,isomer #2	COC1=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2425.5	Semi standard non polar	33892256
Citreovirone,3TMS,isomer #2	COC1=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2371.6	Standard non polar	33892256
Citreovirone,1TBDMS,isomer #1	COC1=CC(O)=CC(CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)=C1	2586.4	Semi standard non polar	33892256
Citreovirone,1TBDMS,isomer #2	COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O[Si](C)(C)C(C)(C)C)=C1	2577.2	Semi standard non polar	33892256
Citreovirone,1TBDMS,isomer #3	COC1=CC(O)=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C1	2672.7	Semi standard non polar	33892256
Citreovirone,1TBDMS,isomer #4	COC1=CC(O)=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C1	2697.9	Semi standard non polar	33892256
Citreovirone,2TBDMS,isomer #1	COC1=CC(CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)=CC(O[Si](C)(C)C(C)(C)C)=C1	2809.2	Semi standard non polar	33892256
Citreovirone,2TBDMS,isomer #2	COC1=CC(O)=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C1	2909.4	Semi standard non polar	33892256
Citreovirone,2TBDMS,isomer #3	COC1=CC(O)=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C1	2873.8	Semi standard non polar	33892256
Citreovirone,2TBDMS,isomer #4	COC1=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2878.6	Semi standard non polar	33892256
Citreovirone,2TBDMS,isomer #5	COC1=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2870.9	Semi standard non polar	33892256
Citreovirone,3TBDMS,isomer #1	COC1=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	3138.3	Semi standard non polar	33892256
Citreovirone,3TBDMS,isomer #1	COC1=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2838.6	Standard non polar	33892256
Citreovirone,3TBDMS,isomer #2	COC1=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	3096.6	Semi standard non polar	33892256
Citreovirone,3TBDMS,isomer #2	COC1=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	3013.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ll-7920000000-9d32481b8e90d2101631	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirone GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9222100000-ff1d67cd45750a32a44f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirone 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 - Citreovirone 10V, Positive-QTOF	splash10-004l-0290000000-9ce95f3e076bacea4f1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 20V, Positive-QTOF	splash10-014i-0930000000-b9cd6f93428f0ea4906c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 40V, Positive-QTOF	splash10-03di-0910000000-e0c00e5d4b24ab01cb77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 10V, Negative-QTOF	splash10-002f-0790000000-c0bda84e06f686b54293	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 20V, Negative-QTOF	splash10-0c2c-0790000000-a03e883c8bf1233c44b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 40V, Negative-QTOF	splash10-05ic-2920000000-083fd83365c98944ba0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 10V, Negative-QTOF	splash10-000i-0960000000-a91e987a3a06a257920f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 20V, Negative-QTOF	splash10-000i-3900000000-b9f7110002d5664304e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 40V, Negative-QTOF	splash10-00dr-3900000000-70c24cd23b12ee9a9bf0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 10V, Positive-QTOF	splash10-0006-0090000000-033cac2014bed5341651	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 20V, Positive-QTOF	splash10-000i-0590000000-0eb58989bb5505afe1ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirone 40V, Positive-QTOF	splash10-059i-4900000000-fac642c742aba9126636	2021-09-22	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

FDB011571

KNApSAcK ID

C00055274

Chemspider ID

35013620

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102115407

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Citreovirone (HMDB0033516)

MOL for HMDB0033516 (Citreovirone)

3D MOL for HMDB0033516 (Citreovirone)

3D SDF for HMDB0033516 (Citreovirone)

3D-SDF for HMDB0033516 (Citreovirone)

PDB for HMDB0033516 (Citreovirone)

3D PDB for HMDB0033516 (Citreovirone)

SMILES for HMDB0033516 (Citreovirone)

INCHI for HMDB0033516 (Citreovirone)

Structure for HMDB0033516 (Citreovirone)

3D Structure for HMDB0033516 (Citreovirone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra