Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:15:12 UTC

Update Date

2022-03-07 02:53:44 UTC

HMDB ID

HMDB0033515

Secondary Accession Numbers

HMDB33515

Metabolite Identification

Common Name

Citreovirenone

Description

Citreovirenone 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 Citreovirenone.

Structure

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

HMDB0033515
     RDKit          3D
Citreovirenone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1616   -1.6214    0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454   -1.5239    1.1804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.4593    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    0.4655   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    1.5121   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    2.4109   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    1.6246   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446    0.7378    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.9471    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2725    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -0.4719   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723   -1.1083   -1.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -1.5980   -2.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.1517   -0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8515    0.1838   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1227    0.2041    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7805    0.4184    0.7232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.2942    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.6493   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7624   -0.6984    0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6970   -2.5046    1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738    0.3356   -0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    2.2332   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    2.4556   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    0.5661    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.0439    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.6007   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -1.9501   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -1.4170   -1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.9428   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287   -0.7861    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933    0.9752    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414    0.4903    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.9845    1.8754 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
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
 17 10  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
 11 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 34  1  0
M  END

  Mrv0541 05061307102D          

 18 19  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033515

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O4/c1-9-3-11(15)8-14(18-9)6-10-4-12(16)7-13(5-10)17-2/h4-5,7-9,16H,3,6H2,1-2H3

> <INCHI_KEY>
WMCPLZDBHVOXCJ-UHFFFAOYSA-N

> <FORMULA>
C14H16O4

> <MOLECULAR_WEIGHT>
248.2744

> <EXACT_MASS>
248.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.837625398203304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(3-hydroxy-5-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-2H-pyran-4-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.0073336743333337

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.52910476931398

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.400990691066466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.511398919741771

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
69.01270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-hydroxy-5-methoxyphenyl)methyl]-6-methyl-5,6-dihydropyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033515
     RDKit          3D
Citreovirenone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1616   -1.6214    0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454   -1.5239    1.1804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.4593    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    0.4655   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    1.5121   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    2.4109   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    1.6246   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446    0.7378    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.9471    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2725    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -0.4719   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723   -1.1083   -1.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -1.5980   -2.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.1517   -0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8515    0.1838   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1227    0.2041    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7805    0.4184    0.7232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.2942    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.6493   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7624   -0.6984    0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6970   -2.5046    1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738    0.3356   -0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    2.2332   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    2.4556   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    0.5661    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.0439    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.6007   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -1.9501   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -1.4170   -1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.9428   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287   -0.7861    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933    0.9752    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414    0.4903    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.9845    1.8754 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
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
 17 10  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
 11 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 34  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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   17                                                            
CONECT    3    9   11                                                       
CONECT    4   10   12                                                       
CONECT    5   10   13                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8   11   14                                                       
CONECT    9    1    3   18                                                  
CONECT   10    4    5    6                                                  
CONECT   11    3    8   15                                                  
CONECT   12    4    7   16                                                  
CONECT   13    5    7   17                                                  
CONECT   14    6    8   18                                                  
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17    2   13                                                       
CONECT   18    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0033515
HETATM    1  C1  UNL     1      -5.162  -1.621   0.677  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.845  -1.524   1.180  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.064  -0.459   0.718  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.539   0.466  -0.190  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.773   1.512  -0.645  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.318   2.411  -1.564  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.486   1.625  -0.166  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.945   0.738   0.743  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.437   0.947   1.190  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.446   0.272   0.369  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.188  -0.472  -0.694  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.272  -1.108  -1.454  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.059  -1.598  -2.593  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.622  -1.152  -0.832  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.851   0.184  -0.171  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.123   0.204   0.647  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.781   0.418   0.723  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.757  -0.294   1.167  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.064  -1.649  -0.444  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.762  -0.698   0.897  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.697  -2.505   1.051  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.574   0.336  -0.545  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.223   2.233  -2.542  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.878   2.456  -0.527  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.560   0.566   2.245  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.614   2.044   1.249  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.155  -0.601  -0.991  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.652  -1.950  -0.041  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.406  -1.417  -1.559  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.888   0.943  -0.993  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.629  -0.786   0.629  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.793   0.975   0.215  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.941   0.490   1.707  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.331  -0.985   1.875  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   17
CONECT   11   12   27
CONECT   12   13   13   14
CONECT   14   15   28   29
CONECT   15   16   17   30
CONECT   16   31   32   33
CONECT   18   34
END

HMDB0033515
     RDKit          3D
Citreovirenone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1616   -1.6214    0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454   -1.5239    1.1804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.4593    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    0.4655   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    1.5121   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    2.4109   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    1.6246   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446    0.7378    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.9471    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2725    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -0.4719   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723   -1.1083   -1.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -1.5980   -2.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.1517   -0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8515    0.1838   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1227    0.2041    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7805    0.4184    0.7232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.2942    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.6493   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7624   -0.6984    0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6970   -2.5046    1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738    0.3356   -0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    2.2332   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    2.4556   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    0.5661    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.0439    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.6007   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -1.9501   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -1.4170   -1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.9428   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287   -0.7861    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933    0.9752    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414    0.4903    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.9845    1.8754 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
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  2  0
 18  3  1  0
 17 10  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
 11 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₄

Average Molecular Weight

248.2744

Monoisotopic Molecular Weight

248.104859

IUPAC Name

6-[(3-hydroxy-5-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-2H-pyran-4-one

Traditional Name

2-[(3-hydroxy-5-methoxyphenyl)methyl]-6-methyl-5,6-dihydropyran-4-one

CAS Registry Number

103955-68-6

SMILES

COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1

InChI Identifier

InChI=1S/C14H16O4/c1-9-3-11(15)8-14(18-9)6-10-4-12(16)7-13(5-10)17-2/h4-5,7-9,16H,3,6H2,1-2H3

InChI Key

WMCPLZDBHVOXCJ-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
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Dihydropyranone
Monocyclic benzene moiety
Vinylogous ester
Ketone
Cyclic ketone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033515)
Cytoplasm (HMDB: HMDB0033515)

Source

Exogenous

Exogenous (HMDB: HMDB0033515)

Food

Food (HMDB: HMDB0033515)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033515)

Environmental role

Environmental contaminant (HMDB: HMDB0033515)

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	3091 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.01	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.01 m³·mol⁻¹	ChemAxon
Polarizability	25.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.342	31661259
DarkChem	[M-H]-	162.179	31661259
DeepCCS	[M+H]+	165.348	30932474
DeepCCS	[M-H]-	162.99	30932474
DeepCCS	[M-2H]-	195.877	30932474
DeepCCS	[M+Na]+	171.442	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.6	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citreovirenone	COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1	3358.9	Standard polar	33892256
Citreovirenone	COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1	2180.7	Standard non polar	33892256
Citreovirenone	COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1	2338.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citreovirenone,1TMS,isomer #1	COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O[Si](C)(C)C)=C1	2268.0	Semi standard non polar	33892256
Citreovirenone,1TMS,isomer #2	COC1=CC(O)=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=C1	2223.4	Semi standard non polar	33892256
Citreovirenone,2TMS,isomer #1	COC1=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C)=C1	2251.3	Semi standard non polar	33892256
Citreovirenone,2TMS,isomer #1	COC1=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C)=C1	2290.5	Standard non polar	33892256
Citreovirenone,1TBDMS,isomer #1	COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1	2521.2	Semi standard non polar	33892256
Citreovirenone,1TBDMS,isomer #2	COC1=CC(O)=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=C1	2507.6	Semi standard non polar	33892256
Citreovirenone,2TBDMS,isomer #1	COC1=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1	2727.1	Semi standard non polar	33892256
Citreovirenone,2TBDMS,isomer #1	COC1=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1	2705.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-5960000000-ab51728ea87161d891d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirenone GC-MS (1 TMS) - 70eV, Positive	splash10-0c03-5192000000-d718708a04526b734f49	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreovirenone 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 - Citreovirenone 10V, Positive-QTOF	splash10-0002-0190000000-cac62387d88dc62f899f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 20V, Positive-QTOF	splash10-0002-8970000000-a73791477d8271986a13	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 40V, Positive-QTOF	splash10-00kf-9810000000-c877424da9df433c8214	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 10V, Negative-QTOF	splash10-0002-0090000000-f5a401a1366b05ecbd48	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 20V, Negative-QTOF	splash10-0002-2390000000-714ccf78a03070a5e699	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 40V, Negative-QTOF	splash10-0543-9410000000-7a428ee4efa7429c1d1a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 10V, Positive-QTOF	splash10-000b-0790000000-b81ab49381e8f49186c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 20V, Positive-QTOF	splash10-053j-4930000000-69e480cdea1d45901b31	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 40V, Positive-QTOF	splash10-0a4s-5910000000-81477cfb09dbe01cc92a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 10V, Negative-QTOF	splash10-0002-0490000000-d0b16d17c36b9607d91d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 20V, Negative-QTOF	splash10-007a-5950000000-c5042f4390a027086203	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreovirenone 40V, Negative-QTOF	splash10-000e-3920000000-efc0126c898b32ac98db	2021-09-24	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

FDB011570

KNApSAcK ID

C00055273

Chemspider ID

35013619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751444

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836321

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 Citreovirenone (HMDB0033515)

MOL for HMDB0033515 (Citreovirenone)

3D MOL for HMDB0033515 (Citreovirenone)

3D SDF for HMDB0033515 (Citreovirenone)

3D-SDF for HMDB0033515 (Citreovirenone)

PDB for HMDB0033515 (Citreovirenone)

3D PDB for HMDB0033515 (Citreovirenone)

SMILES for HMDB0033515 (Citreovirenone)

INCHI for HMDB0033515 (Citreovirenone)

Structure for HMDB0033515 (Citreovirenone)

3D Structure for HMDB0033515 (Citreovirenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra