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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 03:36:37 UTC

Update Date

2022-03-07 02:57:08 UTC

HMDB ID

HMDB0041691

Secondary Accession Numbers

HMDB41691

Metabolite Identification

Common Name

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone

Description

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety. 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone.

Structure

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

HMDB0041691
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.2711    2.4617    1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    1.6337    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.9447   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411   -0.3333   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028    0.1133   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459   -1.0308   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882   -0.7153    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.9686   -0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -0.6385   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8689   -0.9130   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.0579    0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    0.2622    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838    0.1984    1.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421    0.7906    2.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.1331    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548    1.1972    0.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9736    1.5361   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965    0.6635   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -1.0266   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.7658   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    0.3297   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137   -1.9045   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -1.2804    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -1.4263   -1.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358   -0.6826   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8363    0.6848    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.9763    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0842    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16  2  1  0
 15  7  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
M  END


  Mrv1652302151909352D          

 16 17  0  0  0  0            999 V2000
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041691

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c12-8-4-6(5-9(13)11(8)15)3-7-1-2-10(14)16-7/h4-5,7,12-13,15H,1-3H2

> <INCHI_KEY>
CZVAQLJEUUFQCH-UHFFFAOYSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.21

> <EXACT_MASS>
224.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.64014855580242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.311756733

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.188142139347566

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.887604081092672

> <JCHEM_PKA_STRONGEST_BASIC>
-6.002982729000778

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
55.2886

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041691
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.2711    2.4617    1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    1.6337    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.9447   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411   -0.3333   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028    0.1133   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459   -1.0308   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882   -0.7153    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.9686   -0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -0.6385   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8689   -0.9130   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.0579    0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    0.2622    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838    0.1984    1.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421    0.7906    2.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.1331    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548    1.1972    0.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9736    1.5361   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965    0.6635   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -1.0266   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.7658   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    0.3297   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137   -1.9045   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -1.2804    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -1.4263   -1.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358   -0.6826   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8363    0.6848    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.9763    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0842    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16  2  1  0
 15  7  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
M  END

HEADER    PROTEIN                                 15-FEB-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-FEB-19         0                                  
HETATM    1  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.127  -6.041   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.556  -3.330   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.137  -0.885   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.469   3.735   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12                                                            
CONECT   15   11                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0041691
HETATM    1  O1  UNL     1      -3.271   2.462   1.176  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.955   1.634   0.281  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.806   0.945  -0.720  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.041  -0.333  -0.954  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.603   0.113  -0.804  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.846  -1.031  -0.171  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.588  -0.715   0.030  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.572  -0.969  -0.903  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.900  -0.639  -0.630  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.869  -0.913  -1.607  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.257  -0.058   0.565  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.605   0.262   0.808  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.284   0.198   1.501  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.642   0.791   2.722  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.976  -0.133   1.217  1.00  0.00           C  
HETATM   16  O5  UNL     1      -1.655   1.197   0.070  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.974   1.536  -1.628  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.796   0.664  -0.323  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.299  -1.027  -0.132  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.240  -0.766  -1.955  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.128   0.330  -1.779  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.914  -1.905  -0.870  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.281  -1.280   0.815  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.301  -1.426  -1.849  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.836  -0.683  -1.431  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.836   0.685   1.688  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.921   0.976   3.406  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.222   0.084   1.986  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   16   21
CONECT    6    7   22   23
CONECT    7    8    8   15
CONECT    8    9   24
CONECT    9   10   11   11
CONECT   10   25
CONECT   11   12   13
CONECT   12   26
CONECT   13   14   15   15
CONECT   14   27
CONECT   15   28
END

HMDB0041691
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.2711    2.4617    1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    1.6337    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.9447   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411   -0.3333   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028    0.1133   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459   -1.0308   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882   -0.7153    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.9686   -0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -0.6385   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8689   -0.9130   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.0579    0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    0.2622    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838    0.1984    1.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421    0.7906    2.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.1331    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548    1.1972    0.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9736    1.5361   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965    0.6635   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -1.0266   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.7658   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    0.3297   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137   -1.9045   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -1.2804    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -1.4263   -1.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358   -0.6826   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8363    0.6848    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.9763    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.0842    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16  2  1  0
 15  7  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactone	Generator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone	Generator

Chemical Formula

C₁₁H₁₂O₅

Average Molecular Weight

224.21

Monoisotopic Molecular Weight

224.068473494

IUPAC Name

5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one

Traditional Name

5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O

InChI Identifier

InChI=1S/C11H12O5/c12-8-4-6(5-9(13)11(8)15)3-7-1-2-10(14)16-7/h4-5,7,12-13,15H,1-3H2

InChI Key

CZVAQLJEUUFQCH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Benzenetriols and derivatives

Direct Parent

Pyrogallols and derivatives

Alternative Parents

Substituents

Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 12184788)

Cellular substructure

Extracellular (HMDB: HMDB0041691)
Cytoplasm (HMDB: HMDB0041691)

Source

Exogenous

Exogenous (HMDB: HMDB0041691)

Food

Food (HMDB: HMDB0041691)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041691)

Tea

Tea products (HMDB: HMDB0041691)

Nut

Nuts (HMDB: HMDB0041691)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041691)

Fruit

Berries (HMDB: HMDB0041691)

Pome

Apple (HMDB: HMDB0041691)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041691)

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	1.94 g/L	ALOGPS
logP	1.18	ALOGPS
logP	1.31	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.29 m³·mol⁻¹	ChemAxon
Polarizability	21.64 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]+	152.546	31661259
DarkChem	[M-H]-	151.238	31661259
DeepCCS	[M+H]+	149.529	30932474
DeepCCS	[M-H]-	147.171	30932474
DeepCCS	[M-2H]-	181.625	30932474
DeepCCS	[M+Na]+	156.096	30932474
AllCCS	[M+H]+	150.9	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	150.3	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	150.5	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.	3.34 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2147 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1330.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	256.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	476.5 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	362.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	440.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	747.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	319.3 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	1065.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	508.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	303.2 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	281.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O	3813.3	Standard polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O	2334.7	Standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O	2452.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O	2229.9	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #2	C[Si](C)(C)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O	2229.6	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1O	2260.0	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O[Si](C)(C)C	2268.8	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,3TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2314.8	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O	2514.1	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O	2513.1	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O	2790.2	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C	2758.5	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3020.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbi-4900000000-aa407ce8b92827122435	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone GC-MS (3 TMS) - 70eV, Positive	splash10-00us-4009100000-3c85a877af2785527a37	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 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 - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Positive-QTOF	splash10-004i-0390000000-005c046b64fa400546ea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Positive-QTOF	splash10-004r-2920000000-3da2123cba34d8e561f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Positive-QTOF	splash10-000i-9800000000-4d0ddda730f3f457928c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Negative-QTOF	splash10-00di-0290000000-ca50e6c2cd8c6aed9f93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Negative-QTOF	splash10-00fs-2970000000-91fdf1beca5ad48fa42f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Negative-QTOF	splash10-004l-7900000000-06a574a6947ca4bd6f67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Positive-QTOF	splash10-004u-1950000000-176b5d1849bbdc3eaa1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Positive-QTOF	splash10-05a9-4910000000-3bce2f7fdb3f916695a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Positive-QTOF	splash10-05o9-9600000000-dbc584e157afb6b9dbed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Negative-QTOF	splash10-00di-1690000000-fbe999d62045de96f6ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Negative-QTOF	splash10-0f7t-8910000000-8bd6afb0fb725a6e3ec6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Negative-QTOF	splash10-0fk9-6900000000-a243697def0606ce40ee	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 984	12184788	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 984	10725114	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 984	20080030	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 984	18433082	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FDB029854

KNApSAcK ID

Not Available

Chemspider ID

21233624

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44389277

PDB ID

Not Available

ChEBI ID

134255

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,3-dihydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate	details

Showing metabocard for 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone (HMDB0041691)

MOL for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

3D MOL for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

3D SDF for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

3D-SDF for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

PDB for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

3D PDB for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

SMILES for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

INCHI for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

Structure for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

3D Structure for HMDB0041691 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions