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Showing metabocard for Isohomovanillic acid (HMDB0000333)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:43 UTC
HMDB IDHMDB0000333
Secondary Accession Numbers
  • HMDB00333
Metabolite Identification
Common NameIsohomovanillic acid
DescriptionIsohomovanillic acid, also known as homoisovanillate, 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. Isohomovanillic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make isohomovanillic acid a potential biomarker for the consumption of these foods. Isohomovanillic acid 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 small amount of articles have been published on Isohomovanillic acid.
Structure
Data?1676999683
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000333 (Isohomovanillic acid)

3-Hydroxy-4-methoxyphenylacetic acid.mol
  Mrv0541 02231218272D          

 13 13  0  0  0  0            999 V2000
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
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3D MOL for HMDB0000333 (Isohomovanillic acid)

HMDB0000333
     RDKit          3D
Isohomovanillic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.8480    0.5214    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9830   -0.5257   -0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.3160   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    0.9412    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157    1.0751    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388    0.0117   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    0.2438   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    0.0160    0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -0.3447    1.9874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352    0.2115    0.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519   -1.2124   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098   -1.3828   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678   -2.6125   -0.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538    1.2238   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    0.0823    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.1026    1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188    1.7429    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568    2.0502    0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7703    1.3041   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888   -0.4120   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.1271    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737   -2.0434   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503   -2.8041   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
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3D SDF for HMDB0000333 (Isohomovanillic acid)

3-Hydroxy-4-methoxyphenylacetic acid.mol
  Mrv0541 02231218272D          

 13 13  0  0  0  0            999 V2000
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000333

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CC(O)=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)

> <INCHI_KEY>
BWXLCOBSWMQCGP-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.719256927378964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
1.1497575179999997

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.910032800229548

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.744853115039856

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890936914925856

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
45.8097

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isohomovanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000333 (Isohomovanillic acid)

HMDB0000333
     RDKit          3D
Isohomovanillic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.8480    0.5214    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9830   -0.5257   -0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.3160   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    0.9412    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157    1.0751    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388    0.0117   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    0.2438   -0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    0.0160    0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -0.3447    1.9874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352    0.2115    0.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519   -1.2124   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098   -1.3828   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678   -2.6125   -0.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538    1.2238   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    0.0823    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.1026    1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188    1.7429    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568    2.0502    0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7703    1.3041   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888   -0.4120   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.1271    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737   -2.0434   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503   -2.8041   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0000333 (Isohomovanillic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Hydroxy-4-methoxyphenylacetic acid.mol          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11   12    8                                                       
CONECT   12   11                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0000333 (Isohomovanillic acid)

COMPND    HMDB0000333
HETATM    1  C1  UNL     1       3.848   0.521   0.163  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.983  -0.526  -0.157  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.613  -0.316  -0.201  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.060   0.941   0.071  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.316   1.075   0.007  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.139   0.012  -0.314  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.585   0.244  -0.358  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.261   0.016   0.926  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.693  -0.345   1.987  1.00  0.00           O  
HETATM   10  O3  UNL     1      -4.635   0.212   0.980  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.552  -1.212  -0.575  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.810  -1.383  -0.522  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.368  -2.612  -0.786  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.854   1.224  -0.716  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.869   0.082   0.296  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.521   1.103   1.029  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.719   1.743   0.315  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.757   2.050   0.217  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.770   1.304  -0.646  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.089  -0.412  -1.124  1.00  0.00           H  
HETATM   21  H8  UNL     1      -5.025   1.127   0.731  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.174  -2.043  -0.824  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.350  -2.804  -0.765  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   11
CONECT    7    8   19   20
CONECT    8    9    9   10
CONECT   10   21
CONECT   11   12   12   22
CONECT   12   13
CONECT   13   23
END
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SMILES for HMDB0000333 (Isohomovanillic acid)

COC1=CC=C(CC(O)=O)C=C1O
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INCHI for HMDB0000333 (Isohomovanillic acid)

InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Homoisovanillic acidChEBI
HomoisovanillateGenerator
IsohomovanillateGenerator
3-Hydroxy-4-methoxyphenylacetateHMDB
3-Hydroxy-4-methoxyphenylacetic acidHMDB
4-Methoxy-3-hydroxyphenylacetateHMDB
4-Methoxy-3-hydroxyphenylacetic acidHMDB
Homo-iso-vanillic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-(3-hydroxy-4-methoxyphenyl)acetic acid
Traditional Nameisohomovanillic acid
CAS Registry Number1131-94-8
SMILES
COC1=CC=C(CC(O)=O)C=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyBWXLCOBSWMQCGP-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.64 g/LALOGPS
logP0.88ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m³·mol⁻¹ChemAxon
Polarizability17.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.14831661259
DarkChem[M-H]-141.02131661259
AllCCS[M+H]+139.44532859911
AllCCS[M-H]-138.12932859911
DeepCCS[M+H]+138.37530932474
DeepCCS[M-H]-135.65130932474
DeepCCS[M-2H]-172.07130932474
DeepCCS[M+Na]+147.37430932474
AllCCS[M+H]+139.432859911
AllCCS[M+H-H2O]+135.232859911
AllCCS[M+NH4]+143.432859911
AllCCS[M+Na]+144.532859911
AllCCS[M-H]-138.132859911
AllCCS[M+Na-2H]-139.032859911
AllCCS[M+HCOO]-140.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.3.31 minutes32390414
Predicted by Siyang on May 30, 20229.7675 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.76 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1225.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid300.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid104.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid169.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid67.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid373.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid303.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)124.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid761.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid312.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid959.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid214.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid289.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate470.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA272.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water208.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isohomovanillic acidCOC1=CC=C(CC(O)=O)C=C1O3086.9Standard polar33892256
Isohomovanillic acidCOC1=CC=C(CC(O)=O)C=C1O1654.7Standard non polar33892256
Isohomovanillic acidCOC1=CC=C(CC(O)=O)C=C1O1688.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isohomovanillic acid,1TMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C)C=C1O1729.4Semi standard non polar33892256
Isohomovanillic acid,1TMS,isomer #2COC1=CC=C(CC(=O)O)C=C1O[Si](C)(C)C1793.4Semi standard non polar33892256
Isohomovanillic acid,2TMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C1789.1Semi standard non polar33892256
Isohomovanillic acid,1TBDMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C1O1964.0Semi standard non polar33892256
Isohomovanillic acid,1TBDMS,isomer #2COC1=CC=C(CC(=O)O)C=C1O[Si](C)(C)C(C)(C)C2034.4Semi standard non polar33892256
Isohomovanillic acid,2TBDMS,isomer #1COC1=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2253.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2900000000-4e352872bb3470aa81362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (2 TMS) - 70eV, Positivesplash10-01w0-9352000000-143f546e1228ddc2e7152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isohomovanillic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 10V, Positive-QTOFsplash10-014i-0900000000-91acb75622a4c8f430d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 20V, Positive-QTOFsplash10-000i-0900000000-a125f1e015a1c73b12ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 40V, Positive-QTOFsplash10-00dj-9800000000-f5d1b07059db50410c4f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 10V, Negative-QTOFsplash10-001r-0900000000-ef1cc468bfa35cfd42d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 20V, Negative-QTOFsplash10-01qi-0900000000-4db0068faa20425768682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 40V, Negative-QTOFsplash10-0abc-6900000000-023c60c5b54990926d1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 10V, Negative-QTOFsplash10-0080-0900000000-d7c6c45f6ff0ccf82daa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 20V, Negative-QTOFsplash10-00di-2900000000-a7c52faea7b28da21c5b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 40V, Negative-QTOFsplash10-00dl-9600000000-9c2c0716135d0670d6a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 10V, Positive-QTOFsplash10-000i-0900000000-b7aa6eaaa67f8542dca32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 20V, Positive-QTOFsplash10-000i-2900000000-8b26408527af31965af02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isohomovanillic acid 40V, Positive-QTOFsplash10-0ktr-9400000000-ca087049a04403bc95022021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Parkinson's Disease		 details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Ebinger G, Adriaenssens K: Iso-homovanillic acid determination in cerebrospinal fluid and in urine during L-DOPA treatment of Parkinson's disease. Clin Chim Acta. 1973 Nov 15;48(4):427-31. [PubMed:4761590 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021958
KNApSAcK IDNot Available
Chemspider ID141092
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5322
PubChem Compound160562
PDB IDNot Available
ChEBI ID70818
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHarlay, Victor. Synthesis of homoisovanillic acid. New method for the preparation of homoveratric acid. Compt. rend. (1946), 223 675-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of 4-O-methylated catecholamine metabolites in urine by mass fragmentography. Clin Chem. 1979 Oct;25(10):1708-13. [PubMed:476919 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77