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Showing metabocard for Homovanillin (HMDB0005175)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-31 13:02:28 UTC
Update Date2023-02-21 17:17:06 UTC
HMDB IDHMDB0005175
Secondary Accession Numbers
  • HMDB05175
Metabolite Identification
Common NameHomovanillin
DescriptionHomovanillin, also known as HMPAL, 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. Homovanillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Homovanillin exists in all living organisms, ranging from bacteria to humans. Within humans, homovanillin participates in a number of enzymatic reactions. In particular, homovanillin can be converted into p-hydroxyphenylacetic acid through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, homovanillin can be biosynthesized from tyramine through its interaction with the enzyme amiloride-sensitive amine oxidase [copper-containing]. In humans, homovanillin is involved in the metabolic disorder called tyrosinemia type I. Homovanillin is a floral and vanilla tasting compound. Outside of the human body,.
Structure
Data?1676999826
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005175 (Homovanillin)


  Mrv0541 02231220212D          

 12 12  0  0  0  0            999 V2000
   15.1533  -12.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7242  -13.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -16.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5821  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1533  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1533  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4387  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4387  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5821  -15.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -11.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for HMDB0005175 (Homovanillin)

HMDB0005175
     RDKit          3D
Homovanillin
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.0608    1.7798    1.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533    0.5924    0.7163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2908   -0.1335    0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    0.2816    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -0.4344   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    0.0294    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938    0.9183   -1.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565    1.1883   -1.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -1.5901   -0.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4910   -2.0264   -0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -1.2984   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8591   -1.6830   -0.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    1.5864    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    2.5278    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0463    2.2507    1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2526    1.1960    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679   -0.8391    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6038    0.5813    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    1.3296   -0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476   -2.1503   -1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053   -2.9308   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434   -1.1758   -0.2960 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
  6  7  1  0
  7  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0005175 (Homovanillin)


  Mrv0541 02231220212D          

 12 12  0  0  0  0            999 V2000
   15.1533  -12.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7242  -13.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -16.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5821  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1533  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1533  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4387  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4387  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5821  -15.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8677  -11.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005175

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3

> <INCHI_KEY>
GOQGGGANVKPMNH-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.814925287007217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
0.9911412656666663

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.359998305844062

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.9388836349945

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8894177024457335

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
44.8843

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homovanillin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0005175 (Homovanillin)

HMDB0005175
     RDKit          3D
Homovanillin
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.0608    1.7798    1.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533    0.5924    0.7163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2908   -0.1335    0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    0.2816    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -0.4344   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    0.0294    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938    0.9183   -1.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565    1.1883   -1.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -1.5901   -0.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4910   -2.0264   -0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -1.2984   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8591   -1.6830   -0.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    1.5864    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    2.5278    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0463    2.2507    1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2526    1.1960    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679   -0.8391    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6038    0.5813    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    1.3296   -0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476   -2.1503   -1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053   -2.9308   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434   -1.1758   -0.2960 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
  6  7  1  0
  7  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0005175 (Homovanillin)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      28.286 -23.129   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      25.618 -24.669   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.620 -30.059   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      29.620 -26.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.620 -25.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.953 -27.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.286 -24.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.286 -27.749   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.952 -25.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.952 -26.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.953 -29.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.620 -22.359   0.000  0.00  0.00           C+0
CONECT    1    7   12                                                       
CONECT    2    9                                                            
CONECT    3   11                                                            
CONECT    4    5    6    8                                                  
CONECT    5    4    7                                                       
CONECT    6    4   11                                                       
CONECT    7    1    5    9                                                  
CONECT    8    4   10                                                       
CONECT    9    2    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    3    6                                                       
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0005175 (Homovanillin)

COMPND    HMDB0005175
HETATM    1  C1  UNL     1      -2.061   1.780   1.426  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.353   0.592   0.716  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.291  -0.133   0.217  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.030   0.282   0.401  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.101  -0.434  -0.093  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.498   0.029   0.117  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.894   0.918  -1.020  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.156   1.188  -1.943  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.811  -1.590  -0.784  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.491  -2.026  -0.982  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.544  -1.298  -0.481  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.859  -1.683  -0.647  1.00  0.00           O  
HETATM   13  H1  UNL     1      -1.538   1.586   2.373  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.536   2.528   0.787  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.046   2.251   1.684  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.253   1.196   0.948  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.168  -0.839   0.178  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.604   0.581   1.078  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.906   1.330  -0.986  1.00  0.00           H  
HETATM   20  H8  UNL     1       1.648  -2.150  -1.170  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.705  -2.931  -1.523  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.643  -1.176  -0.296  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    9    9
CONECT    6    7   17   18
CONECT    7    8    8   19
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   11   12
CONECT   12   22
END
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SMILES for HMDB0005175 (Homovanillin)

COC1=C(O)C=CC(CC=O)=C1
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INCHI for HMDB0005175 (Homovanillin)

InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Methoxy-4-hydroxyphenylacetaldehydeChEBI
4-Hydroxy-3-methoxybenzeneacetaldehydeChEBI
HMPALChEBI
(4-Hydroxy-3-methoxyphenyl)acetaldehydeKegg
2-(4-Hydroxy-3-methoxyphenyl) ethanalHMDB
4-Hydroxy-3-methoxy-benzeneacetaldehydeHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional Namehomovanillin
CAS Registry Number5703-24-2
SMILES
COC1=C(O)C=CC(CC=O)=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3
InChI KeyGOQGGGANVKPMNH-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
  • Phenylacetaldehyde
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Alpha-hydrogen aldehyde
  • Ether
  • Aldehyde
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
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 Solubility2.9 g/LALOGPS
logP1.52ALOGPS
logP0.99ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.88 m³·mol⁻¹ChemAxon
Polarizability16.81 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]+137.07831661259
DarkChem[M-H]-133.3131661259
DeepCCS[M+H]+135.75930932474
DeepCCS[M-H]-131.99730932474
DeepCCS[M-2H]-169.77430932474
DeepCCS[M+Na]+145.31330932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.432859911
AllCCS[M+NH4]+139.932859911
AllCCS[M+Na]+141.132859911
AllCCS[M-H]-134.432859911
AllCCS[M+Na-2H]-135.532859911
AllCCS[M+HCOO]-136.832859911

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, 2022.3.33 minutes32390414
Predicted by Siyang on May 30, 202210.6353 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.94 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1403.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid329.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid134.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid193.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid92.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid501.2 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 Acid463.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)141.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid972.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid360.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1073.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid298.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid320.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate481.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA307.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water86.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HomovanillinCOC1=C(O)C=CC(CC=O)=C12581.9Standard polar33892256
HomovanillinCOC1=C(O)C=CC(CC=O)=C11407.8Standard non polar33892256
HomovanillinCOC1=C(O)C=CC(CC=O)=C11488.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Homovanillin,1TMS,isomer #1COC1=CC(CC=O)=CC=C1O[Si](C)(C)C1600.6Semi standard non polar33892256
Homovanillin,1TMS,isomer #2COC1=CC(C=CO[Si](C)(C)C)=CC=C1O1799.5Semi standard non polar33892256
Homovanillin,2TMS,isomer #1COC1=CC(C=CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C1849.5Semi standard non polar33892256
Homovanillin,2TMS,isomer #1COC1=CC(C=CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C1820.5Standard non polar33892256
Homovanillin,2TMS,isomer #1COC1=CC(C=CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C2031.2Standard polar33892256
Homovanillin,1TBDMS,isomer #1COC1=CC(CC=O)=CC=C1O[Si](C)(C)C(C)(C)C1855.5Semi standard non polar33892256
Homovanillin,1TBDMS,isomer #2COC1=CC(C=CO[Si](C)(C)C(C)(C)C)=CC=C1O2047.3Semi standard non polar33892256
Homovanillin,2TBDMS,isomer #1COC1=CC(C=CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2359.0Semi standard non polar33892256
Homovanillin,2TBDMS,isomer #1COC1=CC(C=CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2268.7Standard non polar33892256
Homovanillin,2TBDMS,isomer #1COC1=CC(C=CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2269.1Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023632
KNApSAcK IDNot Available
Chemspider ID133331
KEGG Compound IDC05581
BioCyc IDNot Available
BiGG ID46064
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151276
PDB IDNot Available
ChEBI ID28111
Food Biomarker OntologyNot Available
VMH ID3MOX4HPAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHarries, C. Homovanillin. Berichte der Deutschen Chemischen Gesellschaft (1915), 48 868-9. CODEN: BDCGAS ISSN:0365-9496. CAN 9:13972 AN 1915:13972
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mardh G, Vallee BL: Human class I alcohol dehydrogenases catalyze the interconversion of alcohols and aldehydes in the metabolism of dopamine. Biochemistry. 1986 Nov 18;25(23):7279-82. [PubMed:2432930 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
Enzyme Details
3. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
Enzyme Details
5. Aldehyde dehydrogenase family 3 member B2
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase family 3 member B1
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails