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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-31 13:02:28 UTC
Update Date2020-02-26 21:25:45 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?1582752345
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

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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
logP10(1.52) g/LALOGPS
logP10(0.99) g/LChemAxon
logS10(-1.8) g/LALOGPS
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

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

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Homovanillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-e28b59106188528267be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homovanillin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6970000000-a597b09f1ff1acebbc8a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homovanillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homovanillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 10V, Positive-QTOFsplash10-014i-0900000000-d1e8f15334f430895ace2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 20V, Positive-QTOFsplash10-014s-1900000000-e7c5332202c6a2921d0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 40V, Positive-QTOFsplash10-0a4j-9500000000-8692ad76fd38a1c456dc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 10V, Negative-QTOFsplash10-014i-0900000000-5560a290417d5b338a9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 20V, Negative-QTOFsplash10-014i-0900000000-ecdd9295a0eb88d0d20c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 40V, Negative-QTOFsplash10-0006-9600000000-3121b7d402f23864e3a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 10V, Positive-QTOFsplash10-052r-0900000000-a06af236d75a4fe9514a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 20V, Positive-QTOFsplash10-0a4r-1900000000-824acd5fd49e69091de82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 40V, Positive-QTOFsplash10-0a4r-9600000000-55f5cc9088e21fdfd1922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 10V, Negative-QTOFsplash10-01bi-0900000000-15f57513fdfffda8fc452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 20V, Negative-QTOFsplash10-00di-0900000000-abbd129d0f4894a88d6a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homovanillin 40V, Negative-QTOFsplash10-014l-9100000000-f583c2db9bbeb78e47be2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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

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
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
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
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
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
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