Showing Compound Card for 4-Hydroxyphenylacetaldehyde (CDB005152)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (8) Show 10 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:14:34 UTC
Updated at2020-11-18 16:39:26 UTC
CannabisDB IDCDB005152
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Hydroxyphenylacetaldehyde
Description4-Hydroxyphenylacetaldehyde, also known as POH-PH-CH2CHO, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 4-Hydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as purple mangosteens, cottonseeds, garden cress, borages, and colorado pinyons. This could make 4-hydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. These natural products include berberine and morphine. 4-Hydroxyphenylacetaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(4-Hydroxyphenyl)acetaldehydeChEBI
p-HydroxyphenylacetaldehydeChEBI
POH-PH-CH2CHOChEBI
(4-Hydroxyphenyl)acetaldehydeHMDB
(p-Hydroxyphenyl)acetaldehydeHMDB
4-HydroxybenzeneacetaldehydeHMDB
4-HydroxyphenylacetadehydeHMDB
4-HydroxyphenylacetaldehydeHMDB
Chemical FormulaC8H8O2
Average Molecular Weight136.15
Monoisotopic Molecular Weight136.0524
IUPAC Name2-(4-hydroxyphenyl)acetaldehyde
Traditional Namep-hydroxyphenylacetaldehyde
CAS Registry Number7339-87-9
SMILES
OC1=CC=C(CC=O)C=C1
InChI Identifier
InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2
InChI KeyIPRPPFIAVHPVJH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.379Not Available
Predicted Properties
PropertyValueSource
logP1.59ALOGPS
logP1.15ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.42 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Hydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-5900000000-dee6bd2327885b9b9c35Spectrum
Predicted GC-MS4-Hydroxyphenylacetaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-5900000000-052b7c5a508b36e0512fSpectrum
Predicted GC-MS4-Hydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c592acce12d2ba1340402015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2900000000-90058ffcbfd58f5dff5b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9500000000-a8abea2510950f3372952015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3f4ed034f10b0d6a25b42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-99115e80b538ba6b23062015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6c9913d203a267c921862015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-4900000000-e2bf91e8ab2ae47d90962021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9600000000-ff10a0510f947f4766882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-b447fa4b15009b677f8f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-59dcda3398a30862c88d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-7a7b9a9d95399c23529b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-b2c6c4e6f393a74588222021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Amine oxidase [flavin-containing] BMAOBXp11.23P27338 details
Amine oxidase [flavin-containing] AMAOAXp11.3P21397 details
Aldehyde dehydrogenase, dimeric NADP-preferringALDH3A117p11.2P30838 details
Aldehyde dehydrogenase family 1 member A3ALDH1A315q26.3P47895 details
Membrane primary amine oxidaseAOC317q21Q16853 details
Retina-specific copper amine oxidaseAOC217q21O75106 details
Aldehyde dehydrogenase family 3 member B2ALDH3B211q13P48448 details
Aldehyde dehydrogenase family 3 member B1ALDH3B111q13P43353 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Membrane primary amine oxidaseAOC317q21Q16853 details
Retina-specific copper amine oxidaseAOC217q21O75106 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003767
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023224
KNApSAcK IDC00051850
Chemspider ID389113
KEGG Compound IDC03765
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylacetaldehyde
METLIN IDNot Available
PubChem Compound440113
PDB IDNot Available
ChEBI ID15621
References
General ReferencesNot Available

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
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
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
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
Enzyme Details
5. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Enzyme Details
6. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Enzyme Details
7. 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
Enzyme Details
8. 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