Showing Compound Card for 3,4-Dihydroxyphenylacetaldehyde (CDB005279)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (9) Show 13 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:27:16 UTC
Updated at2020-11-18 16:39:39 UTC
CannabisDB IDCDB005279
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,4-Dihydroxyphenylacetaldehyde
Description3,4-Dihydroxyphenylacetaldehyde, also known as protocatechuatealdehyde or 2-(3,4-dihydroxyphenyl)ethanal, 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. 3,4-Dihydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxyphenylacetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxyphenylacetaldehyde participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylacetaldehyde can be biosynthesized from dopamine through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-dihydroxyphenylacetaldehyde can be converted into 3,4-dihydroxybenzeneacetic acid through the action of the enzyme 3,4-dihydroxyphenylacetaldehyde. In humans, 3,4-dihydroxyphenylacetaldehyde is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as pot marjorams, muscadine grapes, rambutans, summer savories, and cottonseeds. This could make 3,4-dihydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups. 3,4-Dihydroxyphenylacetaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)ethanalChEBI
DOPALChEBI
ProtocatechuatealdehydeChEBI
DHPAA aldehydeMeSH
3,4-Dihydroxy-benzeneacetaldehydeHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.15
Monoisotopic Molecular Weight152.0473
IUPAC Name2-(3,4-dihydroxyphenyl)acetaldehyde
Traditional Namedopal
CAS Registry Number5707-55-1
SMILES
OC1=C(O)C=C(CC=O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
InChI KeyIADQVXRMSNIUEL-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
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
logP1.005Not Available
Predicted Properties
PropertyValueSource
logP1.15ALOGPS
logP0.85ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.4 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3900000000-7f82d1d31cd24be9e865Spectrum
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-8390000000-bba6c4376314951fb5eeSpectrum
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-19827d81a06a62c2b70a2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-2900000000-479d55c57638faa6d9cd2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9400000000-cadc5e95515b4cecf1f72015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b0ef024b4e5895ddea082015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-352f5ee2c302c824867e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-96da2068f1ed3e30ae472015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0900000000-588f3b3d236131a4fa7a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3900000000-d3765e83b72ff4e9c9332021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9100000000-63064bac00f3091d89c32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b75a7231958cf1fc53ec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-ed865ca228b5007b7ed42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-7cc4c0962b7233330b8c2021-09-22View 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
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 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
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Membrane primary amine oxidaseAOC317q21Q16853 details
Retina-specific copper amine oxidaseAOC217q21O75106 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003791
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023227
KNApSAcK IDC00052036
Chemspider ID106504
KEGG Compound IDC04043
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,4-Dihydroxyphenylacetaldehyde
METLIN IDNot Available
PubChem Compound119219
PDB IDNot Available
ChEBI ID27978
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 13 proteins in total.

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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. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
6. 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
7. 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
8. 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
9. 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

Only showing the first 10 proteins. There are 13 proteins in total.

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