Cannabis Compound Database: Showing Compound Card for Phenylacetaldehyde (CDB004975)

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Record Information

Version

1.0

Created at

2020-04-17 18:56:19 UTC

Updated at

2020-12-07 19:11:23 UTC

CannabisDB ID

CDB004975

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phenylacetaldehyde

Description

Phenylacetaldehyde, also known as alpha-tolualdehyde or 2-phenylethanal, 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. Phenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetaldehyde exists in all living species, ranging from bacteria to humans. Phenylacetaldehyde is a sweet, bitter, and clover tasting compound. Outside of the human body, Phenylacetaldehyde is found, on average, in the highest concentration within a few different foods, such as corns, beers, and white wines and in a lower concentration in safflowers, taco, and bilberries. Phenylacetaldehyde has also been detected, but not quantified in, several different foods, such as small-leaf lindens, green beans, sweet oranges, mountain yams, and common thymes. This could make phenylacetaldehyde a potential biomarker for the consumption of these foods. An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. Phenylacetaldehyde is a potentially toxic compound. Phenylacetaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-oxo-2-Phenylethane	ChEBI
2-Phenylacetaldehyde	ChEBI
2-Phenylethanal	ChEBI
alpha-Phenylacetaldehyde	ChEBI
alpha-Tolualdehyde	ChEBI
alpha-Toluic aldehyde	ChEBI
Benzacetaldehyde	ChEBI
Benzeneacetaldehyde	ChEBI
Hyacinthin	ChEBI
Phenacetaldehyde	ChEBI
Phenylacetic aldehyde	ChEBI
a-Phenylacetaldehyde	Generator
Α-phenylacetaldehyde	Generator
a-Tolualdehyde	Generator
Α-tolualdehyde	Generator
a-Toluic aldehyde	Generator
Α-toluic aldehyde	Generator
.alpha.-toluic aldehyde	HMDB
Benzenacetaldehyde	HMDB
Benzylcarboxaldehyde	HMDB
FEMA no. 2974	HMDB
Oxophenylethane	HMDB
Phenyl-acetaldehyde	HMDB
Phenylethanal	HMDB

Chemical Formula

C₈H₈O

Average Molecular Weight

120.15

Monoisotopic Molecular Weight

120.0575

IUPAC Name

2-phenylacetaldehyde

Traditional Name

phenylacetaldehyde

CAS Registry Number

122-78-1

SMILES

O=CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2

InChI Key

DTUQWGWMVIHBKE-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetaldehydes

Direct Parent

Phenylacetaldehydes

Alternative Parents

Substituents

Phenylacetaldehyde
Alpha-hydrogen aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-CH2-containing aldehyde (CHEBI:16424 )
phenylacetaldehydes (CHEBI:16424 )
an aryl aldehyde (PHENYLACETALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Environmental:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Feces

Role

Environmental role:

Water pollutant

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	120.5 - 121.5 °C	Not Available
Boiling Point	195 °C	Wikipedia
Water Solubility	2.21 g/L	Wikipedia
logP	1.78	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.75	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.44 m³·mol⁻¹	ChemAxon
Polarizability	12.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-e7ef9a5c5a6cc5674cd1	2014-09-20	View Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-9400000000-bec6e42b47ad1306960f	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-014l-9700000000-152bdd5b77d6af9657ec	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-d37cbef4100302e951de	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-9400000000-bec6e42b47ad1306960f	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-014l-9700000000-152bdd5b77d6af9657ec	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-9400000000-e75d2f0bf82f16a80388	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-9400000000-32573b7f6ab690a27e3e	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-5900000000-21e85148d15d190553c4	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-5900000000-4471e0916a32cf4df7ac	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-5900000000-650012e69d0a89a2fd4a	Spectrum
GC-MS	Phenylacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-5900000000-c80b65e383f833509e0f	Spectrum
Predicted GC-MS	Phenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-b3923f5fae42c664ac4a	Spectrum
Predicted GC-MS	Phenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-4900000000-5001b07cef2fed3caa2c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9100000000-048e2f1b42f7bd5104be	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fb9-9000000000-fc1fbd4e7c49f44ba764	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positive	splash10-0006-9000000000-bc0fa2967da6872f3a47	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0ufr-9700000000-507b63b585578b670628	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8c96fee71b311d751181	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-2900000000-4b405668c302f69a4bc7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9300000000-fe46a418a2f0124566c3	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-4e064e0123dc18b6136a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-02fff0bd874e6e8616bb	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9200000000-340c7a60a7708fa801f1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-9000000000-e37fda57674e1a53ea10	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-2071e5b3f45157a1da9c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9100000000-219bfc0a518871479977	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kf-9300000000-3fb47a0274f5792b4bd1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cc66f13f72898a397be6	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amine oxidase [flavin-containing] B	MAOB	Xp11.23	P27338	details
Amine oxidase [flavin-containing] A	MAOA	Xp11.3	P21397	details
Aldehyde dehydrogenase, dimeric NADP-preferring	ALDH3A1	17p11.2	P30838	details
Aldehyde dehydrogenase family 1 member A3	ALDH1A3	15q26.3	P47895	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Aldehyde dehydrogenase family 3 member B2	ALDH3B2	11q13	P48448	details
Aldehyde dehydrogenase family 3 member B1	ALDH3B1	11q13	P43353	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0006236

DrugBank ID

DB02178

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

998

PDB ID

Not Available

ChEBI ID

16424

References

General References

Not 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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Showing Compound Card for Phenylacetaldehyde (CDB004975)

Structure for CDB004975 (Phenylacetaldehyde)

Enzymes