Cannabis Compound Database: Showing Compound Card for Acetaldehyde (CDB000045)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (21) Show 30 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:22:45 UTC

Updated at

2020-12-07 19:06:59 UTC

CannabisDB ID

CDB000045

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Acetaldehyde

Description

Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are aldehydes with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol; which is mediated by the enzyme alcohol dehydrogenase 1B. In addition, acetaldehyde can be converted into acetic acid; which is mediated by mitochondrial aldehyde dehydrogenases. Industrially, the main method of production of acetaldehyde is via the oxidation of ethylene via the Wacker process. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process for producing acetaldehyde exceeded 2 million tonnes annually. Acetaldehyde is found in a number of different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine), Acetaldehyde has also been detected, but not quantified in, several different foods, such as malabar plums, malus (crabapple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. As a food constituent, acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and Crohn's disease. Acetaldehyde has also been linked to several inborn metabolic disorders including aldehyde dehydrogenase deficiency (III). The level at which an average consumer can detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Plastics Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. Acetaldehyde is known to be the most abundant carcinogen in tobacco smoke; it is easily dissolved in saliva while smoking (PMID:17382522 , PMID:21556207 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acetaldehyd	ChEBI
Acetaldehydes	ChEBI
Acetic aldehyde	ChEBI
Azetaldehyd	ChEBI
Ethanal	ChEBI
Ethyl aldehyde	ChEBI
Aldehyde	HMDB

Chemical Formula

C₂H₄O

Average Molecular Weight

44.05

Monoisotopic Molecular Weight

44.0262

IUPAC Name

acetaldehyde

Traditional Name

acetaldehyde

CAS Registry Number

75-07-0

SMILES

CC=O

InChI Identifier

InChI=1S/C2H4O/c1-2-3/h2H,1H3

InChI Key

IKHGUXGNUITLKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Short-chain aldehydes

Alternative Parents

Substituents

Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aldehyde (CHEBI:15343 )
an <i>n</i>-alkanal (ACETALD )

Ontology

Physiological effect

Health effect:

Health condition:

Cancer

Metabolism and nutrition disorders:

Aldehyde dehydrogenase deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Environmental:

Biological:

Animal

Microbe:

Helicobacter:

Helicobacter pylori

Plant:

Biological location:

Role

Indirect biological role:

Industrial application:

Food and nutrition

Environmental role:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-123 °C	Not Available
Boiling Point	20.2 °C	Wikipedia
Water Solubility	1000 mg/mL	Not Available
logP	-0.34	TSCATS

Predicted Properties

Property	Value	Source
logP	-0.01	ALOGPS
logP	-0.38	ChemAxon
logS	0.71	ALOGPS
pKa (Strongest Acidic)	16.73	ChemAxon
pKa (Strongest Basic)	-6.9	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	0	ChemAxon
Refractivity	11.72 m³·mol⁻¹	ChemAxon
Polarizability	4.48 Å³	ChemAxon
Number of Rings	0	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)	splash10-002f-9000000000-65d53ef91644a0bacd6c	2014-09-20	View Spectrum
Predicted GC-MS	Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-69e31ccd415894a68912	Spectrum
Predicted GC-MS	Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetaldehyde, 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)	splash10-0002-9000000000-f1274d4b6066776ca898	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001l-9000000000-c1e37abbf2ad6054dc10	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000t-9000000000-2289ead4f7210282cd87	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-cf54221d95714f5478c4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-8d8afe7422ae76f7ebb9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9000000000-d68dec9f846cfe9acc72	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-4430d6a790eca4132aa4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-607a755de038203a6b68	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-63c9f623d8dc4b1e60a2	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-0d922cdfd7f6947230c0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2758497e574a09010547	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyruvate Metabolism
Ethanol Degradation		Not Available
Disulfiram Action Pathway		Not Available
Pentose Phosphate Pathway
Glucose-6-phosphate dehydrogenase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aspartate aminotransferase, mitochondrial	GOT2	16q21	P00505	details
4-trimethylaminobutyraldehyde dehydrogenase	ALDH9A1	1q23.1	P49189	details
Aldehyde dehydrogenase, dimeric NADP-preferring	ALDH3A1	17p11.2	P30838	details
Alpha-aminoadipic semialdehyde dehydrogenase	ALDH7A1	5q31	P49419	details
Aldehyde dehydrogenase family 1 member A3	ALDH1A3	15q26.3	P47895	details
Aldehyde dehydrogenase, mitochondrial	ALDH2	12q24.2	P05091	details
Fatty aldehyde dehydrogenase	ALDH3A2	17p11.2	P51648	details
Aldehyde dehydrogenase X, mitochondrial	ALDH1B1	9p11.1	P30837	details
6-pyruvoyl tetrahydrobiopterin synthase	PTS	11q22.3	Q03393	details
Alcohol dehydrogenase [NADP(+)]	AKR1A1	1p33-p32	P14550	details
Alcohol dehydrogenase 4	ADH4	4q22	P08319	details
Aldehyde dehydrogenase family 3 member B2	ALDH3B2	11q13	P48448	details
Aldehyde dehydrogenase family 3 member B1	ALDH3B1	11q13	P43353	details
Alcohol dehydrogenase class-3	ADH5	4q23	P11766	details
Alcohol dehydrogenase 1B	ADH1B	4q23	P00325	details
Alcohol dehydrogenase class 4 mu/sigma chain	ADH7	4q23-q24	P40394	details
Alcohol dehydrogenase 1A	ADH1A	4q23	P07327	details
Alcohol dehydrogenase 6	ADH6	4q23	P28332	details
Alcohol dehydrogenase 1C	ADH1C	4q23	P00326	details
Putative deoxyribose-phosphate aldolase	DERA	12p12.3	Q9Y315	details
Ethanolamine-phosphate phospho-lyase	AGXT2L1	4q25	Q8TBG4	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
6-pyruvoyl tetrahydrobiopterin synthase	PTS	11q22.3	Q03393	details
Alcohol dehydrogenase 4	ADH4	4q22	P08319	details
Alcohol dehydrogenase class-3	ADH5	4q23	P11766	details
Alcohol dehydrogenase 1B	ADH1B	4q23	P00325	details
Alcohol dehydrogenase class 4 mu/sigma chain	ADH7	4q23-q24	P40394	details
Alcohol dehydrogenase 1A	ADH1A	4q23	P07327	details
Alcohol dehydrogenase 6	ADH6	4q23	P28332	details
Alcohol dehydrogenase 1C	ADH1C	4q23	P00326	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alcohol dehydrogenase class 4 mu/sigma chain	ADH7	4q23-q24	P40394	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000990

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15343

References

General References

Talhout R, Opperhuizen A, van Amsterdam JG: Role of acetaldehyde in tobacco smoke addiction. Eur Neuropsychopharmacol. 2007 Oct;17(10):627-36. doi: 10.1016/j.euroneuro.2007.02.013. Epub 2007 Mar 23. [PubMed:17382522 ]
Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. [PubMed:21556207 ]

Only showing the first 10 proteins. There are 30 proteins in total.

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Enzymes

Enzyme Details

1. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Enzyme Details

2. 4-trimethylaminobutyraldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:: ALDH9A1
Uniprot ID:: P49189
Molecular weight:: 56291.485

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. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:: ALDH7A1
Uniprot ID:: P49419
Molecular weight:: 58486.74

Enzyme Details

5. 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

6. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Enzyme Details

7. Fatty aldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:: ALDH3A2
Uniprot ID:: P51648
Molecular weight:: 54847.36

Enzyme Details

8. Aldehyde dehydrogenase X, mitochondrial

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.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Enzyme Details

9. 6-pyruvoyl tetrahydrobiopterin synthase

General function:: Involved in 6-pyruvoyltetrahydropterin synthase activity
Specific function:: Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:: PTS
Uniprot ID:: Q03393
Molecular weight:: 16385.63

Enzyme Details

10. Alcohol dehydrogenase [NADP(+)]

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
Gene Name:: AKR1A1
Uniprot ID:: P14550
Molecular weight:: 36572.71

Only showing the first 10 proteins. There are 30 proteins in total.

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Showing Compound Card for Acetaldehyde (CDB000045)

Structure for CDB000045 (Acetaldehyde)

Enzymes