Cannabis Compound Database: Showing Compound Card for Indoleacetaldehyde (CDB004890)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 11 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:47:25 UTC

Updated at

2020-11-18 16:38:56 UTC

CannabisDB ID

CDB004890

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Indoleacetaldehyde

Description

Indoleacetaldehyde, also known as tryptaldehyde, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. An indoleacetaldehyde that is acetaldehyde in which one of the methyl hydrogens are replaced by a indol-3-yl group. Indoleacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, indoleacetaldehyde participates in a number of enzymatic reactions. In particular, indoleacetaldehyde can be biosynthesized from tryptamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In addition, indoleacetaldehyde can be converted into indoleacetic acid through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, indoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, Indoleacetaldehyde has been detected, but not quantified in, several different foods, such as ohelo berries, mamey sapotes, turnips, chives, and pummelo. This could make indoleacetaldehyde a potential biomarker for the consumption of these foods. Indoleacetaldehyde 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
1H-Indole-3-acetaldehyde	ChEBI
2-(indol-3-yl)Acetaldehyde	ChEBI
Indole-3-acetaldehyde	ChEBI
1H-indol-3-Ylacetaldehyde	HMDB
2-(3-Indolyl)acetaldehyde	HMDB
indol-3-Ylacetaldehyde	HMDB
Tryptaldehyde	HMDB

Chemical Formula

C₁₀H₉NO

Average Molecular Weight

159.18

Monoisotopic Molecular Weight

159.0684

IUPAC Name

2-(1H-indol-3-yl)acetaldehyde

Traditional Name

indole-3-acetaldehyde

CAS Registry Number

2591-98-2

SMILES

O=CCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2

InChI Key

WHOOUMGHGSPMGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Alpha-hydrogen aldehyde
Pyrrole
Heteroaromatic compound
Azacycle
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoleacetaldehyde (CHEBI:18086 )
a small molecule (INDOLE_ACETALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Biofluid and excreta:

Subcellular:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.32	ALOGPS
logP	1.55	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.73	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.53 m³·mol⁻¹	ChemAxon
Polarizability	16.87 Å³	ChemAxon
Number of Rings	2	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
GC-MS	Indoleacetaldehyde, 1 TMS, GC-MS Spectrum	splash10-0udi-3790000000-d0624211b87a8c0c6eb0	Spectrum
GC-MS	Indoleacetaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0fb9-1890000000-f47966a3402f39ffb15a	Spectrum
GC-MS	Indoleacetaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0ufr-2890000000-4661feb288e5418df124	Spectrum
GC-MS	Indoleacetaldehyde, 2 TMS, GC-MS Spectrum	splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2	Spectrum
GC-MS	Indoleacetaldehyde, 2 TMS, GC-MS Spectrum	splash10-0udi-1669000000-87b7c126c24be968871e	Spectrum
GC-MS	Indoleacetaldehyde, 3 TMS, GC-MS Spectrum	splash10-0006-0910000000-f73cd81db2b9712b4661	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-1490000000-614e405de09537fc4b35	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9430000000-c2d7214f3eaf0a20e864	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9430000000-75194e386ef16f3f47b2	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-3790000000-d0624211b87a8c0c6eb0	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0fb9-1890000000-f47966a3402f39ffb15a	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0ufr-2890000000-4661feb288e5418df124	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-1669000000-87b7c126c24be968871e	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0006-0910000000-f73cd81db2b9712b4661	Spectrum
GC-MS	Indoleacetaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-1490000000-614e405de09537fc4b35	Spectrum
Predicted GC-MS	Indoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053r-0900000000-4528170aed93d1f2f6cf	Spectrum
Predicted GC-MS	Indoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a7i-0900000000-3a12e240a01798e6d515	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-0d6b7064551a83893c6e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0159-0900000000-868e767ca141d74ec888	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0059-0900000000-dea5f8a3cd655d34e727	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-0900000000-03eb4dd9323023a06970	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ec1cff588ddd81294ce1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-a292bcb2abf1d2004296	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03yl-0900000000-c9491489626575ac821c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-3900000000-c4a5850dd4b1a7da14e1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8354b2e6155a5677c353	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-2bd561638cdcf5535ba5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-3900000000-bb8a2da37c41a8f5040e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0api-0900000000-ab705375598dd738ce6d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-924d3410f1e3855c2336	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-74f0d61a0a5ca7d19925	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ec-0900000000-f09223778d8ebf23f2f5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-474bb30e410332db437a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fc0-3900000000-8e24fed06b1ae0ed20af	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tryptophan Metabolism

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
4-trimethylaminobutyraldehyde dehydrogenase	ALDH9A1	1q23.1	P49189	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
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	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

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

HMDB0001190

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

Not Available

METLIN ID

6068

PubChem Compound

800

PDB ID

Not Available

ChEBI ID

18086

References

General References

Not Available

Only showing the first 10 proteins. There are 11 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. 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

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. 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

Only showing the first 10 proteins. There are 11 proteins in total.

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Showing Compound Card for Indoleacetaldehyde (CDB004890)

Structure for CDB004890 (Indoleacetaldehyde)

Enzymes