Showing Compound 5-hydroxyindole acetaldehyde (FDB030573)

Record Information

Version

1.0

Creation date

2015-05-07 19:32:06 UTC

Update date

2019-11-26 03:21:49 UTC

Primary ID

FDB030573

Secondary Accession Numbers

FDB023299

Chemical Information

FooDB Name

5-hydroxyindole acetaldehyde

Description

5-hydroxyindoleacetaldehyde, also known as 5-hial, is a member of the class of compounds known as hydroxyindoles. Hydroxyindoles are organic compounds containing an indole moiety that carries a hydroxyl group. 5-hydroxyindoleacetaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxyindoleacetaldehyde can be found in a number of food items such as durian, squashberry, black huckleberry, and daikon radish, which makes 5-hydroxyindoleacetaldehyde a potential biomarker for the consumption of these food products. 5-hydroxyindoleacetaldehyde can be found primarily in blood, feces, and urine, as well as in human kidney and liver tissues. In humans, 5-hydroxyindoleacetaldehyde is involved in the tryptophan metabolism.

CAS Number

1892-21-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(5-Hydroxy-1H-indol-3-yl)acetaldehyde	HMDB
(5-Hydroxyindol-3-yl)acetaldehyde	HMDB
5-Hial	ChEBI
5-Hydroxy-1H-indole-3-acetaldehyde	HMDB
5-Hydroxyindole-3-acetaldehyde	ChEBI
5-Hydroxytryptaldehyde	HMDB
Hydroxyindoleacetaldehyde	HMDB

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.25	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.51 m³·mol⁻¹	ChemAxon
Polarizability	17.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H9NO2

IUPAC name

2-(5-hydroxy-1H-indol-3-yl)acetaldehyde

InChI Identifier

InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2

InChI Key

OBFAPCIUSYHFIE-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC2=C(NC=C2CC=O)C=C1

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

Classification

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Alpha-hydrogen aldehyde
Pyrrole
Heteroaromatic compound
Azacycle
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyindoles (CHEBI:50157 )
indoleacetaldehyde (CHEBI:50157 )
a small molecule (5-HYDROXYINDOLE_ACETALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	5-Hydroxyindoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-0900000000-82ea66debc45b5a54912	Spectrum
Predicted GC-MS	5-Hydroxyindoleacetaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-4590000000-148aa38d23d73f5990a5	Spectrum
Predicted GC-MS	5-Hydroxyindoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindoleacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-34afefea4e019e029852	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-057j-0900000000-c324c5351368276b781e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ng-2900000000-b5cae8ea903e8b80ef0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-f492ed9bb605e0b7b03b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-9fb25b933c4987b62dee	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2900000000-0c78360f8596defdda87	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-8c82c2093e14f3857e5c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0900000000-6c3085f4067426eeb1f3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-1900000000-fc0d25838e197398d090	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ce155c63a4e18d180895	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-0900000000-3967b0a653903263d918	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-b3f6f7944533b77bfd8b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Abalone	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Abiyuch	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acerola	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acorn	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Adzuki bean	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agar	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agave	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska blueberry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska wild rhubarb	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alfalfa	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis