Bovine Metabolome Database: Showing metabocard for 5-Hydroxyindoleacetic acid (BMDB0000763)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:36:12 UTC

Update Date

2020-05-21 16:28:51 UTC

BMDB ID

BMDB0000763

Secondary Accession Numbers

BMDB00763

Metabolite Identification

Common Name

5-Hydroxyindoleacetic acid

Description

5-5-5-hydroxyindoleacetic acid, also known as 5-5-hydroxyindoleacetic acid or 5-hydroxy-1H-indole-3-acetate, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-5-5-hydroxyindoleacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 5-5-5-hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. 5-5-5-hydroxyindoleacetic acid participates in a number of enzymatic reactions, within cattle. In particular, 5-5-5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 5-5-5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. In cattle, 5-5-hydroxyindoleacetic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-HIAA	ChEBI
5-Hydroxy-1H-indole-3-acetic acid	ChEBI
5-Hydroxyindol-3-ylacetic acid	ChEBI
5-Hydroxyindole-3-acetic acid	ChEBI
5-Hydroxy-1H-indole-3-acetate	Generator
5-Hydroxyindol-3-ylacetate	Generator
5-Hydroxyindole-3-acetate	Generator
5-Hydroxyindoleacetate	Generator
5-Hydroxy-3-indolylacetate	HMDB
5-Hydroxy-iaa	HMDB
5-Hydroxy-indole-3-acetate	HMDB
5-Hydroxy-indole-3-acetic acid	HMDB
5-Hydroxyheteroauxin	HMDB
5-Hydroxyindole acetate	HMDB
5-Oxyindoleacetate	HMDB
5-Oxyindoleacetic acid	HMDB
5HIAA	HMDB
Hydroxyindoleacetate	HMDB
5-Hydroxyindolamine acetic acid	MeSH, HMDB
Hydroxyindoleacetic acid	MeSH, HMDB
5 Hydroxy 3 indoleacetic acid	MeSH, HMDB
5 Hydroxyindolamine acetic acid	MeSH, HMDB
5-Hydroxy-3-indoleacetic acid	MeSH, HMDB
Acetic acid, 5-hydroxyindolamine	MeSH, HMDB
Acid, hydroxyindoleacetic	MeSH, HMDB
Acid, 5-hydroxy-3-indoleacetic	MeSH, HMDB
Acid, 5-hydroxyindolamine acetic	MeSH, HMDB

Chemical Formula

C₁₀H₉NO₃

Average Molecular Weight

191.1834

Monoisotopic Molecular Weight

191.058243159

IUPAC Name

2-(5-hydroxy-1H-indol-3-yl)acetic acid

Traditional Name

hydroxyindoleacetic acid

CAS Registry Number

54-16-0

SMILES

OC(=O)CC1=CNC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)

InChI Key

DUUGKQCEGZLZNO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole-3-acetic acids (CHEBI:27823 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	161 - 163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	24 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.28	ALOGPS
logP	1.41	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.43 m³·mol⁻¹	ChemAxon
Polarizability	18.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0006-0390100000-f473f1a32542afd5d101	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1490100000-a72832b1524478059ef7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-0191000000-660345027702653fc000	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0293000000-66850e233e11ec787808	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0191200000-99e904e0c2698a9ec34d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0390100000-f473f1a32542afd5d101	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1490100000-a72832b1524478059ef7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0191000000-660345027702653fc000	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0390100000-77c9d80e625d0da33fcf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0691000000-ad9e4829206c93db526a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-0900000000-4aceed1a9f20cfdd5d35	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0229-5093000000-805b9af9a37ffd246f4c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-931e6e7603f58232f0e0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-0900000000-ec9ed3a4a7ed491064e7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-8900000000-b4144894cf8f60daf9fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e3daf51d70668c08950d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-052b-0900000000-88af3a616d054b8917e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-0900000000-cefb365d8f0aad3d766d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-0900000000-12e9d882014f1a7bfd4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-0900000000-7890fc93271437e3d2d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-1900000000-6c0974626895f2a0c437	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-003r-1900000000-9aa2c699af3e125036f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-3900000000-42fd55964480ac872c0e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000x-6900000000-61fc171a48c42517d25f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9400000000-0fd99ccea1ed33b42bfa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-5f8ae429e297482d98b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0900000000-759a3410e0268ce0d589	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-0900000000-0f6f5a0c9905b0c5883d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-4bf1424d8b0a831cae16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006w-0900000000-3e62c4d79b28ba65eab6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007p-2900000000-d626b2b22dd1b2bc9517	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-5f8ae429e297482d98b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0900000000-759a3410e0268ce0d589	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-0900000000-0f6f5a0c9905b0c5883d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-4bf1424d8b0a831cae16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006w-0900000000-3e62c4d79b28ba65eab6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007p-2900000000-d626b2b22dd1b2bc9517	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Brain
Liver
Neuron
Platelet
Prostate Tissue
Spleen
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tryptophan Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000763

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

5-HYDROXYINDOLE_ACETATE

BiGG ID

46167

Wikipedia Link

5-Hydroxyindoleacetic_acid

METLIN ID

2975

PubChem Compound

1826

PDB ID

Not Available

ChEBI ID

27823

References

Synthesis Reference

Asero, B.; Colo, V. A.; Vercellone, A. Preparation of 5-hydroxy-3-indoleacetic acid. Farmaco, Edizione Scientifica (1956), 11 219-20.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetylserotonin O-methyltransferase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine).
Gene Name:: ASMT
Uniprot ID:: P10950
Molecular weight:: 37924.0

Reactions

5-Hydroxyindoleacetic acid + S-Adenosylmethionine → 5-Methoxyindoleacetate + S-Adenosylhomocysteine	details

Enzyme Details

2. Aldehyde oxidase 1

General function:: Nucleotide transport and metabolism
Specific function:: Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:: AOX1
Uniprot ID:: P48034
Molecular weight:: 147611.0

Reactions

5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxide	details

Enzyme Details

3. Aldehyde dehydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P20000
Molecular weight:: 56653.0

Reactions

5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + NADH	details

Showing metabocard for 5-Hydroxyindoleacetic acid (BMDB0000763)

Structure for BMDB0000763 (5-Hydroxyindoleacetic acid)

Enzymes

Reactions

Reactions

Reactions