Showing Compound 5-Hydroxyindole-3-acetic acid (FDB001403)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:57 UTC

Update date

2019-11-26 02:56:26 UTC

Primary ID

FDB001403

Secondary Accession Numbers

FDB030574

Chemical Information

FooDB Name

5-Hydroxyindole-3-acetic acid

Description

5-Hydroxyindoleacetic acid, also known as 5-HIAA 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-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. 5-Hydroxyindoleacetic acid has been detected, but not quantified in, several different foods, such as black mulberries (Morus nigra), anises (Pimpinella anisum), orange bell peppers (Capsicum annuum), mulberries (Morus), and bilberries (Vaccinium myrtillus). This could make 5-hydroxyindoleacetic acid a potential biomarker for the consumption of these foods. 5-Hydroxyindoleacetic acid, with regard to humans, has been found to be associated with several diseases such as hereditary spastic paraplegia, crohn's disease, metabolic syndrome, and perillyl alcohol administration for cancer treatment; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder carbamoyl phosphate synthetase deficiency. Based on a literature review a significant number of articles have been published on 5-Hydroxyindoleacetic acid.

CAS Number

54-16-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(5-hydroxy-1H-indol-3-yl)acetic acid	biospider
(5-hydroxyindol-3-yl)acetic acid	biospider
5 Hydroxy 3 indoleacetic acid	MeSH, HMDB
5 Hydroxyindolamine acetic acid	MeSH, HMDB
5-HIAA	ChEBI
5-Hydroxy-1H-indole-3-acetate	Generator
5-Hydroxy-1H-indole-3-acetic acid	ChEBI
5-Hydroxy-3-indoleacetic acid	MeSH, HMDB
5-Hydroxy-3-indolylacetate	HMDB
5-Hydroxy-iaa	HMDB

Showing 1 to 10 of 33 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.8 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H9NO3

IUPAC name

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

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

Isomeric SMILES

OC(=O)CC1=CNC2=CC=C(O)C=C12

Average Molecular Weight

191.1834

Monoisotopic Molecular Weight

191.058243159

Classification

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

Ingestion

Source:

Biological:

Animal

Plant:

Microbe:

Human gut microbiota

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

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	161-163 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-0390100000-f473f1a32542afd5d101	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, 3 TMS, GC-MS Spectrum	splash10-0006-1490100000-a72832b1524478059ef7	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-014i-0191000000-660345027702653fc000	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0293000000-66850e233e11ec787808	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-0191200000-99e904e0c2698a9ec34d	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-0390100000-f473f1a32542afd5d101	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-1490100000-a72832b1524478059ef7	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0191000000-660345027702653fc000	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-0390100000-77c9d80e625d0da33fcf	Spectrum
GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0691000000-ad9e4829206c93db526a	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0005-0900000000-4aceed1a9f20cfdd5d35	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0229-5093000000-805b9af9a37ffd246f4c	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Hydroxyindole-3-acetic acid, TBDMS_2_3, 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)	splash10-0002-0900000000-931e6e7603f58232f0e0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-0900000000-ec9ed3a4a7ed491064e7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-8900000000-b4144894cf8f60daf9fa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e3daf51d70668c08950d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-052b-0900000000-88af3a616d054b8917e4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-0900000000-cefb365d8f0aad3d766d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-0900000000-12e9d882014f1a7bfd4d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-0900000000-7890fc93271437e3d2d7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-1900000000-6c0974626895f2a0c437	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-003r-1900000000-9aa2c699af3e125036f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-3900000000-42fd55964480ac872c0e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000x-6900000000-61fc171a48c42517d25f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9400000000-0fd99ccea1ed33b42bfa	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-5f8ae429e297482d98b9	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0900000000-759a3410e0268ce0d589	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-0900000000-0f6f5a0c9905b0c5883d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-4bf1424d8b0a831cae16	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006w-0900000000-3e62c4d79b28ba65eab6	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007p-2900000000-d626b2b22dd1b2bc9517	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-5f8ae429e297482d98b9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0900000000-759a3410e0268ce0d589	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-0900000000-0f6f5a0c9905b0c5883d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-4bf1424d8b0a831cae16	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006w-0900000000-3e62c4d79b28ba65eab6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007p-2900000000-d626b2b22dd1b2bc9517	2015-05-27	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum