MiMeDB: Showing metabocard for 5-Hydroxyindoleacetic acid (MMDBc0000540)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:06 UTC

Update Date

2024-04-30 19:32:55 UTC

Metabolite ID

MMDBc0000540

Metabolite Identification

Common Name

5-Hydroxyindoleacetic acid

Description

5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, 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. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreich's ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886 ). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652302032018292D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.618010000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000540

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C10H9NO3

> <MOLECULAR_WEIGHT>
191.1834

> <EXACT_MASS>
191.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.70645401922691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.4061907766666666

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.558275552338404

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.215990424188327

> <JCHEM_PKA_STRONGEST_BASIC>
-5.50801830576937

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
50.433

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyindoleacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8667.8208666.935   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8661.2888661.519   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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

Molecular Formula

C₁₀H₉NO₃

Average Mass

191.1834

Monoisotopic Mass

191.058243159

IUPAC Name

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

Traditional Name

hydroxyindoleacetic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Feces
Liver
Neuron
Platelet
Prostate
Spleen
Testis
Urine

Tissue Locations

Brain
Liver
Neuron
Platelet
Prostate
Spleen
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191774	Acetylserotonin O-methyltransferase	Unknown	P46597	Homo sapiens
MMDBp0191797	Aldehyde oxidase	Unknown	Q06278	Homo sapiens
MMDBp0191961	4-trimethylaminobutyraldehyde dehydrogenase	Unknown	P49189	Homo sapiens
MMDBp0191963	Alpha-aminoadipic semialdehyde dehydrogenase	Unknown	P49419	Homo sapiens
MMDBp0191964	Aldehyde dehydrogenase family 1 member A3	Unknown	P47895	Homo sapiens
MMDBp0191965	Aldehyde dehydrogenase, mitochondrial	Unknown	P05091	Homo sapiens
MMDBp0191966	Fatty aldehyde dehydrogenase	Unknown	P51648	Homo sapiens
MMDBp0191967	Aldehyde dehydrogenase X, mitochondrial	Unknown	P30837	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aromatic l-amino acid decarboxylase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	9686366
Aromatic l-amino acid decarboxylase deficiency	Decreased	Association	Human Urine	HMDB	9686366
Aromatic l-amino acid decarboxylase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	16288991
Aromatic l-amino acid decarboxylase deficiency		Association	Human Urine	HMDB	16288991
Bipolar disorder	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	19756368
Carbamoyl phosphate synthetase deficiency	Increased	Association	Human Urine	HMDB	7680187
Celiac disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	6182605
Celiac disease	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	6182788
Epilepsy	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	803305
Friedreich's ataxia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Hereditary spastic paraplegia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Major depressive disorder	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	9004051
Olivopontocerebral atrophy	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Schizophrenia	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	7595563
Schizophrenia		Association	Human Blood	HMDB	2480613
Schizophrenia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	6184954
Sepiapterin reductase deficiency	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	18502672
Eosinophilic esophagitis	Decreased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Increased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.027				uM	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	0.2				umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	2.2				umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0025		0.0000	0.0050	uM	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	HMDB	16288991
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0120	0.0220	uM	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	0.9	0.0			umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	HMDB	16288991
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0912	0.0387			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0983	0.0444			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.104	0.0386			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.112	0.0483			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.116	0.0479			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.116	0.053			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.123	0.0505			uM	Not Specified	Not Specified	Bipolar disorder	HMDB	19756368
Human Urine	Detected and Quantified			0.8	1.4	umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	HMDB	8503438
Human Urine	Detected and Quantified	5				umol/mmol creatinine	Adult (>18 years old)	Male	Carcinoid tumors	HMDB	7680187
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0703	0.0254			uM	Adult (>18 years old)	Both	celiac disease	HMDB	6182605
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.071	0.0268			uM	Adult (>18 years old)	Not Specified	celiac disease	HMDB	6182788
Human Urine	Detected and Quantified	0.0921				umol/mmol creatinine	Adolescent (13-18 years old)	Female	Dopamine-serotonin Vesicular Transport Defect	HMDB	23363473
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.33	0.04			uM	Children (1-13 years old)	Both	Epilepsy	HMDB	803305
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.1	0.01			uM	Adult (>18 years old)	Both	Friedreich's ataxia	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.1	0.02			uM	Adult (>18 years old)	Both	Autosomal recessive spastic ataxia of Charlevoix-Saguena	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.08	0.08			uM	Adult (>18 years old)	Both	Major depression	HMDB	9004051
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.11	0.01			uM	Adult (>18 years old)	Both	Olivopontocerebellar atrophy (OPCA)	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.117				uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.122				uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.151				uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.519				uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.22725		0.117	0.519	uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.019	0.0094			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	7595563
Human Blood	Detected and Quantified	0.0449	0.0140			uM	Adult (>18 years old)	Female	Schizophrenia	HMDB	2480613
Human Blood	Detected and Quantified	0.0475	0.0130			uM	Adult (>18 years old)	Male	Schizophrenia	HMDB	2480613
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.056	0.022			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	6184954
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0045		0.004	0.005	uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	HMDB	18502672
Human Urine	Detected and Quantified	1.18				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified			0	0.0314	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	23363473
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.025	0.011			uM	Adult (>18 years old)	Both	Normal	HMDB	7595563
Human Blood	Detected and Quantified	0.0516	0.0068			uM	Adult (>18 years old)	Both	Normal	HMDB	2480613
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.07	0.14	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	6182605
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.080	0.023			uM	Adult (>18 years old)	Both	Normal	HMDB	6184954
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.1	0.245	uM	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.109	0.214	uM	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.119	0.608	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.120	0.400	uM	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Urine	Detected and Quantified			0.3	5.1	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	8503438
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.307		0.152	0.462	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	16288991
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.4	0.07			uM	Adult (>18 years old)	Male	Normal	HMDB	8884658
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.428	1.122	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	18294893
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.47		0.15	0.80	uM	Infant (0-1 year old)	Both	Normal	HMDB	11486900
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.61	0.06			uM	Children (1-13 years old)	Both	Normal	HMDB	803305
Human Urine	Detected and Quantified	1.1	0.5			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Urine	Detected and Quantified			1.4	1.7	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.5		0	7.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified			1.5	2.0	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	11.0		4.0	18.0	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	16288991
Human Urine	Detected and Quantified	2.4	0.40			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7680187
Human Urine	Detected and Quantified	2.9		0.4	5.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			3.900	17.700	umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Urine	Detected and Quantified	4.75	5.38			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	5.004	1.463			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	69.452	34.984			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	54.058	23.536			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.583	5.31			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<21.85				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.143	0.045			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.143	0.0450			uM	Not Specified	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.57	0.38			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	3.0		0.48	4.5	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24390407
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mann JJ, McBride PA, Brown RP, Linnoila M, Leon AC, DeMeo M, Mieczkowski T, Myers JE, Stanley M: Relationship between central and peripheral serotonin indexes in depressed and suicidal psychiatric inpatients. Arch Gen Psychiatry. 1992 Jun;49(6):442-6. doi: 10.1001/archpsyc.1992.01820060022003. [PubMed:1376106 ]
Celada P, Sarrias MJ, Artigas F: Serotonin and 5-hydroxyindoleacetic acid in plasma. Potential use as peripheral measures of MAO-A activity. J Neural Transm Suppl. 1990;32:149-54. doi: 10.1007/978-3-7091-9113-2_21. [PubMed:1708403 ]
Borg S, Kvande H, Liljeberg P, Mossberg D, Valverius P: 5-Hydroxyindoleacetic acid in cerebrospinal fluid in alcoholic patients under different clinical conditions. Alcohol. 1985 May-Jun;2(3):415-8. doi: 10.1016/0741-8329(85)90106-5. [PubMed:2411275 ]
Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. [PubMed:2421946 ]
Korpi ER, Kleinman JE, Goodman SI, Phillips I, DeLisi LE, Linnoila M, Wyatt RJ: Serotonin and 5-hydroxyindoleacetic acid in brains of suicide victims. Comparison in chronic schizophrenic patients with suicide as cause of death. Arch Gen Psychiatry. 1986 Jun;43(6):594-600. doi: 10.1001/archpsyc.1986.01800060088011. [PubMed:2423050 ]
Fukuda H, Nakamura S, Hara K, Udaka F, Kameyama M: [Study on the concentration of 5-hydroxyindoleacetic acid (5-HIAA) in the lumbar cerebrospinal fluid (CSF) in neurological diseases]. Rinsho Shinkeigaku. 1989 Sep;29(9):1192-4. [PubMed:2480863 ]
Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. [PubMed:2692637 ]
Owens MJ, Nemeroff CB: Role of serotonin in the pathophysiology of depression: focus on the serotonin transporter. Clin Chem. 1994 Feb;40(2):288-95. [PubMed:7508830 ]
Lambert GW, Kaye DM, Cox HS, Vaz M, Turner AG, Jennings GL, Esler MD: Regional 5-hydroxyindoleacetic acid production in humans. Life Sci. 1995;57(3):255-67. doi: 10.1016/0024-3205(95)00269-c. [PubMed:7541101 ]
Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. doi: 10.3109/10401239309148828. [PubMed:8312985 ]
Rotondo A, Schuebel K, Bergen A, Aragon R, Virkkunen M, Linnoila M, Goldman D, Nielsen D: Identification of four variants in the tryptophan hydroxylase promoter and association to behavior. Mol Psychiatry. 1999 Jul;4(4):360-8. doi: 10.1038/sj.mp.4000578. [PubMed:10483053 ]
Castejon AM, Paez X, Hernandez L, Cubeddu LX: Use of intravenous microdialysis to monitor changes in serotonin release and metabolism induced by cisplatin in cancer patients: comparative effects of granisetron and ondansetron. J Pharmacol Exp Ther. 1999 Dec;291(3):960-6. [PubMed:10565811 ]
Walendzik H, Zimmer G, Skopp G: [Serotonin, 5-hydroxyindolylacetic acid and cholesterol content in blood, cerebrospinal fluid and brain areas for differentiation of suicidal from non-suicidal cause of death]. Arch Kriminol. 2000 May-Jun;205(5-6):131-44. [PubMed:10923167 ]
Ilkhanizadeh B, Owji AA, Tavangar SM, Vasei M, Tabei SM: Spot urine 5-hydroxy indole acetic acid and acute appendicitis. Hepatogastroenterology. 2001 May-Jun;48(39):609-13. [PubMed:11462886 ]
Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. doi: 10.1007/pl00022917. [PubMed:11697689 ]
Carpenter LL, Anderson GM, Siniscalchi JM, Chappell PB, Price LH: Acute changes in cerebrospinal fluid 5-HIAA following oral paroxetine challenge in healthy humans. Neuropsychopharmacology. 2003 Feb;28(2):339-47. doi: 10.1038/sj.npp.1300025. [PubMed:12589387 ]
Li JM, Kong LD, Wang YM, Cheng CH, Zhang WY, Tan WZ: Behavioral and biochemical studies on chronic mild stress models in rats treated with a Chinese traditional prescription Banxia-houpu decoction. Life Sci. 2003 Nov 21;74(1):55-73. doi: 10.1016/j.lfs.2003.06.030. [PubMed:14575813 ]
Christofides J, Bridel M, Egerton M, Mackay GM, Forrest CM, Stoy N, Darlington LG, Stone TW: Blood 5-hydroxytryptamine, 5-hydroxyindoleacetic acid and melatonin levels in patients with either Huntington's disease or chronic brain injury. J Neurochem. 2006 May;97(4):1078-88. doi: 10.1111/j.1471-4159.2006.03807.x. Epub 2006 Mar 29. [PubMed:16573644 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Showing metabocard for 5-Hydroxyindoleacetic acid (MMDBc0000540)

MOL for #<Metabolite:0x00007f9251de3470>

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Structure for #<Metabolite:0x00007f9251de3470>

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