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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-27 16:49:38 UTC
HMDB IDHMDB0000197
Secondary Accession Numbers
  • HMDB00197
Metabolite Identification
Common NameIndoleacetic acid
DescriptionIndoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Higher levels of IAA are associated with bacteria from Clostridium species including C. stricklandii, C. lituseburense, C. subterminale, and C. putrefaciens (PMID: 12173102 ). IAA can be found in Agrobacterium, Azospirillum, Bacillus, Bradyrhizobium, Clostridium, Enterobacter, Pantoea, Pseudomonas, Rhizobium (PMID: 12173102 , PMID: 17555270 , PMID: 12147474 , PMID: 19400643 , PMID: 9450337 , PMID: 21397014 ) (https://link.springer.com/chapter/10.1007/978-1-4612-3084-7_7) (https://escholarship.org/uc/item/1bf1b5m3). Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria (PMID: 13610897 ). IAA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Using material extracted from human urine, it was discovered by Kogl in 1933 that indoleacetic acid is also an important plant hormone (PMID: 13610897 ). Specifically, IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan (Wikipedia). IAA and some derivatives can be oxidized by horseradish peroxidase (HRP) into cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy (PMID: 11163327 ).
Structure
Data?1582752115
Synonyms
ValueSource
(indol-3-yl)AcetateChEBI
(indol-3-yl)Acetic acidChEBI
2-(indol-3-yl)Ethanoic acidChEBI
3-IndolylessigsaeureChEBI
HeteroauxinChEBI
IAAChEBI
IESChEBI
Indole-3-acetic acidKegg
IndoleacetateKegg
(1H-indol-3-yl)AcetateKegg
2-(indol-3-yl)EthanoateGenerator
Indole-3-acetateGenerator
(1H-indol-3-yl)Acetic acidGenerator
(1H-indol-3-yl)-AcetateHMDB
(1H-indol-3-yl)-Acetic acidHMDB
1H-indol-3-YlacetateHMDB
1H-indol-3-Ylacetic acidHMDB
1H-Indole-3-acetateHMDB
1H-Indole-3-acetic acidHMDB
2-(1H-indol-3-yl)AcetateHMDB
2-(1H-indol-3-yl)Acetic acidHMDB
2-(3-Indolyl)acetateHMDB
2-(3-Indolyl)acetic acidHMDB
3-(Carboxymethyl)indoleHMDB
3-IAAHMDB
3-Indole-acetic acidHMDB
3-IndoleacetateHMDB
3-Indoleacetic acidHMDB
3-IndolylacetateHMDB
3-Indolylacetic acidHMDB
alpha-indol-3-yl-Acetic acidHMDB
b-IndoleacetateHMDB
b-Indoleacetic acidHMDB
b-IndolylacetateHMDB
b-Indolylacetic acidHMDB
beta-Indole-3-acetic acidHMDB
beta-IndoleacetateHMDB
beta-Indoleacetic acidHMDB
beta-IndolylacetateHMDB
beta-Indolylacetic acidHMDB
indol-3-YlacetateHMDB
indol-3-Ylacetic acidHMDB
Indolyl-3-acetateHMDB
Indolyl-3-acetic acidHMDB
IndolylacetateHMDB
Indolylacetic acidHMDB
Kyselina 3-indolyloctovaHMDB
RhizopinHMDB
Rhizopon aHMDB
Skatole carboxylateHMDB
Skatole carboxylic acidHMDB
Indoleacetic acid, calcium saltHMDB
Indoleacetic acid, monopotassium saltHMDB
Indoleacetic acid, monosodium saltHMDB
IES CPDHMDB
Indole acetic acidHMDB
Indoleacetic acid, alpha-(14)C-labeledHMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)HMDB
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)HMDB
3,3'-Dithiobis-L-alanineHMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfideHMDB
beta,Beta'-dithiodialanineHMDB
Bis(beta-amino-beta-carboxyethyl) disulfideHMDB
e921HMDB
L-alpha-Diamino-beta-dithiolactic acidHMDB
L-DicysteineHMDB
Oxidized L-cysteineHMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoate)HMDB
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)HMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfideHMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphideHMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphideHMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfideHMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphideHMDB
b,Beta'-dithiodialanineHMDB
Β,beta'-dithiodialanineHMDB
Bis(b-amino-b-carboxyethyl) disulfideHMDB
Bis(b-amino-b-carboxyethyl) disulphideHMDB
Bis(beta-amino-beta-carboxyethyl) disulphideHMDB
Bis(β-amino-β-carboxyethyl) disulfideHMDB
Bis(β-amino-β-carboxyethyl) disulphideHMDB
L-a-Diamino-b-dithiolactateHMDB
L-a-Diamino-b-dithiolactic acidHMDB
L-alpha-Diamino-beta-dithiolactateHMDB
L-Α-diamino-β-dithiolactateHMDB
L-Α-diamino-β-dithiolactic acidHMDB
(-)-CystineHMDB
(R-(R*,r*))-3,3'-dithiobisHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoateHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acidHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoateHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acidHMDB
3,3'-DithiobisHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoateHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acidHMDB
3,3'-DithiodialanineHMDB
b,B'-diamino-b,b'-dicarboxydiethyl disulfideHMDB
b,B'-dithiodialanineHMDB
beta,Beta'-dithiobisalanineHMDB
Bis(b-amino-beta-carboxyethyl) disulfideHMDB
Cysteine disulfideHMDB
CystinHMDB
CystineHMDB
Cystine acidHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoateHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoic acidHMDB
DicysteineHMDB
GelucystineHMDB
L-(-)-CystineHMDB
L-Cysteine disulfideHMDB
L-CystinHMDB
[R-(R*,r*)]-3,3'-dithiobisHMDB
L CystineHMDB
Copper cystinateHMDB
(+)-Lactic acidHMDB
(S)-(+)-Lactic acidHMDB
(S)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxypropionic acidHMDB
L-(+)-alpha-Hydroxypropionic acidHMDB
L-(+)-Lactic acidHMDB
L-MilchsaeureHMDB
L-LactateHMDB
(+)-LactateHMDB
(S)-(+)-LactateHMDB
(S)-2-HydroxypropanoateHMDB
(S)-2-HydroxypropionateHMDB
L-(+)-a-HydroxypropionateHMDB
L-(+)-a-Hydroxypropionic acidHMDB
L-(+)-alpha-HydroxypropionateHMDB
L-(+)-Α-hydroxypropionateHMDB
L-(+)-Α-hydroxypropionic acidHMDB
L-(+)-LactateHMDB
(alpha)-LactateHMDB
(alpha)-Lactic acidHMDB
(S)-(+)-2-HydroxypropanoateHMDB
(S)-(+)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxy-propanoateHMDB
(S)-2-Hydroxy-propanoic acidHMDB
(S)-LactateHMDB
(S)-Lactic acidHMDB
1-Hydroxyethane 1-carboxylateHMDB
1-Hydroxyethane 1-carboxylic acidHMDB
1-HydroxyethanecarboxylateHMDB
1-Hydroxyethanecarboxylic acidHMDB
2-HydroxypropanoateHMDB
2-Hydroxypropanoic acidHMDB
2-HydroxypropionateHMDB
a-HydroxypropanoateHMDB
a-Hydroxypropanoic acidHMDB
a-HydroxypropionateHMDB
a-Hydroxypropionic acidHMDB
alpha-HydroxypropanoateHMDB
alpha-Hydroxypropanoic acidHMDB
alpha-HydroxypropionateHMDB
alpha-Hydroxypropionic acidHMDB
L-(+)- Lactic acidHMDB
L-2-HydroxypropanoateHMDB
L-2-Hydroxypropanoic acidHMDB
LactateHMDB
Lactic acidHMDB
Milk acidHMDB
Sarcolactic acidHMDB
2-Hydroxypropionic acidHMDB
D-Lactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
9-beta-D-Ribofuranosyl-9H-purin-6-olHMDB
9-beta-D-RibofuranosylhypoxanthineHMDB
Hypoxanthine D-ribosideHMDB
HypoxanthosineHMDB
iHMDB
InosinHMDB
InosinaHMDB
InosinumHMDB
InotinHMDB
9-b-D-Ribofuranosyl-9H-purin-6-olHMDB
9-Β-D-ribofuranosyl-9H-purin-6-olHMDB
9-b-D-RibofuranosylhypoxanthineHMDB
9-Β-D-ribofuranosylhypoxanthineHMDB
(-)-InosineHMDB
1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-oneHMDB
9-b-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-RibofuranosylhypoxanthineHMDB
9beta-D-RibofuranosylhypoxanthineHMDB
9beta-delta-RibofuranosylhypoxanthineHMDB
AtorelHMDB
beta-D-Ribofuranoside hypoxanthine-9HMDB
beta-delta-Ribofuranoside hypoxanthine-9HMDB
beta-InosineHMDB
HXRHMDB
Hypoxanthine 9-beta-D-ribofuranosideHMDB
Hypoxanthine 9-beta-delta-ribofuranosideHMDB
Hypoxanthine nucleosideHMDB
Hypoxanthine ribonucleosideHMDB
Hypoxanthine ribosideHMDB
Hypoxanthine-9 beta-D-ribofuranosideHMDB
Hypoxanthine-9 beta-delta-ribofuranosideHMDB
Hypoxanthine-9-beta-D-ribofuranosideHMDB
Hypoxanthine-9-beta-delta-ribofuranosideHMDB
Hypoxanthine-9-D-ribofuranosideHMDB
Hypoxanthine-9-delta-ribofuranosideHMDB
Hypoxanthine-riboseHMDB
Indole-3-carboxaldehydeHMDB
InoHMDB
InosieHMDB
Iso-prinosineHMDB
OxiaminHMDB
Panholic-LHMDB
Pantholic-LHMDB
RibonosineHMDB
SelferHMDB
TrophicardylHMDB
(2S)-6-(Acetylamino)-2-aminohexanoic acidHMDB
N(6)-ACETYLLYSINEHMDB
N(zeta)-AcetyllysineHMDB
N-epsilon-Acetyl-L-lysineHMDB
N-Epsilon-AcetyllysineHMDB
N(epsilon)-Acetyl-L-lysineHMDB
N(zeta)-Acetyl-L-lysineHMDB
(2S)-6-(Acetylamino)-2-aminohexanoateHMDB
N(Z)-AcetyllysineHMDB
N(Ζ)-acetyllysineHMDB
N(Z)-Acetyl-L-lysineHMDB
N(Ζ)-acetyl-L-lysineHMDB
e-Acetyl-L-lysineHMDB
e-N-Acetyl-L-lysineHMDB
e-N-AcetyllysineHMDB
epsilon-Acetyl-L-lysineHMDB
epsilon-N-Acetyl-L-lysineHMDB
epsilon-N-AcetyllysineHMDB
L-e-N-AcetyllysineHMDB
L-epsilon-N-AcetyllysineHMDB
N-e-Acetyl-L-lysineHMDB
N-e-AcetyllysineHMDB
N6-AcetyllysineHMDB
Ne-acetyl-L-lysineHMDB
Ne-acetyllysineHMDB
Omega-N-acetyl-L-lysineHMDB
W-N-Acetyl-L-lysineHMDB
N(6)-AcetyllsineHMDB
Omega-acetyllsineHMDB
beta-Alanyl-3-methyl-L-histidineHMDB
beta-Alanyl-N(pai)-methyl-L-histidineHMDB
b-Alanyl-3-methyl-L-histidineHMDB
Β-alanyl-3-methyl-L-histidineHMDB
b-Alanyl-N(pai)-methyl-L-histidineHMDB
Β-alanyl-N(pai)-methyl-L-histidineHMDB
L-AnserineHMDB
L-N-b-Alanyl-3-methyl-histidineHMDB
L-N-beta-Alanyl-3-methyl-histidineHMDB
N-b-Alanyl-3-methyl-L-histidineHMDB
N-beta-Alanyl-3-methyl-L-histidineHMDB
BalanineHMDB
Beta Alanyl 3 methylhistidineHMDB
Beta-Alanyl-3-methylhistidineHMDB
OphidineHMDB
Indoleacetic acidChEBI
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name2-(1H-indol-3-yl)acetic acid
Traditional Nameβ-indole-3-acetic acid
CAS Registry Number87-51-4
SMILES
OC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
InChI KeySEOVTRFCIGRIMH-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 mg/mLNot Available
LogP1.41HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP1.87ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0391000000-7581f14fe5be5b2b2954Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0691000000-de9ac4f748d50db109eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0591000000-9687f83d1372abe23c3cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-1793100000-7c78003038436ec5a902Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00ai-7910000000-4aa7b8244f32048c76bcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0fk9-9250000000-a5f931fc3292056dba65Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-1920000000-f0ecee61454a589493afSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1692000000-ce863a1ca2a657cb41d5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-0900000000-1edcb4977a52155bc130Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0391000000-7581f14fe5be5b2b2954Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0691000000-de9ac4f748d50db109eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0591000000-9687f83d1372abe23c3cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1793100000-7c78003038436ec5a902Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ai-7910000000-4aa7b8244f32048c76bcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9250000000-a5f931fc3292056dba65Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1920000000-f0ecee61454a589493afSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1692000000-ce863a1ca2a657cb41d5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0691000000-f6073f8f35a6930b5aacSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-1900000000-ab74ec83b16ac0b97d12Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-7920000000-8dab2ad22251c9fbd21cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00e9-0900000000-187b48f2258823cbc6a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-30b7a73fa446d0e3c8d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0900000000-bbe0fb5a48f89ea6e383Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0900000000-97850f400d80de278334Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-600545759ef108827b9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-b735e95cb23091491c2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00e9-0900000000-187b48f2258823cbc6a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-7dd685d97c3fa897c28fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-5e0acffe0e3e18677dbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-97850f400d80de278334Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-600545759ef108827b9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-b735e95cb23091491c2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-f6dbb01a35af3042d126Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2ae231b7d0e2cd50aed8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-6900000000-9eae14faa16b8f8259daSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-003r-0900000000-1edcb4977a52155bc130Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0kxr-5900000000-ba2eed29832f9ee48921Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004l-5900000000-a0b30710f83e53b6f3dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9500000000-146ac0a20f9d53e76291Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053r-9600000000-d9258b3c6b5c6f748f6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9300000000-b59628beb41b424daf4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , Positive (Annotated)splash10-004i-0900000000-755373c9248cfb6425fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-2b3df7a1dd85faea6705Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-003r-0900000000-9522ab089ab89b64f96aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0900000000-45eab4ddd1395448f757Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-3ffc47eb6c977956ad93Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Central Nervous System
  • Fibroblasts
  • Hippocampus
  • Hypothalamus
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Spinal Cord
  • Striatum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.85 +/- 1.71 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.100 +/- 0.100 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.05 (0.0-0.118) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.05 (0.0- 0.1) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.03 (0.005 - 0.3) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0359 +/- 0.0150 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0280 +/- 0.0127 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.339 +/- 0.0743 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0251 +/- 0.00211 uMNot SpecifiedNot SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified0.859 +/- 2.16 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.08 +/- 1.40 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.151 +/- 0.478 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.14 +/- 3.16 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified10.213 +/- 8.547 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.03-1.95 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.22(0.06-1.18) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.28(0.02-1.98) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified41.027 +/- 21.106 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified24.75 +/- 16.978 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.4 (1.8-6.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.0 +/- 1.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.944 (0.457-1.294) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.5-2.8 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.2 (0.1-31.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified4.6 (0.1-5.7) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified3.4 (1.3-12.3) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.8 (0.1-5.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified3.8 (1.1-8.4) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified1.5-2.6 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified5.6 (5.5 - 5.8) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.6(0.6-5.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.70 +/- 12.56 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified5 +/- 3.200 uMAdult (>18 years old)Both
Uremia
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0251 +/- 0.00240 uMNot SpecifiedNot Specifiedanorexia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0315 +/- 0.00748 uMChildren (1-13 years old)Bothautism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0299 +/- 0.00280 uMNot SpecifiedNot Specifieddepressive details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0247 +/- 0.00360 uMNot SpecifiedNot SpecifiedMania details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0337 +/- 0.00457 uMNot SpecifiedNot SpecifiedRetarded depression details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Not SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Children (1-13 years old)BothEnthesitis-related arthritis details
SalivaDetected but not Quantified Adult (>18 years old)MaleTooth Decay details
SalivaDetected and Quantified0.571 +/- 0.992 uMAdult (>18 years old)BothDental caries
    • Sugimoto et al. (...
details
UrineDetected and Quantified11.58 +/- 10.413 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified45.731 +/- 33.914 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified64.967 +/- 50.993 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified42.755 +/- 34.674 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified33.666 +/- 20.269 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.0 (2.5-6.8) umol/mmol creatinineAdult (>18 years old)BothIrritable bowel syndrome (IBS) details
UrineDetected and Quantified1.636-2.0930 umol/mmol creatinineChildren (1-13 years old)FemaleTryptophanuria with dwarfism details
UrineDetected and Quantified6.165 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified3.5 +/- 0.33 umol/mmol creatinineAdult (>18 years old)Both
Appendicitis
details
UrineDetected and Quantified3.1 +/- 0.14 umol/mmol creatinineAdult (>18 years old)Both
Appendicitis
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Anorexia nervosa
  1. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
Autism
  1. Anderson GM, Ross DL, Klykylo W, Feibel FC, Cohen DJ: Cerebrospinal fluid indoleacetic acid in autistic subjects. J Autism Dev Disord. 1988 Jun;18(2):259-62. [PubMed:3410814 ]
Major depressive disorder
  1. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Appendicitis
  1. 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 ]
Irritable bowel syndrome
  1. Bearcroft CP, Perrett D, Farthing MJ: Postprandial plasma 5-hydroxytryptamine in diarrhoea predominant irritable bowel syndrome: a pilot study. Gut. 1998 Jan;42(1):42-6. [PubMed:9505884 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Tryptophanuria with dwarfism
  1. TADA K, ITO H, WADA Y, ARAKAWA T: CONGENITAL TRYPTOPHANURIA WITH DWARFISM ("H" DISEASE-LIKE CLINICAL FEATURES WITHOUT INDICANURIA AND GENERALIZED AMINOACIDURIA):--A PROBABLY NEW INBORN ERROR OF TRYPTOPHAN METABOLISM. Tohoku J Exp Med. 1963 Jul 25;80:118-34. [PubMed:14055140 ]
Associated OMIM IDs
DrugBank IDDB07950
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030920
KNApSAcK IDC00000100
Chemspider ID780
KEGG Compound IDC00954
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndole-3-acetic_acid
METLIN IDNot Available
PubChem Compound802
PDB IDNot Available
ChEBI ID16411
Food Biomarker OntologyNot Available
VMH IDIND3AC
References
Synthesis Reference Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:12589387 ]
  2. 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 ]
  3. Tu JB, Wong CY: Serotonin metabolism in normal and abnormal infants during the perinatal period. Biol Neonate. 1976;29(3-4):187-93. [PubMed:133735 ]
  4. Blennow K, Wallin A, Gottfries CG, Mansson JE, Svennerholm L: Concentration gradients for monoamine metabolites in lumbar cerebrospinal fluid. J Neural Transm Park Dis Dement Sect. 1993;5(1):5-15. [PubMed:7679905 ]
  5. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  6. Morgan WW, Grant RW: Increased rate of disappearance of serum probenecid in barbital dependent rats. Eur J Pharmacol. 1976 Dec;40(2):349-57. [PubMed:1033074 ]
  7. Jellinger K, Riederer P: Brain monoamines in metabolic (endotoxic) coma. A preliminary biochemical study in human postmortem material. J Neural Transm. 1977;41(4):275-86. [PubMed:925688 ]
  8. Sarrias MJ, Cabre P, Martinez E, Artigas F: Relationship between serotoninergic measures in blood and cerebrospinal fluid simultaneously obtained in humans. J Neurochem. 1990 Mar;54(3):783-6. [PubMed:1689378 ]
  9. Kema IP, Meijer WG, Meiborg G, Ooms B, Willemse PH, de Vries EG: Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection. Clin Chem. 2001 Oct;47(10):1811-20. [PubMed:11568091 ]
  10. Bai F, Jones DC, Lau SS, Monks TJ: Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. Chem Res Toxicol. 2001 Jul;14(7):863-70. [PubMed:11453733 ]
  11. Ridges AP, Bishop FM, Lawton K, Goldberg IJ: Amine metabolism, thyroid function and response to clomipramine and maprotiline medication in depression. Postgrad Med J. 1980;56 Suppl 1:37-41. [PubMed:6156444 ]
  12. Raghuram TC, Krishnaswamy K: Serotonin metabolism is pellagra. Arch Neurol. 1975 Oct;32(10):708-10. [PubMed:1180737 ]
  13. Carling RS, Degg TJ, Allen KR, Bax ND, Barth JH: Evaluation of whole blood serotonin and plasma and urine 5-hydroxyindole acetic acid in diagnosis of carcinoid disease. Ann Clin Biochem. 2002 Nov;39(Pt 6):577-82. [PubMed:12564839 ]
  14. Taniguchi K, Okatani Y, Sagara Y: Serotonin metabolism in the fetus in preeclampsia. Asia Oceania J Obstet Gynaecol. 1994 Mar;20(1):77-86. [PubMed:7513511 ]
  15. Russo S, Boon JC, Kema IP, Willemse PH, den Boer JA, Korf J, de Vries EG: Patients with carcinoid syndrome exhibit symptoms of aggressive impulse dysregulation. Psychosom Med. 2004 May-Jun;66(3):422-5. [PubMed:15184706 ]
  16. Igari T, Shimamura T: Serotonin metabolism and its enzymic activities in joint diseases. Clin Orthop Relat Res. 1979 Mar-Apr;(139):232-49. [PubMed:455840 ]
  17. Bearcroft CP, Perrett D, Farthing MJ: Postprandial plasma 5-hydroxytryptamine in diarrhoea predominant irritable bowel syndrome: a pilot study. Gut. 1998 Jan;42(1):42-6. [PubMed:9505884 ]
  18. 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 ]
  19. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]
  20. Apak S, Kazez A, Ozel SK, Ustundag B, Akpolat N, Kizirgil A: Spot urine 5-hydroxyindoleacetic acid levels in the early diagnosis of acute appendicitis. J Pediatr Surg. 2005 Sep;40(9):1436-9. [PubMed:16150345 ]
  21. WEISSBACH H, KING W, SJOERDSMA A, UDENFRIEND S: Formation of indole-3-acetic acid and tryptamine in animals: a method for estimation of indole-3-acetic acid in tissues. J Biol Chem. 1959 Jan;234(1):81-6. [PubMed:13610897 ]
  22. Folkes LK, Wardman P: Oxidative activation of indole-3-acetic acids to cytotoxic species- a potential new role for plant auxins in cancer therapy. Biochem Pharmacol. 2001 Jan 15;61(2):129-36. [PubMed:11163327 ]
  23. Finegold SM, Molitoris D, Song Y, Liu C, Vaisanen ML, Bolte E, McTeague M, Sandler R, Wexler H, Marlowe EM, Collins MD, Lawson PA, Summanen P, Baysallar M, Tomzynski TJ, Read E, Johnson E, Rolfe R, Nasir P, Shah H, Haake DA, Manning P, Kaul A: Gastrointestinal microflora studies in late-onset autism. Clin Infect Dis. 2002 Sep 1;35(Suppl 1):S6-S16. doi: 10.1086/341914. [PubMed:12173102 ]
  24. Idris EE, Iglesias DJ, Talon M, Borriss R: Tryptophan-dependent production of indole-3-acetic acid (IAA) affects level of plant growth promotion by Bacillus amyloliquefaciens FZB42. Mol Plant Microbe Interact. 2007 Jun;20(6):619-26. doi: 10.1094/MPMI-20-6-0619. [PubMed:17555270 ]
  25. Patten CL, Glick BR: Role of Pseudomonas putida indoleacetic acid in development of the host plant root system. Appl Environ Microbiol. 2002 Aug;68(8):3795-801. [PubMed:12147474 ]
  26. Barash I, Manulis-Sasson S: Recent evolution of bacterial pathogens: the gall-forming Pantoea agglomerans case. Annu Rev Phytopathol. 2009;47:133-52. doi: 10.1146/annurev-phyto-080508-081803. [PubMed:19400643 ]
  27. Glickmann E, Gardan L, Jacquet S, Hussain S, Elasri M, Petit A, Dessaux Y: Auxin production is a common feature of most pathovars of Pseudomonas syringae. Mol Plant Microbe Interact. 1998 Feb;11(2):156-62. doi: 10.1094/MPMI.1998.11.2.156. [PubMed:9450337 ]
  28. Kochar M, Upadhyay A, Srivastava S: Indole-3-acetic acid biosynthesis in the biocontrol strain Pseudomonas fluorescens Psd and plant growth regulation by hormone overexpression. Res Microbiol. 2011 May;162(4):426-35. doi: 10.1016/j.resmic.2011.03.006. Epub 2011 Mar 23. [PubMed:21397014 ]
  29. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  30. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

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
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
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
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
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
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
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
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
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
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails