indole-3-acetate (PAMDB120116)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120116
Identification
Name: indole-3-acetate
Description:An indol-3-yl carboxylic acid anion that is the conjugate base of indole-3-acetic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (indol-3-yl)acetate
  • 2-(indol-3-yl)ethanoate
Chemical Formula: C10H8NO2
Average Molecular Weight: 174.179
Monoisotopic Molecular Weight: 175.06332
InChI Key: SEOVTRFCIGRIMH-UHFFFAOYSA-M
InChI: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)/p-1
CAS number: 87-51-4
IUPAC Name:1H-indol-3-ylacetate
Traditional IUPAC Name: ?-indole-3-acetic acid
SMILES:C([O-])(=O)CC1(=CNC2(C=CC=CC1=2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Indoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct Parent Indole-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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 168.5 °C
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.45 m3·mol-1ChemAxon
Polarizability17.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
indole-3-acetamide + Water → indole-3-acetate + Ammonium
methyl (indol-3-yl)acetate + Water → Hydrogen ion + indole-3-acetate + Methanol
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0391000000-7581f14fe5be5b2b2954View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0691000000-de9ac4f748d50db109eaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-0591000000-9687f83d1372abe23c3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0udi-1793100000-7c78003038436ec5a902View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00ai-7910000000-4aa7b8244f32048c76bcView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0fk9-9250000000-a5f931fc3292056dba65View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-1920000000-f0ecee61454a589493afView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1692000000-ce863a1ca2a657cb41d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-f6dbb01a35af3042d126View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2ae231b7d0e2cd50aed8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-6900000000-9eae14faa16b8f8259daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-003r-0900000000-1edcb4977a52155bc130View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00e9-0900000000-187b48f2258823cbc6a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-30b7a73fa446d0e3c8d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0900000000-bbe0fb5a48f89ea6e383View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0900000000-97850f400d80de278334View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-600545759ef108827b9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0kxr-5900000000-ba2eed29832f9ee48921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004l-5900000000-a0b30710f83e53b6f3dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9500000000-146ac0a20f9d53e76291View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053r-9600000000-d9258b3c6b5c6f748f6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9300000000-b59628beb41b424daf4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , Positive (Annotated)splash10-004i-0900000000-755373c9248cfb6425fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-2b3df7a1dd85faea6705View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-003r-0900000000-9522ab089ab89b64f96aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-b735e95cb23091491c2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2a3dd24f136523e6ce1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-77436493836245345cb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-1900000000-4e0b6f24d03c0b25800fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-0900000000-1d045a56f3669a1c9391View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ai-0900000000-518778c36bacbf77b901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-3900000000-323fc64084836756be30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2a3dd24f136523e6ce1eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-3ffc47eb6c977956ad93View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • 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. [3500530 ]
  • 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. [12589387 ]
  • 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. [7508830 ]
  • Tu JB, Wong CY: Serotonin metabolism in normal and abnormal infants during the perinatal period. Biol Neonate. 1976;29(3-4):187-93. [133735 ]
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  • Morgan WW, Grant RW: Increased rate of disappearance of serum probenecid in barbital dependent rats. Eur J Pharmacol. 1976 Dec;40(2):349-57. [1033074 ]
  • 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. [925688 ]
  • 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. [1689378 ]
  • 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. [11568091 ]
  • 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. [11453733 ]
  • 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. [6156444 ]
  • Raghuram TC, Krishnaswamy K: Serotonin metabolism is pellagra. Arch Neurol. 1975 Oct;32(10):708-10. [1180737 ]
  • 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. [12564839 ]
  • Taniguchi K, Okatani Y, Sagara Y: Serotonin metabolism in the fetus in preeclampsia. Asia Oceania J Obstet Gynaecol. 1994 Mar;20(1):77-86. [7513511 ]
  • 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. [15184706 ]
  • Igari T, Shimamura T: Serotonin metabolism and its enzymic activities in joint diseases. Clin Orthop Relat Res. 1979 Mar-Apr;(139):232-49. [455840 ]
  • 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. [9505884 ]
  • 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. [11462886 ]
  • 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. [16150345 ]
  • 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. [13610897 ]
  • 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. [11163327 ]
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)
External Links:
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METABOLIGHTSMTBLC30854
HMDBHMDB00197
CHEMSPIDER779
PUBCHEM801
CHEBI30854
LIGAND-CPDC00954
CAS87-51-4