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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:17 UTC
HMDB IDHMDB00738
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndole
DescriptionIndole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.
Structure
Thumb
Synonyms
ValueSource
2,3-BenzopyrroleChEBI
indolChEBI
INDOLEChEBI
1-AzaindeneHMDB
1-BenzazoleHMDB
benzo[b]PyrroleHMDB
KetoleHMDB
Chemical FormulaC8H7N
Average Molecular Weight117.1479
Monoisotopic Molecular Weight117.057849229
IUPAC Name1H-indole
Traditional Nameindole
CAS Registry Number120-72-9
SMILES
N1C=CC2=C1C=CC=C2
InChI Identifier
InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
InChI KeyInChIKey=SIKJAQJRHWYJAI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.56 mg/mLNot Available
LogP2.14HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.31 mg/mLALOGPS
logP2.29ALOGPS
logP2.07ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.14 m3·mol-1ChemAxon
Polarizability12.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-622dfed80152ea08d52aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-2531cceca05522a5489eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-5e07c15293929ff4440fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-014i-6900000000-09af4d0af4e5f7259a59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-014i-9800000000-4160749bd673d5e00048View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-014i-9800000000-33bf321019a6a8e3401aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0900000000-e6b11e225744a0d85f71View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-9700000000-3b1ec48b5bce79adb282View in MoNA
1D NMR1H 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
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Fibroblasts
  • Intestine
  • Nerve Cells
  • Neuron
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0 - 46.52 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04532
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012008
KNApSAcK IDC00001418
Chemspider ID776
KEGG Compound IDC00463
BioCyc IDINDOLE
BiGG IDNot Available
Wikipedia LinkIndole
NuGOwiki LinkHMDB00738
Metagene LinkHMDB00738
METLIN ID286
PubChem Compound798
PDB IDIND
ChEBI ID16881
References
Synthesis ReferenceGrigoleit, Georg; Oberkobusch, Rudolf; Collin, Gerd. Indole from 2-ethylaniline. Ger. Offen. (1973), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [6085021 ]
  2. Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7. [12663078 ]
  3. Gambhir KK, McMenamy RH, Watson F: Positions in human serum albumin which involve the indole binding site. Sequence of 107-residue fragment. J Biol Chem. 1975 Sep 10;250(17):6711-9. [1158878 ]
  4. Welch DF, Ahlin PA, Matsen JM: Differentiation of Haemophilus spp. in Respiratory isolate cultures by an indole spot test. J Clin Microbiol. 1982 Feb;15(2):216-9. [7040445 ]
  5. Kunka RL, Hussey EK, Shaw S, Warner P, Aubert B, Richard I, Fowler PA, Pakes GE: Safety, tolerability, and pharmacokinetics of sumatriptan suppositories following single and multiple doses in healthy volunteers. Cephalalgia. 1997 Jun;17(4):532-40. [9209775 ]
  6. Scott AK: Sumatriptan clinical pharmacokinetics. Clin Pharmacokinet. 1994 Nov;27(5):337-44. [7851052 ]
  7. Coowar D, Bouissac J, Hanbali M, Paschaki M, Mohier E, Luu B: Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres. J Med Chem. 2004 Dec 2;47(25):6270-82. [15566297 ]
  8. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [2229345 ]
  9. Agatsuma S, Sekino H, Watanabe H: Indoxyl-beta-D-glucuronide and 3-indoxyl sulfate in plasma of hemodialysis patients. Clin Nephrol. 1996 Apr;45(4):250-6. [8861801 ]
  10. Aoyama I, Miyazaki T, Niwa T: Preventive effects of an oral sorbent on nephropathy in rats. Miner Electrolyte Metab. 1999 Jul-Dec;25(4-6):365-72. [10681668 ]
  11. Yoshida M, Mishiro Y: [Indole production in human whole saliva] Shigaku. 1989 Aug;77(2):472-86. [2489307 ]
  12. Freedman DX, Belendiuk K, Belendiuk GW, Crayton JW: Blood tryptophan metabolism in chronic schizophrenics. Arch Gen Psychiatry. 1981 Jun;38(6):655-9. [7247628 ]
  13. Takken W, van Loon JJ, Adam W: Inhibition of host-seeking response and olfactory responsiveness in Anopheles gambiae following blood feeding. J Insect Physiol. 2001 Mar;47(3):303-310. [11119776 ]