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Human Metabolome Database Version 3.5

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Showing metabocard for Indole (HMDB00738)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:13 -0700
HMDB ID HMDB00738
Secondary Accession Numbers None
Metabolite Identification
Common Name Indole
Description Indole 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Azaindene
  2. 1-Benzazole
  3. 2,3-Benzopyrrole
  4. Benzo[b]pyrrole
  5. Indole
  6. Ketole
Chemical Formula C8H7N
Average Molecular Weight 117.1479
Monoisotopic Molecular Weight 117.057849229
IUPAC Name 1H-indole
Traditional IUPAC Name indole
CAS Registry Number 120-72-9
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 Key SIKJAQJRHWYJAI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class N/A
Other Descriptors
  • an indole(Cyc)
  • indole(ChEBI)
  • polycyclic heteroarene(ChEBI)
Substituents
  • Pyrrole
Direct Parent Indoles
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 52.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.56 mg/mL Not Available
LogP 2.14 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 5.31 g/L ALOGPS
LogP 2.29 ALOGPS
LogP 2.07 ChemAxon
LogS -1.34 ALOGPS
pKa (strongest acidic) 16.44 ChemAxon
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 15.79 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 37.14 ChemAxon
Polarizability 12.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (MX-1303)
MS/MS Spectrum EI-B (Unknown)
MS/MS Spectrum EI-B (HITACHI M-68)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Neuron
  • Epidermis
  • Nerve Cells
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Breast cancer Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB04532 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012008
KNApSAcK ID C00001418 Link_out
Chemspider ID 776 Link_out
KEGG Compound ID C00463 Link_out
BioCyc ID INDOLE Link_out
BiGG ID Not Available
Wikipedia Link Indole Link_out
NuGOwiki Link HMDB00738 Link_out
Metagene Link HMDB00738 Link_out
METLIN ID 286 Link_out
PubChem Compound 798 Link_out
PDB ID IND Link_out
ChEBI ID 16881 Link_out
References
Synthesis Reference Grigoleit, Georg; Oberkobusch, Rudolf; Collin, Gerd. Indole from 2-ethylaniline. Ger. Offen. (1973), 6 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 1158878 Link_out
  2. 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. Pubmed: 7040445 Link_out
  3. 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. Pubmed: 9209775 Link_out
  4. Scott AK: Sumatriptan clinical pharmacokinetics. Clin Pharmacokinet. 1994 Nov;27(5):337-44. Pubmed: 7851052 Link_out
  5. 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. Pubmed: 15566297 Link_out
  6. 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. Pubmed: 2229345 Link_out
  7. 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. Pubmed: 8861801 Link_out
  8. 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. Pubmed: 10681668 Link_out
  9. 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. Pubmed: 12663078 Link_out
  10. Yoshida M, Mishiro Y: [Indole production in human whole saliva] Shigaku. 1989 Aug;77(2):472-86. Pubmed: 2489307 Link_out
  11. Freedman DX, Belendiuk K, Belendiuk GW, Crayton JW: Blood tryptophan metabolism in chronic schizophrenics. Arch Gen Psychiatry. 1981 Jun;38(6):655-9. Pubmed: 7247628 Link_out
  12. 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. Pubmed: 11119776 Link_out
  13. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. Pubmed: 6085021 Link_out