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Bovine Rumen Metabolome Database



Showing metabocard for Indole (RMDB00738)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-10-28 14:02:03
Accession Number RMDB00738
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.
Synonyms
  1. 1-Azaindene
  2. 1-Benzazole
  3. 2,3-Benzopyrrole
  4. Benzo[b]pyrrole
  5. Indole
  6. Ketole
Chemical IUPAC Name 1H-indole
Chemical Formula C8H7N
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Indoles and Indole Derivatives
Sub Class
  • Miscellaneous Indoles
Family
  • Microbial_Metabolite
Species
  • aromatic compound; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 117.148
Monoisotopic Molecular Weight 117.057846
Isomeric SMILES N1C=CC2=C1C=CC=C2
Canonical SMILES N1C=CC2=C1C=CC=C2
KEGG Compound ID C00463 Link Image
BioCyc ID INDOLE Link Image
BiGG ID Not Available
Wikipedia Link Indole Link Image
METLIN ID 286 Link Image
PubChem Compound 798 Link Image
PubChem Substance 3747 Link Image
ChEBI ID 16881 Link Image
CAS Registry Number 120-72-9
InChI Identifier InChI=1/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
Synthesis Reference Grigoleit, Georg; Oberkobusch, Rudolf; Collin, Gerd. Indole from 2-ethylaniline. Ger. Offen. (1973), 6 pp.
Melting Point (Experimental) 52.5 oC
Experimental Water Solubility 3.56 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 5.31 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 2.14 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 2.29 [Predicted by ALOGPS]; 2.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 185L Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 200 +/- 100 uM
Age N/A
Sex Both
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments after feeding tryptophane
References
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image