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Showing Compound Indole (FDB012008)

Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:57 UTC
Primary IDFDB012008
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIndole
DescriptionConstituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole is a major constituent of coal-tar, and the 220-260 °C distillation fraction is the main industrial source of the material. Indole and its derivatives can also be synthesized by a variety of methods. The main industrial routes start from aniline.; Indole is a solid at room temperature. Indole 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 odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.; 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. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an indole ring are called indoles. The most famous derivative is the amino acid tryptophan.; 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.; The Leimgruber-Batcho indole synthesis is an efficient method of sythesizing indole and substituted indoles. Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. This method is especially popular in the pharmaceutical industry, where many pharmaceutical drugs are made up of specifically substituted indoles.; The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. Indole is found in many foods, some of which are flaxseed, agar, american pokeweed, and pear.
CAS Number120-72-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Azaindenedb_source
1-Benzazoledb_source
1-Benzo(b)pyrrolebiospider
1-H-indolbiospider
1H-Benzo[b]pyrrolebiospider
1H-Indolebiospider
1H-Indole (9CI)biospider
2-Amino-3-hydroxy-3-phenylpropanoic acidbiospider
2, 3-Benzopyrrolebiospider
2,3-Benzopyrolebiospider
2,3-Benzopyrroledb_source
Benzo[b]pyrrolebiospider
Benzopyrrolebiospider
DL-beta-phenylserinebiospider
FEMA 2593db_source
INDbiospider
Indolbiospider
Indol(german)biospider
Indole (8CI)biospider
Indole benzo-pyrrolebiospider
Ketolebiospider
Ketole (obsol.)db_source
Predicted Properties
PropertyValueSource
Water Solubility5.31 g/LALOGPS
logP2.29ALOGPS
logP1.64ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)4.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability12.78 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14N2
IUPAC name1H-indole; 3H-indole
InChI IdentifierInChI=1S/2C8H7N/c2*1-2-4-8-7(3-1)5-6-9-8/h1-4,6H,5H2;1-6,9H
InChI KeyAYVVZVSBYJTFGL-UHFFFAOYSA-N
Isomeric SMILESC1C=NC2=C1C=CC=C2.N1C=CC2=C1C=CC=C2
Average Molecular Weight234.2958
Monoisotopic Molecular Weight234.115698458
Classification
Description Belongs to the class of organic compounds known as indoles. Indoles 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
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 82.02%; H 6.02%; N 11.96%DFC
Melting PointMp 52°DFC
Boiling PointBp5 122.5-124°DFC
Experimental Water Solubility3.56 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.14HANSCH,C ET AL. (1995)
Experimental pKapKa2 16.97 (25°,NH, KOH aq.)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data295 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID776
ChEMBL IDCHEMBL15844
KEGG Compound IDC00463
Pubchem Compound ID798
Pubchem Substance IDNot Available
ChEBI ID16881
Phenol-Explorer IDNot Available
DrugBank IDDB04532
HMDB IDHMDB00738
CRC / DFC (Dictionary of Food Compounds) IDHCM26-E:HCM26-E
EAFUS ID1794
Dr. Duke IDINDOLE
BIGG IDNot Available
KNApSAcK IDC00001418
HET IDIND
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID120-72-9
GoodScent IDrw1006511
SuperScent ID798
Wikipedia IDIndole
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti-acne50177 An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti cariogenic52217 An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.DUKE
Anti-salmonella33282 An agent that targets and eliminates Salmonella bacteria, reducing the risk of food poisoning and gastrointestinal infections. Therapeutically, it is used to treat salmonellosis, a disease caused by Salmonella infection, and to prevent outbreaks in high-risk individuals, such as those with weakened immune systems.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
Insectiphile24852 A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Tumorigenic50903 An agent or factor that promotes tumor formation and growth, playing a key role in cancer development. Therapeutically, understanding tumorigenic mechanisms informs cancer treatment strategies, with applications in oncology for developing targeted therapies to inhibit tumor growth and progression.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mothball
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
burnt
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
jasmine
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
honey
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fishy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
animal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
moth ball
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fecal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
naphthelene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.