Livestock Metabolome Database: Showing metabocard for 3-Methylindole (LMDB00160)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:40 UTC

Update Date

2016-07-20 20:57:05 UTC

Lmdb

LMDB00160

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Methylindole

Description

3-Methylindole, or skatole, can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous and one of the rings is a pyrrole. This is probably the reason it's so foul smelling. It is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) and sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity that comes from the lone pair electrons on the nitrogen. It is continuous (all atoms in the ring are sp2 hybridized), planar, and follows the 4n+2 rule because it has 10 pi electrons. It can be synthesized through a Fischer indole synthesis which was developed by Emil Fischer.In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. It is a flavoring ingredient. 3-Methylindole is a mildly toxic white crystalline organic compound with chemical formula C9H9N and CAS number 83-34-1. The compound belongs to the indole family and has a methyl substituent in position 3 of the indole ring. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract), beets, and coal tar, and has a strong fecal odor. In low concentrations it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from skato, the Greek word for dung.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3-Methyl-4,5-benzopyrrole	ChEBI
beta-Methylindole	ChEBI
Skatol	ChEBI
b-Methylindole	Generator
Β-methylindole	Generator
3-Methyl-1H-indole	HMDB
3-MI	HMDB
Scatole	HMDB
Skatole	HMDB
3 Methylindole	HMDB
3-Methylindole	ChEBI

Chemical Formula

C₉H₉N

Average Molecular Weight

131.1745

Monoisotopic Molecular Weight

131.073499293

IUPAC Name

3-methyl-1H-indole

Traditional Name

scatole

CAS Registry Number

83-34-1

SMILES

CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

InChI Key

ZFRKQXVRDFCRJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 3-methylindoles. These are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-methylindoles

Alternative Parents

Substituents

3-methylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methylindole (CHEBI:9171 )
a small molecule (SKATOLE )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.58	ALOGPS
logP	2.59	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	17.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.19 m³·mol⁻¹	ChemAxon
Polarizability	14.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-9200000000-251c9585af60abc11fb1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-9200000000-251c9585af60abc11fb1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1900000000-f9bb0d50c5d49c2c6c4a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-a7cd474bc90f9a0227e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-2900000000-cb7f6d8c4ad7b0a1523b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000l-9200000000-e9a200fb7b8fc93ced48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0ufr-9200000000-7120fbb6f78f440ff725	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-002b-9800000000-a8de490dffcbc2cb0c24	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-355610a12cde08bb25c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-36a1bcb0093fec9dd5c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-3900000000-d8aebbf9a6779cddc735	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-ed646ab44a1fcc84725b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-ed6f0939d3598782a893	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f89-2900000000-a801a40b2fcba369d3d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-244a9c7ac26f19950926	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-e7c79bc3a884b9bd7abe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-e057600f7f225ff9cec2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-f53b130d6fbd7a49b7bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-92ee6b9af4d8ea4f32d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-7900000000-f01b3fb9a64effb7bb2e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-2900000000-dba6ed7df0e1ee94cafe	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details