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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:00 UTC

Update Date

2023-02-21 17:22:52 UTC

HMDB ID

HMDB0032967

Secondary Accession Numbers

HMDB32967

Metabolite Identification

Common Name

2,4-Dimethyl-1H-indole

Description

2,4-Dimethyl-1H-indole 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. 2,4-Dimethyl-1H-indole has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make 2,4-dimethyl-1H-indole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,4-Dimethyl-1H-indole.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4-Dimethylindole	HMDB

Chemical Formula

C₁₀H₁₁N

Average Molecular Weight

145.201

Monoisotopic Molecular Weight

145.089149357

IUPAC Name

2,4-dimethyl-1H-indole

Traditional Name

2,4-dimethyl-1H-indole

CAS Registry Number

10299-61-3

SMILES

CC1=CC2=C(C)C=CC=C2N1

InChI Identifier

InChI=1S/C10H11N/c1-7-4-3-5-10-9(7)6-8(2)11-10/h3-6,11H,1-2H3

InChI Key

YBUMNVFXMLIKDZ-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032967)
Cell membrane (HMDB: HMDB0032967)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032967)

Source

Exogenous

Exogenous (HMDB: HMDB0032967)

Food

Food (HMDB: HMDB0032967)

Plant (HMDB: HMDB0032967)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032967)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	162.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	2.94	ALOGPS
logP	2.78	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	17	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	47.34 m³·mol⁻¹	ChemAxon
Polarizability	17.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.531	31661259
DarkChem	[M-H]-	130.307	31661259
DeepCCS	[M+H]+	127.116	30932474
DeepCCS	[M-H]-	123.285	30932474
DeepCCS	[M-2H]-	160.474	30932474
DeepCCS	[M+Na]+	135.887	30932474
AllCCS	[M+H]+	125.9	32859911
AllCCS	[M+H-H2O]+	121.1	32859911
AllCCS	[M+NH4]+	130.4	32859911
AllCCS	[M+Na]+	131.7	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.3	32859911
AllCCS	[M+HCOO]-	130.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.55 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3084 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2331.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	529.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	342.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	662.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	546.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1128.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	505.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1397.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	478.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	440.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	29.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Dimethyl-1H-indole	CC1=CC2=C(C)C=CC=C2N1	2507.1	Standard polar	33892256
2,4-Dimethyl-1H-indole	CC1=CC2=C(C)C=CC=C2N1	1445.5	Standard non polar	33892256
2,4-Dimethyl-1H-indole	CC1=CC2=C(C)C=CC=C2N1	1469.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Dimethyl-1H-indole,1TMS,isomer #1	CC1=CC=CC2=C1C=C(C)N2[Si](C)(C)C	1627.4	Semi standard non polar	33892256
2,4-Dimethyl-1H-indole,1TMS,isomer #1	CC1=CC=CC2=C1C=C(C)N2[Si](C)(C)C	1550.5	Standard non polar	33892256
2,4-Dimethyl-1H-indole,1TBDMS,isomer #1	CC1=CC=CC2=C1C=C(C)N2[Si](C)(C)C(C)(C)C	1884.1	Semi standard non polar	33892256
2,4-Dimethyl-1H-indole,1TBDMS,isomer #1	CC1=CC=CC2=C1C=C(C)N2[Si](C)(C)C(C)(C)C	1752.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dimethyl-1H-indole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0900000000-a9cb0a672e50b3af9de1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dimethyl-1H-indole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 10V, Positive-QTOF	splash10-0002-0900000000-2791fbf9b6f227eebc3c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 20V, Positive-QTOF	splash10-0002-0900000000-37c61430e4d2e184af69	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 40V, Positive-QTOF	splash10-001i-3900000000-7e9e86ef0dd9966a4bac	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 10V, Negative-QTOF	splash10-0006-0900000000-91531f557553ef51a111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 20V, Negative-QTOF	splash10-0006-0900000000-575fc0e4ce2cf490800b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 40V, Negative-QTOF	splash10-004i-1900000000-8ad876c11428786a9c5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 10V, Positive-QTOF	splash10-0002-0900000000-fed3ed848d08f12d5436	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 20V, Positive-QTOF	splash10-0002-0900000000-31ac5fd386e0642d57bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 40V, Positive-QTOF	splash10-0fc0-4900000000-f5ac32dda236c43c6827	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 10V, Negative-QTOF	splash10-0006-0900000000-4800f4d774d528d5e535	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 20V, Negative-QTOF	splash10-0006-0900000000-4800f4d774d528d5e535	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dimethyl-1H-indole 40V, Negative-QTOF	splash10-0fbc-0900000000-9d398bb04393908c2f04	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010954

KNApSAcK ID

C00023597

Chemspider ID

9172361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10997169

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,4-Dimethyl-1H-indole (HMDB0032967)

MOL for HMDB0032967 (2,4-Dimethyl-1H-indole)

3D MOL for HMDB0032967 (2,4-Dimethyl-1H-indole)

3D SDF for HMDB0032967 (2,4-Dimethyl-1H-indole)

3D-SDF for HMDB0032967 (2,4-Dimethyl-1H-indole)

PDB for HMDB0032967 (2,4-Dimethyl-1H-indole)

3D PDB for HMDB0032967 (2,4-Dimethyl-1H-indole)

SMILES for HMDB0032967 (2,4-Dimethyl-1H-indole)

INCHI for HMDB0032967 (2,4-Dimethyl-1H-indole)

Structure for HMDB0032967 (2,4-Dimethyl-1H-indole)

3D Structure for HMDB0032967 (2,4-Dimethyl-1H-indole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra