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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:53:23 UTC

Update Date

2023-02-21 17:28:12 UTC

HMDB ID

HMDB0040360

Secondary Accession Numbers

HMDB40360

Metabolite Identification

Common Name

2-Acetyl-1-methylpyrrole

Description

2-Acetyl-1-methylpyrrole, also known as N-methyl-2-acetylpyrrole, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 2-Acetyl-1-methylpyrrole is an earthy tasting compound. 2-Acetyl-1-methylpyrrole has been detected, but not quantified in, asparagus (Asparagus officinalis). This could make 2-acetyl-1-methylpyrrole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Acetyl-1-methylpyrrole.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(1-Methyl-1H-pyrrol-2-yl)ethanone	ChEBI
1-(1-Methylpyrrol-2-yl)ethanone	ChEBI
2-Acetyl-N-methylpyrrole	ChEBI
Methyl 1-methylpyrrol-2-yl ketone	ChEBI
N-Methyl-2-acetylpyrrole	ChEBI
2-Acetyl-1-methylpyrrole	ChEBI
1-(1-Methyl-1H-pyrrol-2-yl)-ethanone	HMDB
1H-Pyrrole, 1-methyl-2-acetyl	HMDB
FEMA 3184	HMDB
Ketone, methyl 1-methylpyrrol-2-yl	HMDB

Chemical Formula

C₇H₉NO

Average Molecular Weight

123.1525

Monoisotopic Molecular Weight

123.068413915

IUPAC Name

1-(1-methyl-1H-pyrrol-2-yl)ethan-1-one

Traditional Name

2-acetyl-1-methylpyrrole

CAS Registry Number

932-16-1

SMILES

CN1C=CC=C1C(C)=O

InChI Identifier

InChI=1S/C7H9NO/c1-6(9)7-4-3-5-8(7)2/h3-5H,1-2H3

InChI Key

NZFLWVDXYUGFAV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Substituted pyrrole
N-methylpyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methyl ketone (CHEBI:59982 )
aromatic ketone (CHEBI:59982 )
pyrroles (CHEBI:59982 )

Ontology

Physiological effect

Organoleptic effect

Odor

Earthy

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040360)
Cytoplasm (HMDB: HMDB0040360)

Source

Exogenous

Exogenous (HMDB: HMDB0040360)

Food

Food (HMDB: HMDB0040360)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040360)

Biological role

Nutrient (HMDB: HMDB0040360)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	200.00 to 202.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	11090 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.387 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.42 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.75	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	16.63	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.99 m³·mol⁻¹	ChemAxon
Polarizability	13.31 Å³	ChemAxon
Number of Rings	1	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]+	125.499	31661259
DarkChem	[M-H]-	120.501	31661259
DeepCCS	[M+H]+	131.723	30932474
DeepCCS	[M-H]-	129.493	30932474
DeepCCS	[M-2H]-	165.362	30932474
DeepCCS	[M+Na]+	140.344	30932474
AllCCS	[M+H]+	123.4	32859911
AllCCS	[M+H-H2O]+	118.5	32859911
AllCCS	[M+NH4]+	127.9	32859911
AllCCS	[M+Na]+	129.2	32859911
AllCCS	[M-H]-	123.1	32859911
AllCCS	[M+Na-2H]-	125.2	32859911
AllCCS	[M+HCOO]-	127.6	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. Predicted by Afia on May 17, 2022.	3.5 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2277 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1831.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	479.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	120.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	445.0 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	497.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	522.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1056.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	288.5 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	1107.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	402.0 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	45.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetyl-1-methylpyrrole	CN1C=CC=C1C(C)=O	1597.0	Standard polar	33892256
2-Acetyl-1-methylpyrrole	CN1C=CC=C1C(C)=O	1035.4	Standard non polar	33892256
2-Acetyl-1-methylpyrrole	CN1C=CC=C1C(C)=O	1069.2	Semi 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-Acetyl-1-methylpyrrole GC-MS (Non-derivatized) - 70eV, Positive	splash10-059x-9300000000-32b2a4b2c02c1b477446	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-1-methylpyrrole 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-Acetyl-1-methylpyrrole 10V, Positive-QTOF	splash10-00di-0900000000-e7df577bf263212d3e9a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 20V, Positive-QTOF	splash10-05fr-0900000000-b15178e95ed6abfb12d6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 40V, Positive-QTOF	splash10-056r-9400000000-e42b329d5f59c724e7ab	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 10V, Negative-QTOF	splash10-00di-1900000000-d16c631a7d47dc229fdb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 20V, Negative-QTOF	splash10-00di-1900000000-6f3a10439bf5f641f550	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 40V, Negative-QTOF	splash10-0udi-9200000000-3b8a3f25e50ec4e9b3f8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 10V, Negative-QTOF	splash10-001i-9400000000-d67546ef541c04354598	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 20V, Negative-QTOF	splash10-0089-9300000000-023f60790f87d30c3e21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 40V, Negative-QTOF	splash10-0fal-9000000000-4d0fc1eebc0c33b87f5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 10V, Positive-QTOF	splash10-00di-7900000000-bc07fcb95094b9acc113	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 20V, Positive-QTOF	splash10-0006-9000000000-545552a108b04b3d1b7d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-1-methylpyrrole 40V, Positive-QTOF	splash10-0006-9000000000-6ff22714023045a309d7	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020088

KNApSAcK ID

Not Available

Chemspider ID

55182

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61240

PDB ID

Not Available

ChEBI ID

59982

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035381

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-Acetyl-1-methylpyrrole (HMDB0040360)

MOL for HMDB0040360 (2-Acetyl-1-methylpyrrole)

3D MOL for HMDB0040360 (2-Acetyl-1-methylpyrrole)

3D SDF for HMDB0040360 (2-Acetyl-1-methylpyrrole)

3D-SDF for HMDB0040360 (2-Acetyl-1-methylpyrrole)

PDB for HMDB0040360 (2-Acetyl-1-methylpyrrole)

3D PDB for HMDB0040360 (2-Acetyl-1-methylpyrrole)

SMILES for HMDB0040360 (2-Acetyl-1-methylpyrrole)

INCHI for HMDB0040360 (2-Acetyl-1-methylpyrrole)

Structure for HMDB0040360 (2-Acetyl-1-methylpyrrole)

3D Structure for HMDB0040360 (2-Acetyl-1-methylpyrrole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra