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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:22:42 UTC

Update Date

2023-02-21 17:27:14 UTC

HMDB ID

HMDB0039840

Secondary Accession Numbers

HMDB39840

Metabolite Identification

Common Name

3-(1-Pyrrolidinyl)-2-butanone

Description

3-(1-Pyrrolidinyl)-2-butanone belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Based on a literature review very few articles have been published on 3-(1-Pyrrolidinyl)-2-butanone.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1'-Pyrrolidinyl)-2-butanone	HMDB

Chemical Formula

C₈H₁₅NO

Average Molecular Weight

141.2108

Monoisotopic Molecular Weight

141.115364107

IUPAC Name

3-(pyrrolidin-1-yl)butan-2-one

Traditional Name

3-(pyrrolidin-1-yl)butan-2-one

CAS Registry Number

97073-15-9

SMILES

CC(N1CCCC1)C(C)=O

InChI Identifier

InChI=1S/C8H15NO/c1-7(8(2)10)9-5-3-4-6-9/h7H,3-6H2,1-2H3

InChI Key

IXYTUYCLJBLYKD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

N-alkylpyrrolidine
Alpha-aminoketone
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic oxygen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039840)
Cytoplasm (HMDB: HMDB0039840)

Source

Exogenous

Exogenous (HMDB: HMDB0039840)

Food

Food (HMDB: HMDB0039840)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039840)

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	113400 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	269 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.97	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.66 m³·mol⁻¹	ChemAxon
Polarizability	16.33 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]+	131.775	31661259
DarkChem	[M-H]-	127.051	31661259
DeepCCS	[M+H]+	132.458	30932474
DeepCCS	[M-H]-	130.259	30932474
DeepCCS	[M-2H]-	166.377	30932474
DeepCCS	[M+Na]+	141.187	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.7	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.4	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	136.7	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.	2.17 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7335 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.34 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	194.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	616.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	272.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	249.8 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	256.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	558.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	623.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.3 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	635.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	650.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	449.7 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	221.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(1-Pyrrolidinyl)-2-butanone	CC(N1CCCC1)C(C)=O	1360.1	Standard polar	33892256
3-(1-Pyrrolidinyl)-2-butanone	CC(N1CCCC1)C(C)=O	1058.5	Standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone	CC(N1CCCC1)C(C)=O	1059.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(1-Pyrrolidinyl)-2-butanone,1TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)N1CCCC1	1429.1	Semi standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)N1CCCC1	1316.9	Standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)N1CCCC1	1242.6	Semi standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)N1CCCC1	1259.4	Standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)N1CCCC1	1643.2	Semi standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)N1CCCC1	1504.6	Standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)N1CCCC1	1478.2	Semi standard non polar	33892256
3-(1-Pyrrolidinyl)-2-butanone,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)N1CCCC1	1435.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9000000000-9fa009d843b3d2fd359b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 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 - 3-(1-Pyrrolidinyl)-2-butanone 10V, Positive-QTOF	splash10-0006-1900000000-3afd47967f20b4aa22f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 20V, Positive-QTOF	splash10-00dm-7900000000-afe7f247d3e36cda92fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 40V, Positive-QTOF	splash10-05fu-9000000000-026efc7c725a5cba319a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-9a32874291d3e8738bea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 20V, Negative-QTOF	splash10-0006-6900000000-192b0a5d1a5b433da512	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 40V, Negative-QTOF	splash10-0600-9100000000-ce5c434f32c3dbac0de9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 10V, Positive-QTOF	splash10-0002-9100000000-54b8df6be96d76fafd58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 20V, Positive-QTOF	splash10-0002-9100000000-b63dab1914b13b1c6604	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 40V, Positive-QTOF	splash10-00ed-9000000000-ea56d95f1d39b646ffd2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 10V, Negative-QTOF	splash10-0006-4900000000-0977ef708ba6e14c44d0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 20V, Negative-QTOF	splash10-0006-9700000000-6ea6bd9ca2d6b950be74	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1-Pyrrolidinyl)-2-butanone 40V, Negative-QTOF	splash10-0006-9000000000-a29174ced6a5cdd6192d	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

FDB019494

KNApSAcK ID

Not Available

Chemspider ID

19092339

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23388489

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1880521

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 3-(1-Pyrrolidinyl)-2-butanone (HMDB0039840)

MOL for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

3D MOL for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

3D SDF for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

3D-SDF for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

PDB for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

3D PDB for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

SMILES for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

INCHI for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

Structure for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

3D Structure for HMDB0039840 (3-(1-Pyrrolidinyl)-2-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra