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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:42 UTC

HMDB ID

HMDB0000323

Secondary Accession Numbers

HMDB00323

Metabolite Identification

Common Name

3-Amino-2-piperidone

Description

3-Amino-2-piperidone, also known as cyclo-ornithine or 3-aminopiperidine-2-one, belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 3-Amino-2-piperidone exists in all living organisms, ranging from bacteria to humans. 3-Amino-2-piperidone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-amino-2-piperidone a potential biomarker for the consumption of these foods. 3-Amino-2-piperidone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 3-Amino-2-piperidone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cyclo-ornithine	ChEBI
(+)-3-Aminopiperidin-2-one	HMDB
(R)-(+)-3-Amino-2-piperidinon	HMDB
(S)-(-)-3-Amino-2-piperidinon	HMDB
(S)-3-Amino-2-piperidinon	HMDB
3-Amino-2-piperidinone	HMDB
Ornithine N5-lactam	HMDB
3-Aminopiperidine-2-one	HMDB
3-Amino-2-piperidone	ChEBI

Chemical Formula

C₅H₁₀N₂O

Average Molecular Weight

114.1457

Monoisotopic Molecular Weight

114.079312952

IUPAC Name

3-aminopiperidin-2-one

Traditional Name

3-amino-2-piperidone

CAS Registry Number

1892-22-4

SMILES

NC1CCCNC1=O

InChI Identifier

InChI=1S/C5H10N2O/c6-4-2-1-3-7-5(4)8/h4H,1-3,6H2,(H,7,8)

InChI Key

YCCMTCQQDULIFE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
3-aminopiperidine
Delta-lactam
Piperidinone
Piperidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Primary amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

primary amino compound (CHEBI:76341 )
delta-lactam (CHEBI:76341 )
piperidones (CHEBI:76341 )

Ontology

Not Available

Sweat (HMDB: HMDB0000323)

Source

Endogenous

Endogenous (HMDB: HMDB0000323)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	444 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.1	ChemAxon
logS	0.59	ALOGPS
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	8.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.01 m³·mol⁻¹	ChemAxon
Polarizability	11.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.982	31661259
DarkChem	[M-H]-	116.673	31661259
AllCCS	[M+H]+	123.746	32859911
AllCCS	[M-H]-	119.416	32859911
DeepCCS	[M+H]+	135.268	30932474
DeepCCS	[M-H]-	132.508	30932474
DeepCCS	[M-2H]-	168.772	30932474
DeepCCS	[M+Na]+	143.523	30932474
AllCCS	[M+H]+	123.7	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	128.3	32859911
AllCCS	[M+Na]+	129.7	32859911
AllCCS	[M-H]-	119.4	32859911
AllCCS	[M+Na-2H]-	121.9	32859911
AllCCS	[M+HCOO]-	124.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-2-piperidone	NC1CCCNC1=O	2110.9	Standard polar	33892256
3-Amino-2-piperidone	NC1CCCNC1=O	1143.5	Standard non polar	33892256
3-Amino-2-piperidone	NC1CCCNC1=O	1309.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-2-piperidone,1TMS,isomer #1	C[Si](C)(C)NC1CCCNC1=O	1394.6	Semi standard non polar	33892256
3-Amino-2-piperidone,1TMS,isomer #1	C[Si](C)(C)NC1CCCNC1=O	1266.5	Standard non polar	33892256
3-Amino-2-piperidone,1TMS,isomer #1	C[Si](C)(C)NC1CCCNC1=O	2328.9	Standard polar	33892256
3-Amino-2-piperidone,1TMS,isomer #2	C[Si](C)(C)N1CCCC(N)C1=O	1317.0	Semi standard non polar	33892256
3-Amino-2-piperidone,1TMS,isomer #2	C[Si](C)(C)N1CCCC(N)C1=O	1214.9	Standard non polar	33892256
3-Amino-2-piperidone,1TMS,isomer #2	C[Si](C)(C)N1CCCC(N)C1=O	2224.5	Standard polar	33892256
3-Amino-2-piperidone,2TMS,isomer #1	C[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C	1517.2	Semi standard non polar	33892256
3-Amino-2-piperidone,2TMS,isomer #1	C[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C	1524.1	Standard non polar	33892256
3-Amino-2-piperidone,2TMS,isomer #1	C[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C	2146.5	Standard polar	33892256
3-Amino-2-piperidone,2TMS,isomer #2	C[Si](C)(C)NC1CCCN([Si](C)(C)C)C1=O	1445.5	Semi standard non polar	33892256
3-Amino-2-piperidone,2TMS,isomer #2	C[Si](C)(C)NC1CCCN([Si](C)(C)C)C1=O	1428.4	Standard non polar	33892256
3-Amino-2-piperidone,2TMS,isomer #2	C[Si](C)(C)NC1CCCN([Si](C)(C)C)C1=O	1983.2	Standard polar	33892256
3-Amino-2-piperidone,3TMS,isomer #1	C[Si](C)(C)N1CCCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1541.1	Semi standard non polar	33892256
3-Amino-2-piperidone,3TMS,isomer #1	C[Si](C)(C)N1CCCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1657.0	Standard non polar	33892256
3-Amino-2-piperidone,3TMS,isomer #1	C[Si](C)(C)N1CCCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1777.7	Standard polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCNC1=O	1643.0	Semi standard non polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCNC1=O	1538.8	Standard non polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCNC1=O	2489.7	Standard polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCC(N)C1=O	1547.6	Semi standard non polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCC(N)C1=O	1474.1	Standard non polar	33892256
3-Amino-2-piperidone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCC(N)C1=O	2438.3	Standard polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C(C)(C)C	1955.6	Semi standard non polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C(C)(C)C	1976.6	Standard non polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCNC1=O)[Si](C)(C)C(C)(C)C	2201.8	Standard polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CCCN([Si](C)(C)C(C)(C)C)C1=O	1876.3	Semi standard non polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CCCN([Si](C)(C)C(C)(C)C)C1=O	1932.7	Standard non polar	33892256
3-Amino-2-piperidone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CCCN([Si](C)(C)C(C)(C)C)C1=O	2130.8	Standard polar	33892256
3-Amino-2-piperidone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	2218.1	Semi standard non polar	33892256
3-Amino-2-piperidone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	2351.8	Standard non polar	33892256
3-Amino-2-piperidone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	2109.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Amino-2-piperidone GC-MS (2 TMS)	splash10-00ou-1910000000-92400ccbe60c08f72840	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Amino-2-piperidone GC-MS (Non-derivatized)	splash10-00ou-1910000000-92400ccbe60c08f72840	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-2-piperidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-4f67e2bb33f23a8162d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-2-piperidone 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-Amino-2-piperidone 10V, Positive-QTOF	splash10-014i-3900000000-b8721f62b29b4da04620	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 20V, Positive-QTOF	splash10-014i-9700000000-665ba82e0b94c5b287d7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 40V, Positive-QTOF	splash10-0006-9000000000-440cca1df99eb06f21c7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 10V, Negative-QTOF	splash10-03di-3900000000-a8f9a049f9d1147c87ed	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 20V, Negative-QTOF	splash10-03di-9600000000-4554d3f81d3e188ef0da	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 40V, Negative-QTOF	splash10-052f-9000000000-378339ec915807272f53	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 10V, Negative-QTOF	splash10-03di-0900000000-4eb8c76fed602ca148ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 20V, Negative-QTOF	splash10-03di-5900000000-cda9a3adcb344e3fdb2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 40V, Negative-QTOF	splash10-0006-9000000000-9718e3ed51aaf3bc990a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 10V, Positive-QTOF	splash10-014i-1900000000-3231d43c7c0668858742	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 20V, Positive-QTOF	splash10-0601-9200000000-5b02fb65d9fb82bc034e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-2-piperidone 40V, Positive-QTOF	splash10-0a4i-9000000000-fe451a154df71739dbe2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Sweat

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details

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

FDB021949

KNApSAcK ID

C00052808

Chemspider ID

4371576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5312

PubChem Compound

5200225

PDB ID

Not Available

ChEBI ID

76341

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Moon, Byong Hoon; Martin, Charles Franklin. 3-Aminopiperidones. V. 2-Ethoxy and 2-carbethoxy derivatives of 2-p-methoxyphenylglutarimide. Journal of Pharmaceutical Sciences (1971), 60(4), 618-20.

Material Safety Data Sheet (MSDS)

Not Available

General References

Oberholzer VG, Briddon A: 3-Amino-2-piperidone in the urine of patients with hyperornithinemia. Clin Chim Acta. 1978 Aug 1;87(3):411-5. [PubMed:679477 ]
Arshinoff SA, McCulloch JC, Matuk Y, Phillips MJ, Gordon BA, Marliss EB: Amino-acid metabolism and liver ultrastructure in hyperornithinemia with gyrate atrophy of the choroid and retina. Metabolism. 1979 Oct;28(10):979-88. [PubMed:491962 ]

Showing metabocard for 3-Amino-2-piperidone (HMDB0000323)

MOL for HMDB0000323 (3-Amino-2-piperidone)

3D MOL for HMDB0000323 (3-Amino-2-piperidone)

3D SDF for HMDB0000323 (3-Amino-2-piperidone)

3D-SDF for HMDB0000323 (3-Amino-2-piperidone)

PDB for HMDB0000323 (3-Amino-2-piperidone)

3D PDB for HMDB0000323 (3-Amino-2-piperidone)

SMILES for HMDB0000323 (3-Amino-2-piperidone)

INCHI for HMDB0000323 (3-Amino-2-piperidone)

Structure for HMDB0000323 (3-Amino-2-piperidone)

3D Structure for HMDB0000323 (3-Amino-2-piperidone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra