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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:58:36 UTC

Update Date

2023-02-21 17:29:56 UTC

HMDB ID

HMDB0060385

Secondary Accession Numbers

HMDB60385

Metabolite Identification

Common Name

4-Amino-1-piperidinecarboxylic acid

Description

4-Amino-1-piperidinecarboxylic acid belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group. 4-Amino-1-piperidinecarboxylic acid is a very strong basic compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Amino-1-piperidinecarboxylate	Generator

Chemical Formula

C₆H₁₂N₂O₂

Average Molecular Weight

144.1717

Monoisotopic Molecular Weight

144.089877638

IUPAC Name

4-aminopiperidine-1-carboxylic acid

Traditional Name

4-aminopiperidine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1CCN(CC1)C(O)=O

InChI Identifier

InChI=1S/C6H12N2O2/c7-5-1-3-8(4-2-5)6(9)10/h5H,1-4,7H2,(H,9,10)

InChI Key

NQNQKLBWDARKDG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxylic acids

Alternative Parents

Substituents

Piperidinecarboxylic acid
4-aminopiperidine
Carbamic acid
Carbamic acid derivative
Carbonic acid derivative
Azacycle
Amine
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

aminopiperidine (CHEBI:44262 )
piperidinemonocarboxylic acid (CHEBI:44262 )

Ontology

Not Available

Not Available

Not Available

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	549 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.2	ChemAxon
logS	0.58	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	9.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	36.5 m³·mol⁻¹	ChemAxon
Polarizability	14.77 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]+	131.83	31661259
DarkChem	[M-H]-	129.19	31661259
DeepCCS	[M+H]+	128.992	30932474
DeepCCS	[M-H]-	126.217	30932474
DeepCCS	[M-2H]-	162.768	30932474
DeepCCS	[M+Na]+	137.603	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	131.1	32859911
AllCCS	[M+HCOO]-	133.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-1-piperidinecarboxylic acid	NC1CCN(CC1)C(O)=O	2534.8	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid	NC1CCN(CC1)C(O)=O	1445.4	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid	NC1CCN(CC1)C(O)=O	1479.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-1-piperidinecarboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)N1CCC(N)CC1	1496.7	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,1TMS,isomer #2	C[Si](C)(C)NC1CCN(C(=O)O)CC1	1673.5	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #1	C[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C)CC1	1621.2	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #1	C[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C)CC1	1584.0	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #1	C[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C)CC1	2057.6	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #2	C[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C	1883.1	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #2	C[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C	1705.7	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TMS,isomer #2	C[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C	2357.1	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C)[Si](C)(C)C)CC1	1781.0	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C)[Si](C)(C)C)CC1	1747.1	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C)[Si](C)(C)C)CC1	1975.5	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)N1CCC(N)CC1	1747.0	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CCN(C(=O)O)CC1	1946.3	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C(C)(C)C)CC1	2060.5	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C(C)(C)C)CC1	2022.5	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCN(C(=O)O[Si](C)(C)C(C)(C)C)CC1	2215.8	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C(C)(C)C	2323.3	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C(C)(C)C	2164.9	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1CCN(C(=O)O)CC1)[Si](C)(C)C(C)(C)C	2397.2	Standard polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	2453.7	Semi standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	2417.2	Standard non polar	33892256
4-Amino-1-piperidinecarboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)N1CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	2266.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-1-piperidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9300000000-dd4387b764cb27d4afd8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-1-piperidinecarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05di-9210000000-c0abaddd94c6ebf71321	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 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 - 4-Amino-1-piperidinecarboxylic acid 10V, Positive-QTOF	splash10-0ufs-0900000000-83c9d60f56c4864eb6b8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 20V, Positive-QTOF	splash10-0ue9-4900000000-32840a6fbe0898f095d7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 40V, Positive-QTOF	splash10-05ai-9000000000-2fc0c7f419e1726de758	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 10V, Negative-QTOF	splash10-0007-6900000000-e289e9fa5ef494eba893	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 20V, Negative-QTOF	splash10-0005-8900000000-936c1a8cdcbfc413ee5d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 40V, Negative-QTOF	splash10-001j-9000000000-704848347783c461e145	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 10V, Positive-QTOF	splash10-002b-0900000000-f6a02cedbddd34013dbf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 20V, Positive-QTOF	splash10-0faj-8900000000-41bdce03d1309987171d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 40V, Positive-QTOF	splash10-05o0-9000000000-c9fb5c7f097fb216d790	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 10V, Negative-QTOF	splash10-0006-2900000000-ba3baf40c2fd378b620b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 20V, Negative-QTOF	splash10-01ox-9200000000-b9cf03ed6972f913559c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-1-piperidinecarboxylic acid 40V, Negative-QTOF	splash10-0006-9000000000-a06b03a4fe585b2a20f4	2021-10-12	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+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

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16837

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

445262

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

NPC + Water → SN-38 + 4-Amino-1-piperidinecarboxylic acid	details

Enzyme Details

2. Cocaine esterase

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:: CES2
Uniprot ID:: O00748
Molecular weight:: 68898.39

Reactions

NPC + Water → SN-38 + 4-Amino-1-piperidinecarboxylic acid	details

Showing metabocard for 4-Amino-1-piperidinecarboxylic acid (HMDB0060385)

MOL for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

3D MOL for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

3D SDF for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

3D-SDF for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

PDB for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

3D PDB for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

SMILES for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

INCHI for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

Structure for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

3D Structure for HMDB0060385 (4-Amino-1-piperidinecarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions