Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:21 UTC

Update Date

2023-02-21 17:29:04 UTC

HMDB ID

HMDB0041946

Secondary Accession Numbers

HMDB41946

Metabolite Identification

Common Name

N-Nitrosoproline

Description

N-Nitrosoproline, also known as NO-pro, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Nitrosoproline 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 N-nitrosoproline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Nitrosoproline.

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-Nitroso-L-proline	HMDB
1-Nitrosoproline (acd/name 4.0)	HMDB
N-Nitroso-L-proline	HMDB
Nitroso-L-proline	HMDB
Nitrosoproline	HMDB
NO-Pro	HMDB
NPRO	HMDB
Nitrosoproline, (cis)-isomer	HMDB
Nitrosoproline, (trans)-isomer	HMDB
Nitrosoproline, 14C-labeled CPD	HMDB
Nitrosoproline, (D,L)-isomer	HMDB
Nitrosoproline, (D)-isomer	HMDB
1-Nitrosopyrrolidine-2-carboxylate	HMDB
N-Nitrosoproline	MeSH

Chemical Formula

C₅H₈N₂O₃

Average Molecular Weight

144.1286

Monoisotopic Molecular Weight

144.053492132

IUPAC Name

1-nitrosopyrrolidine-2-carboxylic acid

Traditional Name

nitrosoproline

CAS Registry Number

7519-36-0

SMILES

OC(=O)C1CCCN1N=O

InChI Identifier

InChI=1S/C5H8N2O3/c8-5(9)4-2-1-3-7(4)6-10/h4H,1-3H2,(H,8,9)

InChI Key

WLKPHJWEIIAIFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Organic n-nitroso compound
Organic nitroso compound
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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

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	43.1 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	0.013	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	2.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.42 m³·mol⁻¹	ChemAxon
Polarizability	12.92 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]+	130.271	31661259
DarkChem	[M-H]-	125.521	31661259
DeepCCS	[M+H]+	125.646	30932474
DeepCCS	[M-H]-	123.407	30932474
DeepCCS	[M-2H]-	159.647	30932474
DeepCCS	[M+Na]+	134.43	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	125.8	32859911
AllCCS	[M+Na-2H]-	127.5	32859911
AllCCS	[M+HCOO]-	129.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosoproline	OC(=O)C1CCCN1N=O	2101.5	Standard polar	33892256
N-Nitrosoproline	OC(=O)C1CCCN1N=O	1401.5	Standard non polar	33892256
N-Nitrosoproline	OC(=O)C1CCCN1N=O	1544.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosoproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCCN1N=O	1502.5	Semi standard non polar	33892256
N-Nitrosoproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1N=O	1758.5	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 - N-Nitrosoproline GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9100000000-4c76df1934b69fd8cee4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosoproline GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9200000000-8d02dc80048c159067cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosoproline 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 - N-Nitrosoproline 10V, Positive-QTOF	splash10-0002-1900000000-88da6af2dfad7ef72d20	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Positive-QTOF	splash10-0002-5900000000-e3af96f067eaf91cdba9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Positive-QTOF	splash10-0006-9000000000-5783b4e9c7f80712ef65	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Negative-QTOF	splash10-0007-5900000000-cd35a3d360022913a561	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Negative-QTOF	splash10-002b-9400000000-19d3f92911b61a661505	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Negative-QTOF	splash10-0aor-9100000000-ff5802d4b6e78532625b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Negative-QTOF	splash10-0006-2900000000-5af2e2f6d4ae9ed5123b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Negative-QTOF	splash10-014j-9100000000-aa63d528a3a61240fea9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Negative-QTOF	splash10-0002-9000000000-0a69d5519333a983f48d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Positive-QTOF	splash10-002b-8900000000-d143893f34ed790c2c2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Positive-QTOF	splash10-0002-9300000000-d7a035b4e5efd70d97b3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Positive-QTOF	splash10-0a4i-9000000000-4b5ecbdedb2bdc511c55	2021-09-25	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

FDB111682

KNApSAcK ID

Not Available

Chemspider ID

22565

KEGG Compound ID

C19485

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitrosoproline

METLIN ID

Not Available

PubChem Compound

24141

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

Not Available

Showing metabocard for N-Nitrosoproline (HMDB0041946)

MOL for HMDB0041946 (N-Nitrosoproline)

3D MOL for HMDB0041946 (N-Nitrosoproline)

3D SDF for HMDB0041946 (N-Nitrosoproline)

3D-SDF for HMDB0041946 (N-Nitrosoproline)

PDB for HMDB0041946 (N-Nitrosoproline)

3D PDB for HMDB0041946 (N-Nitrosoproline)

SMILES for HMDB0041946 (N-Nitrosoproline)

INCHI for HMDB0041946 (N-Nitrosoproline)

Structure for HMDB0041946 (N-Nitrosoproline)

3D Structure for HMDB0041946 (N-Nitrosoproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra