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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:35 UTC

Update Date

2023-02-21 17:21:05 UTC

HMDB ID

HMDB0031642

Secondary Accession Numbers

HMDB31642

Metabolite Identification

Common Name

N-Nitroso-pyrrolidine

Description

N-Nitroso-pyrrolidine belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. N-Nitroso-pyrrolidine has been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, pepper (c. annuum), red bell peppers, and yellow bell peppers. This could make N-nitroso-pyrrolidine a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Nitrosopyrrolidine	MeSH
N Nitrosopyrrolidine	MeSH
1-Nitrosopyrrolidine	ChEMBL, HMDB
1-nitroso-Pyrrolidine	ChEMBL, HMDB
N-nitroso-1-Pyrrolidinamine	HMDB
nitroso-Pyrrolidine	HMDB
Nitrosopyrrolidine	HMDB
tetrahydro-N-nitroso-Pyrrole	HMDB

Chemical Formula

C₄H₈N₂O

Average Molecular Weight

100.1191

Monoisotopic Molecular Weight

100.063662888

IUPAC Name

1-nitrosopyrrolidine

Traditional Name

N-nitrosopyrrolidine

CAS Registry Number

930-55-2

SMILES

O=NN1CCCC1

InChI Identifier

InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2

InChI Key

WNYADZVDBIBLJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which 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

Not Available

Direct Parent

Pyrrolidines

Alternative Parents

Substituents

Pyrrolidine
Organic n-nitroso compound
Organic nitroso compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidines (CHEBI:82362 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031642)
Cytoplasm (HMDB: HMDB0031642)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031642)

Source

Endogenous

Endogenous (HMDB: HMDB0031642)

Plant

Plant (HMDB: HMDB0031642)

Exogenous

Food

Food (HMDB: HMDB0031642)

Vegetable

Fruit vegetable

Environmental

Wastewater (HMDB: HMDB0031642)
Tobacco Smoke (HMDB: HMDB0031642)

Exogenous (HMDB: HMDB0031642)

Process

Industrial process

Disinfection

Water Disinfection (HMDB: HMDB0031642)

Role

Environmental role

Air pollutant (HMDB: HMDB0031642)

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	1000000 mg/L @ 24C (exp)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	52.9 g/L	ALOGPS
logP	-0.07	ALOGPS
logP	0.44	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Basic)	3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.59 m³·mol⁻¹	ChemAxon
Polarizability	10.02 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]+	119.344	31661259
DarkChem	[M-H]-	112.989	31661259
DeepCCS	[M+H]+	125.488	30932474
DeepCCS	[M-H]-	123.34	30932474
DeepCCS	[M-2H]-	158.819	30932474
DeepCCS	[M+Na]+	133.475	30932474
AllCCS	[M+H]+	121.1	32859911
AllCCS	[M+H-H2O]+	116.1	32859911
AllCCS	[M+NH4]+	125.7	32859911
AllCCS	[M+Na]+	127.0	32859911
AllCCS	[M-H]-	120.7	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	127.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitroso-pyrrolidine	O=NN1CCCC1	1678.8	Standard polar	33892256
N-Nitroso-pyrrolidine	O=NN1CCCC1	916.3	Standard non polar	33892256
N-Nitroso-pyrrolidine	O=NN1CCCC1	1079.9	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-Nitroso-pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g2c-9000000000-25d8797fa4ff751a2d70	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitroso-pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6x-9300000000-c9950fc76ef0705da573	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0udi-1900000000-85f43e28b348aeb93404	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0udi-1900000000-85f43e28b348aeb93404	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0udi-1900000000-85f43e28b348aeb93404	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0udi-3900000000-79fa9d8de9566bec999e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0zfr-7900000000-0a674ea8d4b2d3f65b02	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF	splash10-0pb9-9500000000-98bb6cb1fe4c3f9a5bc7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 30V, Positive-QTOF	splash10-0udi-1900000000-84056e4af9b3004d1162	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 75V, Positive-QTOF	splash10-0zfr-7900000000-fda6e8cba67fb1021878	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 90V, Positive-QTOF	splash10-0pb9-9500000000-84c6d034657142a09d21	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 60V, Positive-QTOF	splash10-0udi-3900000000-e01767039cac569f296c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Negative-QTOF	splash10-0002-9000000000-4f72e350127fc271c203	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Negative-QTOF	splash10-001j-9000000000-370f605a1fa54cb29bff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Negative-QTOF	splash10-0aor-9000000000-e5d77a59e81129df0a5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Negative-QTOF	splash10-0002-9000000000-0b57691aff180313e37a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Negative-QTOF	splash10-0002-9000000000-67edf338cfba7b6ef1e3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Negative-QTOF	splash10-00kb-9000000000-4c1cf43c5f1ce342a8ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Positive-QTOF	splash10-0udi-2900000000-954c68340e2ec5c96773	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Positive-QTOF	splash10-0uk9-9400000000-b485c8519f27b43bd31e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Positive-QTOF	splash10-006x-9000000000-c7530b5d976c4a448753	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Positive-QTOF	splash10-0udi-3900000000-9fcafc467833636e9b20	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Positive-QTOF	splash10-0uk9-9600000000-6331dff30f7d5884aa62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Positive-QTOF	splash10-0abc-9000000000-080a502c75e912983699	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008291

KNApSAcK ID

Not Available

Chemspider ID

13002

KEGG Compound ID

C19285

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13591

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1155851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tatematsu K, Koide A, Morimura K, Fukushima S, Mori Y: The enhancing effect of ethanol on the mutagenic activation of N-nitrosomethylbenzylamine by cytochrome P450 2A in the rat oesophagus. Mutagenesis. 2013 Mar;28(2):161-9. doi: 10.1093/mutage/ges066. Epub 2013 Jan 15. [PubMed:23325793 ]
Li L, Wang P, Xu X, Zhou G: Influence of various cooking methods on the concentrations of volatile N-nitrosamines and biogenic amines in dry-cured sausages. J Food Sci. 2012 May;77(5):C560-5. doi: 10.1111/j.1750-3841.2012.02667.x. [PubMed:23163937 ]
Pozzi R, Bocchini P, Pinelli F, Galletti GC: Determination of nitrosamines in water by gas chromatography/chemical ionization/selective ion trapping mass spectrometry. J Chromatogr A. 2011 Apr 8;1218(14):1808-14. doi: 10.1016/j.chroma.2011.02.009. Epub 2011 Feb 13. [PubMed:21377686 ]
Authors unspecified: N-Nitrosamines (15 listings): N-Nitrosopyrrolidine. Rep Carcinog. 2011;12:323-4. [PubMed:21860516 ]
Wagner ED, Hsu KM, Lagunas A, Mitch WA, Plewa MJ: Comparative genotoxicity of nitrosamine drinking water disinfection byproducts in Salmonella and mammalian cells. Mutat Res. 2012 Jan 24;741(1-2):109-15. doi: 10.1016/j.mrgentox.2011.11.006. Epub 2011 Nov 18. [PubMed:22108029 ]
Hecht SS, Upadhyaya P, Wang M: Evolution of research on the DNA adduct chemistry of N-nitrosopyrrolidine and related aldehydes. Chem Res Toxicol. 2011 Jun 20;24(6):781-90. doi: 10.1021/tx200064a. Epub 2011 Apr 21. [PubMed:21480629 ]
Tezel U, Padhye LP, Huang CH, Pavlostathis SG: Biotransformation of nitrosamines and precursor secondary amines under methanogenic conditions. Environ Sci Technol. 2011 Oct 1;45(19):8290-7. doi: 10.1021/es2005557. Epub 2011 Sep 2. [PubMed:21863807 ]
Ma F, Wan Y, Yuan G, Meng L, Dong Z, Hu J: Occurrence and source of nitrosamines and secondary amines in groundwater and its adjacent Jialu River basin, China. Environ Sci Technol. 2012 Mar 20;46(6):3236-43. doi: 10.1021/es204520b. Epub 2012 Mar 1. [PubMed:22352424 ]
Engemann A, Focke C, Humpf HU: Intestinal formation of N-nitroso compounds in the pig cecum model. J Agric Food Chem. 2013 Jan 30;61(4):998-1005. doi: 10.1021/jf305040e. Epub 2013 Jan 22. [PubMed:23297847 ]
McDonald JA, Harden NB, Nghiem LD, Khan SJ: Analysis of N-nitrosamines in water by isotope dilution gas chromatography-electron ionisation tandem mass spectrometry. Talanta. 2012 Sep 15;99:146-54. doi: 10.1016/j.talanta.2012.05.032. Epub 2012 May 25. [PubMed:22967534 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-Nitroso-pyrrolidine (HMDB0031642)

MOL for HMDB0031642 (N-Nitroso-pyrrolidine)

3D MOL for HMDB0031642 (N-Nitroso-pyrrolidine)

3D SDF for HMDB0031642 (N-Nitroso-pyrrolidine)

3D-SDF for HMDB0031642 (N-Nitroso-pyrrolidine)

PDB for HMDB0031642 (N-Nitroso-pyrrolidine)

3D PDB for HMDB0031642 (N-Nitroso-pyrrolidine)

SMILES for HMDB0031642 (N-Nitroso-pyrrolidine)

INCHI for HMDB0031642 (N-Nitroso-pyrrolidine)

Structure for HMDB0031642 (N-Nitroso-pyrrolidine)

3D Structure for HMDB0031642 (N-Nitroso-pyrrolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra