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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:51:53 UTC

Update Date

2023-02-21 17:30:21 UTC

HMDB ID

HMDB0061163

Secondary Accession Numbers

HMDB61163

Metabolite Identification

Common Name

N-Nitroso-3-hydroxypyrrolidine

Description

N-Nitroso-3-hydroxypyrrolidine is a metabolite of piperazine. Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group. (Wikipedia)

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-1-nitrosopyrrolidine	HMDB
N-nitroso-3-Hydroxypyrrolidine	MeSH

Chemical Formula

C₄H₈N₂O₂

Average Molecular Weight

116.1185

Monoisotopic Molecular Weight

116.05857751

IUPAC Name

1-nitrosopyrrolidin-3-ol

Traditional Name

1-nitrosopyrrolidin-3-ol

CAS Registry Number

Not Available

SMILES

OC1CCN(C1)N=O

InChI Identifier

InChI=1S/C4H8N2O2/c7-4-1-2-6(3-4)5-8/h4,7H,1-3H2

InChI Key

XDZKGLWJXJTZJZ-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
Secondary alcohol
Organic nitroso compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0061163)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061163)

Organ

Liver (HMDB: HMDB0061163)
Kidney (HMDB: HMDB0061163)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061163)

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	137 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.7	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	3.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.91 m³·mol⁻¹	ChemAxon
Polarizability	10.91 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]+	122.815	31661259
DarkChem	[M-H]-	116.521	31661259
DeepCCS	[M+H]+	124.951	30932474
DeepCCS	[M-H]-	122.939	30932474
DeepCCS	[M-2H]-	158.76	30932474
DeepCCS	[M+Na]+	133.215	30932474
AllCCS	[M+H]+	125.5	32859911
AllCCS	[M+H-H2O]+	120.7	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.2	32859911
AllCCS	[M-H]-	122.2	32859911
AllCCS	[M+Na-2H]-	124.8	32859911
AllCCS	[M+HCOO]-	127.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitroso-3-hydroxypyrrolidine	OC1CCN(C1)N=O	2059.1	Standard polar	33892256
N-Nitroso-3-hydroxypyrrolidine	OC1CCN(C1)N=O	1119.5	Standard non polar	33892256
N-Nitroso-3-hydroxypyrrolidine	OC1CCN(C1)N=O	1352.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Nitroso-3-hydroxypyrrolidine,1TMS,isomer #1	C[Si](C)(C)OC1CCN(N=O)C1	1386.9	Semi standard non polar	33892256
N-Nitroso-3-hydroxypyrrolidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCN(N=O)C1	1620.6	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-3-hydroxypyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-c49a27eb98605985822f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitroso-3-hydroxypyrrolidine GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9700000000-b8bb6d7f9811e7f230c4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 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-Nitroso-3-hydroxypyrrolidine 10V, Positive-QTOF	splash10-0002-9200000000-08e527b83ac01a23616e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 20V, Positive-QTOF	splash10-0002-9000000000-0a749573b0435e0988d6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 40V, Positive-QTOF	splash10-014l-9000000000-71b6ec51e247e14444a3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 10V, Negative-QTOF	splash10-014i-4900000000-ea4adc6e9a90e6f7d951	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 20V, Negative-QTOF	splash10-0002-9200000000-86746d55d8e8abb8f87f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 40V, Negative-QTOF	splash10-0a4i-9000000000-ae6f53e6a79314a78ef4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 10V, Negative-QTOF	splash10-014i-7900000000-e0f85c8b5776f21b78e1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 20V, Negative-QTOF	splash10-0002-9100000000-cd295a4771ac30a6beac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 40V, Negative-QTOF	splash10-0006-9000000000-93b9e9485f622da6a399	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 10V, Positive-QTOF	splash10-014i-3900000000-6079d685353b20b561de	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 20V, Positive-QTOF	splash10-01ba-9400000000-dd867f412046abd49e20	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitroso-3-hydroxypyrrolidine 40V, Positive-QTOF	splash10-0a4m-9000000000-0b125d39e40c73a3428f	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

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3034827

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-Nitroso-3-hydroxypyrrolidine (HMDB0061163)

MOL for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

3D MOL for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

3D SDF for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

3D-SDF for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

PDB for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

3D PDB for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

SMILES for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

INCHI for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

Structure for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

3D Structure for HMDB0061163 (N-Nitroso-3-hydroxypyrrolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra