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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:05:40 UTC

Update Date

2021-09-26 22:51:12 UTC

HMDB ID

HMDB0243873

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Ethyl-1-nitrosourea

Description

N-ethyl-N-nitrosourea, also known as aethylnitroso-harnstoff or ENU, belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O. Based on a literature review a significant number of articles have been published on N-ethyl-N-nitrosourea. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-ethyl-1-nitrosourea is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Ethyl-1-nitrosourea is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

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-(Aminocarbonyl)-1-ethyl-2-oxohydrazine	ChEBI
1-Ethyl-1-nitrosourea	ChEBI
Aethylnitroso-harnstoff	ChEBI
ENU	ChEBI
Ethyl nitrosourea	ChEBI
N-Ethyl-N-nitroso carbamide	ChEBI
N-Ethyl-N-nitroso-urea	ChEBI
N-Ethylnitrosourea	ChEBI
NEU	ChEBI
Nitrosoethylurea	MeSH
Ethylnitrosourea	MeSH
N Ethyl N nitrosourea	MeSH
N-Ethyl-N-nitrosourea	MeSH

Chemical Formula

C₃H₇N₃O₂

Average Molecular Weight

117.108

Monoisotopic Molecular Weight

117.053826477

IUPAC Name

N-(C-hydroxycarbonimidoyl)-N-nitrosoethan-1-amine

Traditional Name

ENU

CAS Registry Number

Not Available

SMILES

CCN(N=O)C(O)=N

InChI Identifier

InChI=1S/C3H7N3O2/c1-2-6(5-8)3(4)7/h2H2,1H3,(H2,4,7)

InChI Key

FUSGACRLAFQQRL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Nitrosoureas

Alternative Parents

Substituents

Nitrosourea
Nitrosamide
Semicarbazide
Organic n-nitroso compound
Organic nitroso compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-nitrosoureas (CHEBI:23995 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	-0.17	ALOGPS
logP	0.65	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	1.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.75 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.08 m³·mol⁻¹	ChemAxon
Polarizability	10.31 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	124.711	30932474
DeepCCS	[M-H]-	122.778	30932474
DeepCCS	[M-2H]-	158.909	30932474
DeepCCS	[M+Na]+	133.467	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	125.4	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	123.1	32859911
AllCCS	[M+Na-2H]-	126.5	32859911
AllCCS	[M+HCOO]-	130.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Ethyl-1-nitrosourea	CCN(N=O)C(O)=N	1732.6	Standard polar	33892256
1-Ethyl-1-nitrosourea	CCN(N=O)C(O)=N	1284.4	Standard non polar	33892256
1-Ethyl-1-nitrosourea	CCN(N=O)C(O)=N	1256.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Ethyl-1-nitrosourea,2TMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C)O[Si](C)(C)C	1417.9	Semi standard non polar	33892256
1-Ethyl-1-nitrosourea,2TMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C)O[Si](C)(C)C	1294.2	Standard non polar	33892256
1-Ethyl-1-nitrosourea,2TMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C)O[Si](C)(C)C	2083.1	Standard polar	33892256
1-Ethyl-1-nitrosourea,2TBDMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1770.0	Semi standard non polar	33892256
1-Ethyl-1-nitrosourea,2TBDMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1671.2	Standard non polar	33892256
1-Ethyl-1-nitrosourea,2TBDMS,isomer #1	CCN(N=O)C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2118.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-5894a08b09825ee28203	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethyl-1-nitrosourea GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 1-Ethyl-1-nitrosourea 10V, Positive-QTOF	splash10-016r-8900000000-7a3bb09f39708aa56472	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 20V, Positive-QTOF	splash10-004l-9000000000-442f65cfa368746c8352	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 40V, Positive-QTOF	splash10-0006-9000000000-14ee51ad0113d3a41b7a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 10V, Negative-QTOF	splash10-006x-9000000000-83709128dbbebe87c15a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 20V, Negative-QTOF	splash10-00dm-9000000000-3116cac77a71e3668290	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 40V, Negative-QTOF	splash10-0006-9000000000-282a6b7701e3aae4cbdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 10V, Positive-QTOF	splash10-004l-9100000000-f64e76293104477cca0d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 20V, Positive-QTOF	splash10-0a6u-9000000000-619531d12a4f11b524f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 40V, Positive-QTOF	splash10-00dl-9000000000-f75bc613083d202a1e6d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 10V, Negative-QTOF	splash10-0006-9100000000-054042ce773d32609ba4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 20V, Negative-QTOF	splash10-0006-9000000000-2d577c042b599601912d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethyl-1-nitrosourea 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	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)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

12427

KEGG Compound ID

C19178

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

ENU

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

23995

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1-Ethyl-1-nitrosourea (HMDB0243873)

MOL for HMDB0243873 (1-Ethyl-1-nitrosourea)

3D MOL for HMDB0243873 (1-Ethyl-1-nitrosourea)

3D SDF for HMDB0243873 (1-Ethyl-1-nitrosourea)

3D-SDF for HMDB0243873 (1-Ethyl-1-nitrosourea)

PDB for HMDB0243873 (1-Ethyl-1-nitrosourea)

3D PDB for HMDB0243873 (1-Ethyl-1-nitrosourea)

SMILES for HMDB0243873 (1-Ethyl-1-nitrosourea)

INCHI for HMDB0243873 (1-Ethyl-1-nitrosourea)

Structure for HMDB0243873 (1-Ethyl-1-nitrosourea)

3D Structure for HMDB0243873 (1-Ethyl-1-nitrosourea)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra