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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:47:02 UTC

Update Date

2021-09-26 23:09:49 UTC

HMDB ID

HMDB0255205

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Nitrosodipropylamine

Description

n-Nitrosodi-n-propylamine belongs to the class of organic compounds known as organic n-nitroso compounds. These are organic compounds containing a n-nitroso group -NN=O. n-Nitrosodi-n-propylamine is a strong basic compound (based on its pKa). n-Nitrosodi-n-propylamine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. N-Nitrosodi-n-propylamine is a chemical produced by industry in small amounts for research. Small amounts of n-nitrosodi-n-propylamine are also produced as a side reaction during some manufacturing processes, as a contaminant in some weed killers, and during the manufacture of some rubber products. The metabolites of n-nitrosodi-n-propylamine are excreted mainly in the urine. High levels of n-nitrosodi-n-propylamine may damage the liver, lung, stomach, kidneys, and heart. n-Nitrosodi-n-propylamine is also a likely carcinogen. Alpha carbon oxidation is regarded as the primary pathway, resulting in formation of propionaldehyde, 1-propanol, and 2-propanol. Reactive metabolites of n-nitrosodi-n-propylamine are believed to form adducts with DNA, resulting in carcinogenic effects. It is metabolized by cytochrome p-450 enzymes (mainly CYP 2E1) into its reactive metabolites via oxidation at the alpha, beta and gamma carbon positions. It is one ingredient of cigarette. n-Nitrosodi-n-propylamine can be absorbed through oral, inhalation, or dermal routes. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-nitrosodipropylamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Nitrosodipropylamine 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
N,N-Dipropylnitrosamine	MeSH
N-nitroso(Di-N-propyl)amine	MeSH
Dipropylnitrosamine	MeSH

Chemical Formula

C₆H₁₄N₂O

Average Molecular Weight

130.1882

Monoisotopic Molecular Weight

130.11061308

IUPAC Name

nitrosodipropylamine

Traditional Name

N-nitrosodipropylamine

CAS Registry Number

Not Available

SMILES

CCCN(CCC)N=O

InChI Identifier

InChI=1S/C6H14N2O/c1-3-5-8(7-9)6-4-2/h3-6H2,1-2H3

InChI Key

YLKFDHTUAUWZPQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic n-nitroso compounds. These are organic compounds containing a n-nitroso group -NN=O.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Organic nitroso compounds

Direct Parent

Organic N-nitroso compounds

Alternative Parents

Substituents

Organic n-nitroso compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nitroso compound (CHEBI:82358 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	1.57	ALOGPS
logP	1.8	ChemAxon
logS	-0.93	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	5	ChemAxon
Refractivity	38.6 m³·mol⁻¹	ChemAxon
Polarizability	15.02 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	131.942	30932474
DeepCCS	[M-H]-	129.625	30932474
DeepCCS	[M-2H]-	165.768	30932474
DeepCCS	[M+Na]+	140.575	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	136.4	32859911
AllCCS	[M+Na]+	137.5	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	134.8	32859911
AllCCS	[M+HCOO]-	138.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosodipropylamine	CCCN(CCC)N=O	1467.4	Standard polar	33892256
N-Nitrosodipropylamine	CCCN(CCC)N=O	920.8	Standard non polar	33892256
N-Nitrosodipropylamine	CCCN(CCC)N=O	1072.8	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-Nitrosodipropylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9200000000-7a59226c684fdfa7f3f4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosodipropylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-632355cddcea307ac9e7	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-Nitrosodipropylamine 30V, Positive-QTOF	splash10-0019-9500000000-0704dc1a231c669f02cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodipropylamine 45V, Positive-QTOF	splash10-000i-9200000000-154023f596f82ff60612	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodipropylamine 75V, Positive-QTOF	splash10-0udr-9000000000-cf38c049fad6b029abf9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodipropylamine 60V, Positive-QTOF	splash10-000i-9000000000-7f3e7dfc90998dac6805	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodipropylamine 90V, Positive-QTOF	splash10-0udi-9000000000-7817e43d165c2c3db63a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 10V, Positive-QTOF	splash10-001i-3900000000-519b13d74f5fd41dae33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 20V, Positive-QTOF	splash10-0006-9200000000-ec2e51e590dd7bb0651d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 40V, Positive-QTOF	splash10-0006-9000000000-b184a59d7647d7a9126a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 10V, Negative-QTOF	splash10-004i-1900000000-de2892f0b560af379291	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 20V, Negative-QTOF	splash10-01t9-4900000000-24bf802b1bb215f4745f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodipropylamine 40V, Negative-QTOF	splash10-0006-9000000000-d063bf39130b38e25ac9	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

Not Available

KEGG Compound ID

C19279

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

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 N-Nitrosodipropylamine (HMDB0255205)

MOL for HMDB0255205 (N-Nitrosodipropylamine)

3D MOL for HMDB0255205 (N-Nitrosodipropylamine)

3D SDF for HMDB0255205 (N-Nitrosodipropylamine)

3D-SDF for HMDB0255205 (N-Nitrosodipropylamine)

PDB for HMDB0255205 (N-Nitrosodipropylamine)

3D PDB for HMDB0255205 (N-Nitrosodipropylamine)

SMILES for HMDB0255205 (N-Nitrosodipropylamine)

INCHI for HMDB0255205 (N-Nitrosodipropylamine)

Structure for HMDB0255205 (N-Nitrosodipropylamine)

3D Structure for HMDB0255205 (N-Nitrosodipropylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra