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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:02:56 UTC

Update Date

2021-09-26 22:54:48 UTC

HMDB ID

HMDB0246005

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,3'-Iminodipropionitrile

Description

3,3'-Iminodipropionitrile, also known as bis(2-cyanoethyl)amine or crotonitrile, belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N. Based on a literature review a significant number of articles have been published on 3,3'-Iminodipropionitrile. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,3'-iminodipropionitrile is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,3'-Iminodipropionitrile 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
Crotonitrile	HMDB
3,3'-Iminodipropionitrile monohydrochloride	HMDB
Bis(2-cyanoethyl)amine	HMDB
beta,Beta'-iminodipropionitrile	HMDB
Bis-(2-cyanoethyl)amine	HMDB
Bis(beta-cyanoethyl)amine	HMDB
3,3'-Iminobispropanenitrile	HMDB
3,3'-Iminodipropionitrile fumarate	HMDB
3,3'-Iminodipropionitrile sulfate (1:1)	HMDB
3,3'-Iminodipropionitrile	MeSH

Chemical Formula

C₆H₉N₃

Average Molecular Weight

123.159

Monoisotopic Molecular Weight

123.079647302

IUPAC Name

3-[(2-cyanoethyl)amino]propanenitrile

Traditional Name

propanenitrile, 3,3'-iminobis-

CAS Registry Number

Not Available

SMILES

N#CCCNCCC#N

InChI Identifier

InChI=1S/C6H9N3/c7-3-1-5-9-6-2-4-8/h9H,1-2,5-6H2

InChI Key

SBAJRGRUGUQKAF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Organic cyanides

Direct Parent

Nitriles

Alternative Parents

Substituents

Secondary amine
Nitrile
Carbonitrile
Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-0.32	ALOGPS
logP	-0.65	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	5.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.22 m³·mol⁻¹	ChemAxon
Polarizability	13.51 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]+	131.059	30932474
DeepCCS	[M-H]-	128.939	30932474
DeepCCS	[M-2H]-	164.505	30932474
DeepCCS	[M+Na]+	139.159	30932474
AllCCS	[M+H]+	128.0	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	132.4	32859911
AllCCS	[M+HCOO]-	135.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Iminodipropionitrile	N#CCCNCCC#N	1654.0	Standard polar	33892256
3,3'-Iminodipropionitrile	N#CCCNCCC#N	1191.0	Standard non polar	33892256
3,3'-Iminodipropionitrile	N#CCCNCCC#N	1380.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Iminodipropionitrile,1TMS,isomer #1	C[Si](C)(C)N(CCC#N)CCC#N	1494.2	Semi standard non polar	33892256
3,3'-Iminodipropionitrile,1TMS,isomer #1	C[Si](C)(C)N(CCC#N)CCC#N	1458.5	Standard non polar	33892256
3,3'-Iminodipropionitrile,1TMS,isomer #1	C[Si](C)(C)N(CCC#N)CCC#N	2413.1	Standard polar	33892256
3,3'-Iminodipropionitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC#N)CCC#N	1688.3	Semi standard non polar	33892256
3,3'-Iminodipropionitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC#N)CCC#N	1708.2	Standard non polar	33892256
3,3'-Iminodipropionitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC#N)CCC#N	2475.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Iminodipropionitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-9000000000-8658565140e65a619132	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Iminodipropionitrile 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 - 3,3'-Iminodipropionitrile 10V, Positive-QTOF	splash10-00di-2900000000-484a5f7336c511f90257	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 20V, Positive-QTOF	splash10-0pb9-9600000000-1341cb5b99780ac113f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 40V, Positive-QTOF	splash10-0udi-9000000000-61e1df309fdcb127fced	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 10V, Negative-QTOF	splash10-00di-1900000000-3d067b4ab5b75c237483	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 20V, Negative-QTOF	splash10-00xr-8900000000-ebc6b54b28a91d9680ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 40V, Negative-QTOF	splash10-0gbc-9000000000-6ff3a98d6e93717af0b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 10V, Positive-QTOF	splash10-05aj-9100000000-2ec538000cc492869178	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 20V, Positive-QTOF	splash10-000x-9000000000-547f7a336c7ac2db6735	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 40V, Positive-QTOF	splash10-0zfr-9000000000-a55055cddc7f63d8e2b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 10V, Negative-QTOF	splash10-00di-0900000000-a685f1bf29026b33951e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 20V, Negative-QTOF	splash10-066r-9700000000-aa2353874eac7aae6712	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Iminodipropionitrile 40V, Negative-QTOF	splash10-014i-9000000000-c2b88fd0831ba24f2e74	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

7857

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8149

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 3,3'-Iminodipropionitrile (HMDB0246005)

MOL for HMDB0246005 (3,3'-Iminodipropionitrile)

3D MOL for HMDB0246005 (3,3'-Iminodipropionitrile)

3D SDF for HMDB0246005 (3,3'-Iminodipropionitrile)

3D-SDF for HMDB0246005 (3,3'-Iminodipropionitrile)

PDB for HMDB0246005 (3,3'-Iminodipropionitrile)

3D PDB for HMDB0246005 (3,3'-Iminodipropionitrile)

SMILES for HMDB0246005 (3,3'-Iminodipropionitrile)

INCHI for HMDB0246005 (3,3'-Iminodipropionitrile)

Structure for HMDB0246005 (3,3'-Iminodipropionitrile)

3D Structure for HMDB0246005 (3,3'-Iminodipropionitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra