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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:29:27 UTC

Update Date

2021-09-26 23:08:11 UTC

HMDB ID

HMDB0254282

Secondary Accession Numbers

None

Metabolite Identification

Common Name

m-Phenylenediamine

Description

1,3-phenylenediamine, also known as 1,3-diaminobenzene or 3-aminoaniline, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Based on a literature review a small amount of articles have been published on 1,3-phenylenediamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). M-phenylenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically m-Phenylenediamine 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
1,3-Benzenediamine	ChEBI
1,3-Diaminobenzene	ChEBI
3-Aminoaniline	ChEBI
3-Phenylenediamine	ChEBI
m-Diaminobenzene	ChEBI
m-Phenylenediamine	ChEBI
Meta-phenylenediamine	ChEBI
Diaminobenzene	Kegg
Benzenediamine	Kegg
1,3-Phenylenediamine	MeSH

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.144

Monoisotopic Molecular Weight

108.068748266

IUPAC Name

benzene-1,3-diamine

Traditional Name

developer C

CAS Registry Number

Not Available

SMILES

NC1=CC(N)=CC=C1

InChI Identifier

InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2

InChI Key

WZCQRUWWHSTZEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylenediamine (CHEBI:8092 )

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	0.01	ALOGPS
logP	0.32	ChemAxon
logS	-0.18	ALOGPS
pKa (Strongest Basic)	5.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.04 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.46 m³·mol⁻¹	ChemAxon
Polarizability	11.71 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
DeepCCS	[M+H]+	123.487	30932474
DeepCCS	[M-H]-	120.634	30932474
DeepCCS	[M-2H]-	157.293	30932474
DeepCCS	[M+Na]+	132.094	30932474
AllCCS	[M+H]+	123.9	32859911
AllCCS	[M+H-H2O]+	118.9	32859911
AllCCS	[M+NH4]+	128.5	32859911
AllCCS	[M+Na]+	129.8	32859911
AllCCS	[M-H]-	120.1	32859911
AllCCS	[M+Na-2H]-	122.7	32859911
AllCCS	[M+HCOO]-	125.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Phenylenediamine	NC1=CC(N)=CC=C1	2431.9	Standard polar	33892256
m-Phenylenediamine	NC1=CC(N)=CC=C1	1253.5	Standard non polar	33892256
m-Phenylenediamine	NC1=CC(N)=CC=C1	1299.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
m-Phenylenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N)=C1	1506.5	Semi standard non polar	33892256
m-Phenylenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N)=C1	1480.9	Standard non polar	33892256
m-Phenylenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N)=C1	1953.8	Standard polar	33892256
m-Phenylenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C)=C1	1631.0	Semi standard non polar	33892256
m-Phenylenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C)=C1	1656.4	Standard non polar	33892256
m-Phenylenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C)=C1	1742.8	Standard polar	33892256
m-Phenylenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C	1586.9	Semi standard non polar	33892256
m-Phenylenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C	1637.4	Standard non polar	33892256
m-Phenylenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C	1880.1	Standard polar	33892256
m-Phenylenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1673.3	Semi standard non polar	33892256
m-Phenylenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1724.3	Standard non polar	33892256
m-Phenylenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1704.0	Standard polar	33892256
m-Phenylenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1)[Si](C)(C)C	1701.0	Semi standard non polar	33892256
m-Phenylenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1)[Si](C)(C)C	1827.2	Standard non polar	33892256
m-Phenylenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1)[Si](C)(C)C	1623.3	Standard polar	33892256
m-Phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N)=C1	1722.4	Semi standard non polar	33892256
m-Phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N)=C1	1664.2	Standard non polar	33892256
m-Phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N)=C1	2094.2	Standard polar	33892256
m-Phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	2103.8	Semi standard non polar	33892256
m-Phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	2033.9	Standard non polar	33892256
m-Phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	1994.2	Standard polar	33892256
m-Phenylenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C(C)(C)C	1984.4	Semi standard non polar	33892256
m-Phenylenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C(C)(C)C	2035.8	Standard non polar	33892256
m-Phenylenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(N)=C1)[Si](C)(C)C(C)(C)C	2034.4	Standard polar	33892256
m-Phenylenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2297.8	Semi standard non polar	33892256
m-Phenylenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2298.4	Standard non polar	33892256
m-Phenylenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2073.2	Standard polar	33892256
m-Phenylenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1)[Si](C)(C)C(C)(C)C	2463.5	Semi standard non polar	33892256
m-Phenylenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1)[Si](C)(C)C(C)(C)C	2559.4	Standard non polar	33892256
m-Phenylenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1)[Si](C)(C)C(C)(C)C	2094.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - m-Phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-6a765c4ba0f2a1a1db67	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Phenylenediamine 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 - m-Phenylenediamine 10V, Positive-QTOF	splash10-0a4i-0900000000-639f570466c90ad7b907	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 20V, Positive-QTOF	splash10-0a4i-0900000000-8ad727e806fb7d3b0512	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 40V, Positive-QTOF	splash10-0159-9100000000-c484f2cfb03af2f9d8d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 10V, Negative-QTOF	splash10-0a4i-0900000000-d29409e93e9d75ca0739	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 20V, Negative-QTOF	splash10-0a4i-0900000000-d29409e93e9d75ca0739	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 40V, Negative-QTOF	splash10-0a4i-6900000000-c17c2079cb19aec5f3df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 10V, Positive-QTOF	splash10-0a4i-0900000000-0f7e6606314edbd6492a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 20V, Positive-QTOF	splash10-0a4i-1900000000-673fd4890b9a1527a8f2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 40V, Positive-QTOF	splash10-00lr-9100000000-3cb8b6e72a76109d64bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 10V, Negative-QTOF	splash10-0a4i-0900000000-1d4d8b4513a018558199	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 20V, Negative-QTOF	splash10-0a4i-2900000000-eaa12d6bc1d77dc4bc9e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Phenylenediamine 40V, Negative-QTOF	splash10-00kf-9000000000-332b6c9a5dcd6c98124c	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)	2021-10-25	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	¹H NMR Spectrum (1D, 300 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	¹³C NMR Spectrum (1D, 400 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, 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	¹H NMR Spectrum (1D, 700 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	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

13836283

KEGG Compound ID

C02454

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

M-Phenylenediamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8092

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 m-Phenylenediamine (HMDB0254282)

MOL for HMDB0254282 (m-Phenylenediamine)

3D MOL for HMDB0254282 (m-Phenylenediamine)

3D SDF for HMDB0254282 (m-Phenylenediamine)

3D-SDF for HMDB0254282 (m-Phenylenediamine)

PDB for HMDB0254282 (m-Phenylenediamine)

3D PDB for HMDB0254282 (m-Phenylenediamine)

SMILES for HMDB0254282 (m-Phenylenediamine)

INCHI for HMDB0254282 (m-Phenylenediamine)

Structure for HMDB0254282 (m-Phenylenediamine)

3D Structure for HMDB0254282 (m-Phenylenediamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra