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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:24:21 UTC

Update Date

2021-09-26 22:51:51 UTC

HMDB ID

HMDB0244231

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,5-Naphthalenediamine

Description

naphthalene-1,5-diamine, also known as 1,5-diaminonaphthalene, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review very few articles have been published on naphthalene-1,5-diamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,5-naphthalenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,5-Naphthalenediamine 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

HEADER    PROTEIN                                 20-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-16         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3    8   10                                                  
CONECT    8    4    7    9                                                  
CONECT    9    5    8   11                                                  
CONECT   10    6    7   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,5-Diaminonaphthalene	ChEBI
1,5-Naphthalenediamine	ChEBI
1,5-Naphthylenediamine	ChEBI

Chemical Formula

C₁₀H₁₀N₂

Average Molecular Weight

158.204

Monoisotopic Molecular Weight

158.08439833

IUPAC Name

naphthalene-1,5-diamine

Traditional Name

1,5-diaminonaphthalene

CAS Registry Number

Not Available

SMILES

NC1=CC=CC2=C1C=CC=C2N

InChI Identifier

InChI=1S/C10H10N2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6H,11-12H2

InChI Key

KQSABULTKYLFEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenediamine (CHEBI:53003 )

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	1.49	ALOGPS
logP	1.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	4.41	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	51.91 m³·mol⁻¹	ChemAxon
Polarizability	17.31 Å³	ChemAxon
Number of Rings	2	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]+	131.876	30932474
DeepCCS	[M-H]-	129.299	30932474
DeepCCS	[M-2H]-	165.677	30932474
DeepCCS	[M+Na]+	140.757	30932474
AllCCS	[M+H]+	134.5	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	138.8	32859911
AllCCS	[M+Na]+	140.0	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.5	32859911
AllCCS	[M+HCOO]-	134.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,5-Naphthalenediamine	NC1=CC=CC2=C1C=CC=C2N	2817.0	Standard polar	33892256
1,5-Naphthalenediamine	NC1=CC=CC2=C1C=CC=C2N	1789.3	Standard non polar	33892256
1,5-Naphthalenediamine	NC1=CC=CC2=C1C=CC=C2N	1936.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,5-Naphthalenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	1998.0	Semi standard non polar	33892256
1,5-Naphthalenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	1933.4	Standard non polar	33892256
1,5-Naphthalenediamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	2586.0	Standard polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C)C=CC=C12	2148.4	Semi standard non polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C)C=CC=C12	2055.0	Standard non polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C)C=CC=C12	2279.7	Standard polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C	2049.1	Semi standard non polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C	2016.4	Standard non polar	33892256
1,5-Naphthalenediamine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C	2425.9	Standard polar	33892256
1,5-Naphthalenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C)[Si](C)(C)C)C=CC=C12	2113.8	Semi standard non polar	33892256
1,5-Naphthalenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C)[Si](C)(C)C)C=CC=C12	2091.3	Standard non polar	33892256
1,5-Naphthalenediamine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C)[Si](C)(C)C)C=CC=C12	2190.3	Standard polar	33892256
1,5-Naphthalenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C2=CC=C1)[Si](C)(C)C	2123.4	Semi standard non polar	33892256
1,5-Naphthalenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C2=CC=C1)[Si](C)(C)C	2193.4	Standard non polar	33892256
1,5-Naphthalenediamine,4TMS,isomer #1	C[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C2=CC=C1)[Si](C)(C)C	2065.4	Standard polar	33892256
1,5-Naphthalenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	2226.0	Semi standard non polar	33892256
1,5-Naphthalenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	2126.9	Standard non polar	33892256
1,5-Naphthalenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N)C=CC=C12	2687.4	Standard polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C12	2581.6	Semi standard non polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C12	2450.9	Standard non polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C12	2514.9	Standard polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C(C)(C)C	2455.5	Semi standard non polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C(C)(C)C	2427.2	Standard non polar	33892256
1,5-Naphthalenediamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=C(N)C=CC=C12)[Si](C)(C)C(C)(C)C	2554.9	Standard polar	33892256
1,5-Naphthalenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C12	2741.8	Semi standard non polar	33892256
1,5-Naphthalenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C12	2708.3	Standard non polar	33892256
1,5-Naphthalenediamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C12	2533.1	Standard polar	33892256
1,5-Naphthalenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=C1)[Si](C)(C)C(C)(C)C	2939.8	Semi standard non polar	33892256
1,5-Naphthalenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=C1)[Si](C)(C)C(C)(C)C	2943.4	Standard non polar	33892256
1,5-Naphthalenediamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2C=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=C1)[Si](C)(C)C(C)(C)C	2496.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Naphthalenediamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-e19e2d21034de91a924a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Naphthalenediamine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 45V, Positive-QTOF	splash10-0a4i-0900000000-af6923d4b3ee11e71b2c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 60V, Positive-QTOF	splash10-0a4l-0900000000-0ece6b35abf4e74b662d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 45V, Positive-QTOF	splash10-0a4i-0900000000-285b4039b773c3af1757	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 15V, Positive-QTOF	splash10-0a4i-0900000000-6c64f460e1a1560b660f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 30V, Positive-QTOF	splash10-0a4i-0900000000-f93deea48079293badce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 90V, Positive-QTOF	splash10-066u-0900000000-150f0ca6e21fc80c70d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,5-Naphthalenediamine 75V, Positive-QTOF	splash10-0aou-0900000000-8635380bf2a5f2882d03	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 10V, Positive-QTOF	splash10-0a4l-0900000000-900e3391df632dcaea03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 20V, Positive-QTOF	splash10-0a4l-0900000000-e002982813be563b6079	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 40V, Positive-QTOF	splash10-014l-0900000000-1b385e9eec130f9c24da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 10V, Negative-QTOF	splash10-0a4i-0900000000-7ead900cc62c50f512d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 20V, Negative-QTOF	splash10-0a4i-0900000000-93018454245a964855c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 40V, Negative-QTOF	splash10-0a4i-0900000000-3ac8700904db7970a5fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 10V, Positive-QTOF	splash10-0a4i-0900000000-1a735aefd188aee0c047	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 20V, Positive-QTOF	splash10-0a4i-0900000000-f92ec3c1e20b8b1464c6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 40V, Positive-QTOF	splash10-0fai-1900000000-c11de370530ac472c745	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 10V, Negative-QTOF	splash10-0a4i-0900000000-935230cc04d215f10757	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 20V, Negative-QTOF	splash10-0a4i-0900000000-935230cc04d215f10757	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Naphthalenediamine 40V, Negative-QTOF	splash10-0pdi-0900000000-3c9bd216b411c51ec9c2	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

15851

KEGG Compound ID

C19463

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16720

PDB ID

Not Available

ChEBI ID

53003

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 1,5-Naphthalenediamine (HMDB0244231)

MOL for HMDB0244231 (1,5-Naphthalenediamine)

3D MOL for HMDB0244231 (1,5-Naphthalenediamine)

3D SDF for HMDB0244231 (1,5-Naphthalenediamine)

3D-SDF for HMDB0244231 (1,5-Naphthalenediamine)

PDB for HMDB0244231 (1,5-Naphthalenediamine)

3D PDB for HMDB0244231 (1,5-Naphthalenediamine)

SMILES for HMDB0244231 (1,5-Naphthalenediamine)

INCHI for HMDB0244231 (1,5-Naphthalenediamine)

Structure for HMDB0244231 (1,5-Naphthalenediamine)

3D Structure for HMDB0244231 (1,5-Naphthalenediamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra