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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:23:29 UTC

Update Date

2021-09-26 22:51:49 UTC

HMDB ID

HMDB0244215

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,4-Dimethylnaphthalene

Description

1,4-Dimethylnapthalene, also known as 1,4-DMN, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1,4-Dimethylnapthalene has been detected, but not quantified in, potatos (Solanum tuberosum). This could make 1,4-dimethylnapthalene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,4-Dimethylnapthalene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,4-dimethylnaphthalene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,4-Dimethylnaphthalene 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   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  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    1    5                                                  
CONECT   11    9                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-DMN	ChEBI

Chemical Formula

C₁₂H₁₂

Average Molecular Weight

156.2237

Monoisotopic Molecular Weight

156.093900384

IUPAC Name

1,4-dimethylnaphthalene

Traditional Name

1,4-dimethylnaphthalene

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H12/c1-9-7-8-10(2)12-6-4-3-5-11(9)12/h3-8H,1-2H3

InChI Key

APQSQLNWAIULLK-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
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

dimethylnaphthalene (CHEBI:48609 )

Ontology

Not Available

Exogenous (FooDB: )

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

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	4.37	ALOGPS
logP	3.99	ChemAxon
logS	-4.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.59 m³·mol⁻¹	ChemAxon
Polarizability	18.7 Å³	ChemAxon
Number of Rings	2	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-2H]-	168.171	30932474
DeepCCS	[M+Na]+	143.709	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.04 minutes	32390414
Predicted by Siyang on May 30, 2022	18.5927 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2313.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	704.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	268.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	463.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	830.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	757.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	162.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1479.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	729.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1814.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	523.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	578.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	440.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Dimethylnaphthalene	CC1=CC=C(C)C2=CC=CC=C12	2061.1	Standard polar	33892256
1,4-Dimethylnaphthalene	CC1=CC=C(C)C2=CC=CC=C12	1424.6	Standard non polar	33892256
1,4-Dimethylnaphthalene	CC1=CC=C(C)C2=CC=CC=C12	1452.9	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 - 1,4-Dimethylnaphthalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-3cba5d8a8fb3b72e4803	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Dimethylnaphthalene 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 - 1,4-Dimethylnaphthalene 10V, Positive-QTOF	splash10-0a4i-0900000000-0516af96d145d7351575	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 20V, Positive-QTOF	splash10-0a4i-0900000000-f4fb7641d8b6536178f3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 40V, Positive-QTOF	splash10-0pec-2900000000-c899ad8bd8d297b44a17	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 10V, Negative-QTOF	splash10-0a4i-0900000000-4fa75fdaf96be705bf1c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 20V, Negative-QTOF	splash10-0a4i-0900000000-4fa75fdaf96be705bf1c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 40V, Negative-QTOF	splash10-0a4i-0900000000-4e4d040caa22eb4fcee9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 10V, Positive-QTOF	splash10-0a4i-0900000000-ddab12af8993bc2fb56c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 20V, Positive-QTOF	splash10-0a4i-0900000000-c6e6efc9227bc227d1af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 40V, Positive-QTOF	splash10-002f-3900000000-0c07337fe7f447751a0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 10V, Negative-QTOF	splash10-0a4i-0900000000-4e868adf7649a278b06c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 20V, Negative-QTOF	splash10-0a4i-0900000000-4e868adf7649a278b06c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dimethylnaphthalene 40V, Negative-QTOF	splash10-056r-0900000000-f4a497e74ea3e54f2213	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

FDB007065

KNApSAcK ID

Not Available

Chemspider ID

10829

KEGG Compound ID

Not Available

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

48609

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1149031

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 1,4-Dimethylnaphthalene (HMDB0244215)

MOL for HMDB0244215 (1,4-Dimethylnaphthalene)

3D MOL for HMDB0244215 (1,4-Dimethylnaphthalene)

3D SDF for HMDB0244215 (1,4-Dimethylnaphthalene)

3D-SDF for HMDB0244215 (1,4-Dimethylnaphthalene)

PDB for HMDB0244215 (1,4-Dimethylnaphthalene)

3D PDB for HMDB0244215 (1,4-Dimethylnaphthalene)

SMILES for HMDB0244215 (1,4-Dimethylnaphthalene)

INCHI for HMDB0244215 (1,4-Dimethylnaphthalene)

Structure for HMDB0244215 (1,4-Dimethylnaphthalene)

3D Structure for HMDB0244215 (1,4-Dimethylnaphthalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra