Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:02:53 UTC

Update Date

2022-03-07 03:17:36 UTC

HMDB ID

HMDB0059764

Secondary Accession Numbers

HMDB59764

Metabolite Identification

Common Name

2,6-Dimethyl-naphtalene

Description

2,6-Dimethyl-naphtalene, also known as 2,6-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. 2,6-Dimethyl-naphtalene is possibly neutral. 2,6-Dimethyl-naphtalene is a grass tasting compound. Outside of the human body,. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-DMN	ChEBI
2,6-Dimethylnaphthalene picrate	HMDB
2,6-Dimethylnaphthalene ion (1-)	HMDB

Chemical Formula

C₁₂H₁₂

Average Molecular Weight

156.2237

Monoisotopic Molecular Weight

156.093900384

IUPAC Name

2,6-dimethylnaphthalene

Traditional Name

2,6-dimethylnaphthalene

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C=C1)C=C(C)C=C2

InChI Identifier

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

InChI Key

YGYNBBAUIYTWBF-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:34251 )

Ontology

Not Available

Urine (PMID: 22284503)

Cellular substructure

Membrane (HMDB: HMDB0059764)

Source

Exogenous

Exogenous (HMDB: HMDB0059764)

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
Water Solubility	0.0047 g/L	ALOGPS
logP	4.37	ALOGPS
logP	3.99	ChemAxon
logS	-4.5	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	19.04 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
DarkChem	[M+H]+	135.868	31661259
DarkChem	[M-H]-	133.005	31661259
DeepCCS	[M+H]+	140.444	30932474
DeepCCS	[M-H]-	137.691	30932474
DeepCCS	[M-2H]-	173.569	30932474
DeepCCS	[M+Na]+	149.107	30932474
AllCCS	[M+H]+	128.0	32859911
AllCCS	[M+H-H2O]+	123.2	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.8	32859911
AllCCS	[M-H]-	132.9	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	133.9	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	7.24 minutes	32390414
Predicted by Siyang on May 30, 2022	18.0704 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1986.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	660.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	250.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	431.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	815.8 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	740.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1384.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	737.5 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	1895.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	495.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	573.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	382.4 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	16.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethyl-naphtalene	CC1=CC2=C(C=C1)C=C(C)C=C2	2047.6	Standard polar	33892256
2,6-Dimethyl-naphtalene	CC1=CC2=C(C=C1)C=C(C)C=C2	1397.4	Standard non polar	33892256
2,6-Dimethyl-naphtalene	CC1=CC2=C(C=C1)C=C(C)C=C2	1397.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-naphtalene EI-B (Non-derivatized)	splash10-0a6r-6900000000-bd5a0ebc7638e9444780	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-naphtalene EI-B (Non-derivatized)	splash10-0a6r-6900000000-bd5a0ebc7638e9444780	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-naphtalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-141d53fc0addd0623871	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-naphtalene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-naphtalene 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 - 2,6-Dimethyl-naphtalene 10V, Positive-QTOF	splash10-0a4i-0900000000-1fa175c6bd6f165a7d9a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 20V, Positive-QTOF	splash10-0a4i-0900000000-209cb16230dbf7522262	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 40V, Positive-QTOF	splash10-0a4i-1900000000-f5a8d8372cc25849ad95	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 10V, Negative-QTOF	splash10-0a4i-0900000000-1bb747017a8f434c1826	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 20V, Negative-QTOF	splash10-0a4i-0900000000-1bb747017a8f434c1826	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 40V, Negative-QTOF	splash10-0a4i-0900000000-66e4bd8da2da00c03a83	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 10V, Negative-QTOF	splash10-0a4i-0900000000-4e868adf7649a278b06c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 20V, Negative-QTOF	splash10-0a4i-0900000000-4e868adf7649a278b06c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 40V, Negative-QTOF	splash10-0a6r-0900000000-1616135019f652a409b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 10V, Positive-QTOF	splash10-0a4i-0900000000-ddab12af8993bc2fb56c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 20V, Positive-QTOF	splash10-0a4i-0900000000-f3a72719b2081521aabc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-naphtalene 40V, Positive-QTOF	splash10-0fr6-4900000000-4adb961dfdf957ee1730	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029752

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14330

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,6-Dimethylnaphthalene

METLIN ID

Not Available

PubChem Compound

11387

PDB ID

Not Available

ChEBI ID

34251

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

Essumang DK: Distribution, levels, and risk assessment of polycyclic aromatic hydrocarbons (PAHs) in some water bodies along the coastal belt of Ghana. ScientificWorldJournal. 2010 Jun 1;10:972-85. doi: 10.1100/tsw.2010.96. [PubMed:20526527 ]

Showing metabocard for 2,6-Dimethyl-naphtalene (HMDB0059764)

MOL for HMDB0059764 (2,6-Dimethyl-naphtalene)

3D MOL for HMDB0059764 (2,6-Dimethyl-naphtalene)

3D SDF for HMDB0059764 (2,6-Dimethyl-naphtalene)

3D-SDF for HMDB0059764 (2,6-Dimethyl-naphtalene)

PDB for HMDB0059764 (2,6-Dimethyl-naphtalene)

3D PDB for HMDB0059764 (2,6-Dimethyl-naphtalene)

SMILES for HMDB0059764 (2,6-Dimethyl-naphtalene)

INCHI for HMDB0059764 (2,6-Dimethyl-naphtalene)

Structure for HMDB0059764 (2,6-Dimethyl-naphtalene)

3D Structure for HMDB0059764 (2,6-Dimethyl-naphtalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra