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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:00:58 UTC

Update Date

2022-03-07 03:17:35 UTC

HMDB ID

HMDB0059733

Secondary Accession Numbers

HMDB59733

Metabolite Identification

Common Name

1,4,5-Trimethyl-naphtalene

Description

1,4,5-Trimethyl-naphtalene belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1,4,5-Trimethyl-naphtalene is possibly neutral. 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   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    9                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0059733
HETATM    1  C1  UNL     1       3.420  -0.111   0.047  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.980  -0.555   0.026  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.654  -1.878   0.023  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.338  -2.243   0.004  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.726  -1.310  -0.013  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.108  -1.750  -0.029  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.382   0.024  -0.011  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.354   0.995  -0.028  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.772   0.669  -0.055  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.919   2.336  -0.024  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.406   2.703  -0.004  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.344   1.729   0.012  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.985   0.394   0.009  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.673   0.440  -0.863  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.088  -0.977   0.221  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.593   0.568   0.932  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.427  -2.618   0.036  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.012  -3.280  -0.003  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.578  -1.920  -1.008  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.020  -2.892   0.221  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.741  -1.529   0.835  1.00  0.00           H  
HETATM   22  H9  UNL     1      -3.277   1.702  -0.300  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.173   0.162  -0.932  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.282   0.561   0.912  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.701   3.080  -0.036  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.704   3.743  -0.001  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.408   1.960   0.029  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   13
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6    7
CONECT    6   19   20   21
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   22   23   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
145-Trimethylnaphthalene	HMDB

Chemical Formula

C₁₃H₁₄

Average Molecular Weight

170.2503

Monoisotopic Molecular Weight

170.109550448

IUPAC Name

1,4,5-trimethylnaphthalene

Traditional Name

1,4,5-trimethylnaphthalene

CAS Registry Number

Not Available

SMILES

CC1=CC=CC2=C(C)C=CC(C)=C12

InChI Identifier

InChI=1S/C13H14/c1-9-7-8-11(3)13-10(2)5-4-6-12(9)13/h4-8H,1-3H3

InChI Key

FSAWRQYDMHSDRN-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

Not Available

Ontology

Not Available

Urine (PMID: 22284503)

Cellular substructure

Membrane (HMDB: HMDB0059733)

Source

Exogenous

Exogenous (HMDB: HMDB0059733)

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	0.0011 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.5	ChemAxon
logS	-5.2	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	57.63 m³·mol⁻¹	ChemAxon
Polarizability	20.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	138.632	31661259
DarkChem	[M-H]-	136.65	31661259
DeepCCS	[M-2H]-	175.325	30932474
DeepCCS	[M+Na]+	150.863	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	136.2	32859911
AllCCS	[M+Na-2H]-	136.4	32859911
AllCCS	[M+HCOO]-	136.7	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.	7.41 minutes	32390414
Predicted by Siyang on May 30, 2022	19.5091 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2318.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	749.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	281.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	496.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	900.9 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	782.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	168.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1643.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	744.0 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	1829.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	564.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	531.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	552.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	453.1 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	10.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4,5-Trimethyl-naphtalene	CC1=CC=CC2=C(C)C=CC(C)=C12	2193.2	Standard polar	33892256
1,4,5-Trimethyl-naphtalene	CC1=CC=CC2=C(C)C=CC(C)=C12	1541.6	Standard non polar	33892256
1,4,5-Trimethyl-naphtalene	CC1=CC=CC2=C(C)C=CC(C)=C12	1587.2	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 - 1,4,5-Trimethyl-naphtalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-0900000000-79cbca2cde232bf4a83f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Trimethyl-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 - 1,4,5-Trimethyl-naphtalene 10V, Positive-QTOF	splash10-00di-0900000000-abf3dccdb40fe714ba2e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 20V, Positive-QTOF	splash10-00di-0900000000-d11246abb99609661e5a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 40V, Positive-QTOF	splash10-0a4l-1900000000-de729edd08269cbf3e85	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 10V, Negative-QTOF	splash10-014i-0900000000-cf8e934b052b230c1ca8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 20V, Negative-QTOF	splash10-014i-0900000000-00ad2ba10a4627978260	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 40V, Negative-QTOF	splash10-014i-0900000000-2dd8d00b8731c069fdb4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 10V, Positive-QTOF	splash10-00di-0900000000-55cfdaa9b3d5faef96e4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 20V, Positive-QTOF	splash10-00di-0900000000-0704ada517797d22708c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 40V, Positive-QTOF	splash10-016r-1900000000-08b436a9c3a745e3b61e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 10V, Negative-QTOF	splash10-014i-0900000000-00359992de7a4c09d9af	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 20V, Negative-QTOF	splash10-014i-0900000000-00359992de7a4c09d9af	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trimethyl-naphtalene 40V, Negative-QTOF	splash10-014i-0900000000-c23f1937a6fec5e5c67b	2021-09-25	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16478

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

Not Available

Showing metabocard for 1,4,5-Trimethyl-naphtalene (HMDB0059733)

MOL for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

3D MOL for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

3D SDF for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

3D-SDF for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

PDB for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

3D PDB for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

SMILES for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

INCHI for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

Structure for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

3D Structure for HMDB0059733 (1,4,5-Trimethyl-naphtalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra