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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:19:57 UTC

Update Date

2021-09-26 22:51:42 UTC

HMDB ID

HMDB0244147

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2,4,5-Tetramethylbenzene

Description

1,2,4,5-tetramethylbenzene, also known as 2,5-dimethyl-p-xylene or durol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 1,2,4,5-tetramethylbenzene is a sweet and rancid tasting compound. 1,2,4,5-tetramethylbenzene has been detected, but not quantified in, sweet cherries (Prunus avium). This could make 1,2,4,5-tetramethylbenzene a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1,2,4,5-tetramethylbenzene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2,4,5-tetramethylbenzene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2,4,5-Tetramethylbenzene 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

7269
  Mrv1652303202019012D          

 24 24  0  0  0  0            999 V2000
    3.0790    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215   -0.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.1615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058    1.2680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    1.0808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2522   -1.2680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.0808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7637   -0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.1615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244147

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C1=C(C(=C([H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3

> <INCHI_KEY>
SQNZJJAZBFDUTD-UHFFFAOYSA-N

> <FORMULA>
C10H14

> <MOLECULAR_WEIGHT>
134.222

> <EXACT_MASS>
134.109550451

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.154821923594206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,4,5-tetramethylbenzene

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.026931373333333

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
46.2228

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
durene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7269                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       5.747   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -3.080   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       7.908   1.247   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       3.587  -1.247   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       6.702   3.080   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       5.747   4.035   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.793   3.080   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.557   2.367   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       2.253   2.017   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.603   0.713   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       7.937  -2.367   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       9.242  -2.017   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       8.892  -0.713   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.793  -3.080   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.747  -4.035   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       6.702  -3.080   0.000  0.00  0.00           H+0
CONECT    1    2    5    7                                                  
CONECT    2    1    6    8                                                  
CONECT    3    4    5    9                                                  
CONECT    4    3    6   10                                                  
CONECT    5    1    3   11                                                  
CONECT    6    2    4   12                                                  
CONECT    7    1   13   14   15                                             
CONECT    8    2   16   17   18                                             
CONECT    9    3   19   20   21                                             
CONECT   10    4   22   23   24                                             
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20    9                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   10                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5-Dimethyl-p-xylene	ChEBI
Durol	ChEBI
Durene	Kegg

Chemical Formula

C₁₀H₁₄

Average Molecular Weight

134.222

Monoisotopic Molecular Weight

134.109550451

IUPAC Name

1,2,4,5-tetramethylbenzene

Traditional Name

durene

CAS Registry Number

Not Available

SMILES

[H]C1=C(C(=C([H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3

InChI Key

SQNZJJAZBFDUTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tetramethylbenzene (CHEBI:38978 )

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	4.05	ALOGPS
logP	4.03	ChemAxon
logS	-3.6	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	46.22 m³·mol⁻¹	ChemAxon
Polarizability	17.15 Å³	ChemAxon
Number of Rings	1	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+H]+	148.31	30932474
DeepCCS	[M-H]-	146.414	30932474
DeepCCS	[M-2H]-	179.754	30932474
DeepCCS	[M+Na]+	154.162	30932474
AllCCS	[M+H]+	122.1	32859911
AllCCS	[M+H-H2O]+	117.3	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.8	32859911
AllCCS	[M-H]-	124.3	32859911
AllCCS	[M+Na-2H]-	125.9	32859911
AllCCS	[M+HCOO]-	127.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,4,5-Tetramethylbenzene	[H]C1=C(C(=C([H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]	1788.9	Standard polar	33892256
1,2,4,5-Tetramethylbenzene	[H]C1=C(C(=C([H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]	1206.5	Standard non polar	33892256
1,2,4,5-Tetramethylbenzene	[H]C1=C(C(=C([H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]	1356.1	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 - 1,2,4,5-Tetramethylbenzene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,4,5-Tetramethylbenzene 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 - 1,2,4,5-Tetramethylbenzene 10V, Positive-QTOF	splash10-000i-0900000000-3b96f29d7e114d621b15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 20V, Positive-QTOF	splash10-000i-0900000000-e6ec6b16934bf1f3085a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 40V, Positive-QTOF	splash10-0gbi-9500000000-33ce2dc970c9f4153ede	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 10V, Negative-QTOF	splash10-001i-0900000000-aae599194ff67b3a064f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 20V, Negative-QTOF	splash10-001i-0900000000-aae599194ff67b3a064f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 40V, Negative-QTOF	splash10-001i-2900000000-36bb46b87512fc1af65d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 10V, Positive-QTOF	splash10-000i-1900000000-0c34302c1cb8b10769bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 20V, Positive-QTOF	splash10-00ku-9600000000-d3b4071db6c724a50dad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 40V, Positive-QTOF	splash10-0gdl-9200000000-e21625de7d728d0478ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 10V, Negative-QTOF	splash10-001i-0900000000-f5fa2e4eafb73a2ce5ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 20V, Negative-QTOF	splash10-001i-0900000000-581dd876f90826bbc9b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,5-Tetramethylbenzene 40V, Negative-QTOF	splash10-001i-2900000000-27241a356ae07a2d94f7	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

FDB029672

KNApSAcK ID

Not Available

Chemspider ID

6999

KEGG Compound ID

C14534

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Durene

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38978

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1144701

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 1,2,4,5-Tetramethylbenzene (HMDB0244147)

MOL for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

3D MOL for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

3D SDF for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

3D-SDF for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

PDB for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

3D PDB for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

SMILES for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

INCHI for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

Structure for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

3D Structure for HMDB0244147 (1,2,4,5-Tetramethylbenzene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra