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Showing metabocard for Toluene (HMDB0034168)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:57:44 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034168
Secondary Accession Numbers
  • HMDB34168
Metabolite Identification
Common NameToluene
DescriptionToluene, also known as methylbenzene or phenylmethane, belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. Toluene is a drug which is used for the removal of ascarids (toxocara canis and toxascaris leonina) and hookworms (ancylostoma caninum and uncinaria stenocephala) and as an aid in removing tapeworms (taenia pisiformis, dipylidium caninum, and echinococcus granulosus) from dogs and cats. Toluene is possibly neutral. Toluene exists in all living species, ranging from bacteria to humans. Toluene is a sweet and paint tasting compound. Toluene is found, on average, in the highest concentration within a few different foods, such as black walnuts, rosemaries, and corianders and in a lower concentration in milk (cow) and kohlrabis. Toluene has also been detected, but not quantified, in several different foods, such as prickly pears, citrus, yellow bell peppers, apples, and garden tomato (var.). This could make toluene a potential biomarker for the consumption of these foods. Toluene is a potentially toxic compound. Toluene, with regard to humans, has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, perillyl alcohol administration for cancer treatment, autism, and asthma; toluene has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034168 (Toluene)

  Mrv1652309272007442D          

  7  7  0  0  0  0            999 V2000
    0.5804    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0034168 (Toluene)

HMDB0034168
     RDKit          3D
Toluene
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.2118    0.0497   -0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106    0.0188   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334   -1.1792    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603   -1.2257    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965   -0.0594   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    1.1231   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    1.1912   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6052   -0.9233    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    0.7912    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    0.4066   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -2.0879    0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -2.1835    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1812   -0.1042   -0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    2.0432   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207    2.1393   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0034168 (Toluene)

  Mrv1652309272007442D          

  7  7  0  0  0  0            999 V2000
    0.5804    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034168

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3

> <INCHI_KEY>
YXFVVABEGXRONW-UHFFFAOYSA-N

> <FORMULA>
C7H8

> <MOLECULAR_WEIGHT>
92.1384

> <EXACT_MASS>
92.062600256

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.974244489174936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
toluene

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.486667205333333

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
31.0992

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
toluene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034168 (Toluene)

HMDB0034168
     RDKit          3D
Toluene
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.2118    0.0497   -0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106    0.0188   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334   -1.1792    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603   -1.2257    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965   -0.0594   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    1.1231   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    1.1912   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6052   -0.9233    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    0.7912    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    0.4066   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -2.0879    0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -2.1835    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1812   -0.1042   -0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    2.0432   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207    2.1393   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0034168 (Toluene)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.751   3.602   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0034168 (Toluene)

COMPND    HMDB0034168
HETATM    1  C1  UNL     1       2.212   0.050  -0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.711   0.019  -0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.033  -1.179   0.036  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.360  -1.226   0.033  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.097  -0.059  -0.013  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.399   1.123  -0.054  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.015   1.191  -0.052  1.00  0.00           C  
HETATM    8  H1  UNL     1       2.605  -0.923   0.314  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.578   0.791   0.766  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.578   0.407  -0.973  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.625  -2.088   0.072  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.847  -2.183   0.067  1.00  0.00           H  
HETATM   13  H6  UNL     1      -3.181  -0.104  -0.015  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.964   2.043  -0.090  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.521   2.139  -0.085  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    7
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7   15
END
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SMILES for HMDB0034168 (Toluene)

CC1=CC=CC=C1
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INCHI for HMDB0034168 (Toluene)

InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
MethylbenzeneChEBI
PhenylmethaneChEBI
ToluenChEBI
ToluolChEBI
Methyl-benzeneHMDB
Methylbenzene, 9ciHMDB
MethylbenzolHMDB
Monomethyl benzeneHMDB
Phenyl-methaneHMDB
Chemical FormulaC7H8
Average Molecular Weight92.1384
Monoisotopic Molecular Weight92.062600256
IUPAC Nametoluene
Traditional Nametoluene
CAS Registry Number108-88-3
SMILES
CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyYXFVVABEGXRONW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentToluenes
Alternative Parents
Substituents
  • Toluene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-95 °CNot Available
Boiling Point110.00 to 111.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.53 mg/mL at 25 °CNot Available
LogP2.73Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Asthma
  1. Dragonieri S, Schot R, Mertens BJ, Le Cessie S, Gauw SA, Spanevello A, Resta O, Willard NP, Vink TJ, Rabe KF, Bel EH, Sterk PJ: An electronic nose in the discrimination of patients with asthma and controls. J Allergy Clin Immunol. 2007 Oct;120(4):856-62. doi: 10.1016/j.jaci.2007.05.043. Epub 2007 Jul 20. [PubMed:17658592 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Perillyl alcohol administration for cancer treatment
  1. 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
DrugBank IDDB11558
Phenol Explorer Compound IDNot Available
FooDB IDFDB012454
KNApSAcK IDC00051588
Chemspider ID1108
KEGG Compound IDC01455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkToluene
METLIN IDNot Available
PubChem Compound1140
PDB IDMBN
ChEBI ID17578
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029826
Good Scents IDrw1290031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Biegert T, Fuchs G, Heider J: Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate. Eur J Biochem. 1996 Jun 15;238(3):661-8. [PubMed:8706665 ]
  2. Hougaard KS, Hansen AM, Hass U, Lund SP: Toluene depresses plasma corticosterone in pregnant rats. Pharmacol Toxicol. 2003 Mar;92(3):148-52. [PubMed:12753431 ]
  3. Tas U, Ogeturk M, Meydan S, Kus I, Kuloglu T, Ilhan N, Kose E, Sarsilmaz M: Hepatotoxic activity of toluene inhalation and protective role of melatonin. Toxicol Ind Health. 2011 Jun;27(5):465-73. doi: 10.1177/0748233710389853. Epub 2011 Feb 22. [PubMed:21343225 ]
  4. Aono J, Takimoto E, Komatsu T, Takeda A, Ueda W, Hirakawa M: [Anesthetic care of a patient intoxicated with thinner]. Masui. 1990 Mar;39(3):388-90. [PubMed:2345401 ]
  5. Win-Shwe TT, Mitsushima D, Nakajima D, Ahmed S, Yamamoto S, Tsukahara S, Kakeyama M, Goto S, Fujimaki H: Toluene induces rapid and reversible rise of hippocampal glutamate and taurine neurotransmitter levels in mice. Toxicol Lett. 2007 Jan 10;168(1):75-82. Epub 2006 Dec 4. [PubMed:17145141 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .