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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:37 UTC
Update Date2019-07-23 06:09:34 UTC
HMDB IDHMDB0031811
Secondary Accession Numbers
  • HMDB31811
Metabolite Identification
Common Name3,5-Dimethylphenyl methylcarbamate
Description3,5-Dimethylphenyl methylcarbamate, also known as 3,5-xylenyl N-methylcarbamic acid or 3,5-XMC, belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. 3,5-Dimethylphenyl methylcarbamate is a moderately basic compound (based on its pKa). 3,5-Dimethylphenyl methylcarbamate is a carbamate pesticide. 3,5-Dimethylphenyl methylcarbamate is a potentially toxic compound. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. For skin contact, the skin should be washed with soap and water.
Structure
Data?1563862174
Synonyms
ValueSource
3,5-Dimethylphenyl N-methylcarbamateChEBI
3,5-XMCChEBI
3,5-Xylenol, methylcarbamateChEBI
3,5-Xylenyl N-methylcarbamateChEBI
3,5-Xylyl methylcarbamateChEBI
3,5-Xylyl N-methylcarbamateChEBI
Methylcarbamic acid 3,5-xylyl esterChEBI
N-Methyl-3,5-xylyl carbamateChEBI
CosbanKegg
3,5-Dimethylphenyl N-methylcarbamic acidGenerator
3,5-Xylenol, methylcarbamic acidGenerator
3,5-Xylenyl N-methylcarbamic acidGenerator
3,5-Xylyl methylcarbamic acidGenerator
3,5-Xylyl N-methylcarbamic acidGenerator
Methylcarbamate 3,5-xylyl esterGenerator
N-Methyl-3,5-xylyl carbamic acidGenerator
3,5-Dimethylphenyl methylcarbamic acidGenerator
3,5-Dimethylphenol methylcarbamateHMDB
3,5-Dimethylphenyl methylcarbamate (9ci)HMDB
3,5-Xylyl methylcarbamate (8ci)HMDB
3,5-Xylylester kyseliny methylkarbaminoveHMDB
Carbamic acid, methyl-, 3,5-xylyl esterHMDB
CarbaronHMDB
MacbalHMDB
MaqbalHMDB
MaqbarlHMDB
Phenol, 3,5-dimethyl-, methylcarbamateHMDB
Phenol, 3,5-dimethyl-, methylcarbamate (9ci)HMDB
ProfamHMDB
XMCHMDB
XMC (Pesticide)HMDB
XMC, JMAFHMDB
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name1-(3,5-dimethylphenoxy)-N-methylmethanimidic acid
Traditional Name1-3,5-dimethylphenoxy-N-methylmethanimidic acid
CAS Registry Number2655-14-3
SMILES
CN=C(O)OC1=CC(C)=CC(C)=C1
InChI Identifier
InChI=1S/C10H13NO2/c1-7-4-8(2)6-9(5-7)13-10(12)11-3/h4-6H,1-3H3,(H,11,12)
InChI KeyCVQODEWAPZVVBU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenyl methylcarbamates
Direct ParentPhenyl methylcarbamates
Alternative Parents
Substituents
  • Phenyl methylcarbamate
  • Phenoxy compound
  • M-xylene
  • Xylene
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.47 mg/mL at 20 °CNot Available
LogP2.23Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP2.58ALOGPS
logP3.01ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.37 m³·mol⁻¹ChemAxon
Polarizability19.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-d5c3befe3fd184c3a873Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9710000000-06a89c21aa5b904a2bf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-2900000000-93ff4c82de47a758e71aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-0dda7bcc121722b5dfc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9600000000-6fc9a4f2cba7f186ba83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7900000000-e4100dbc978665ab49deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-6900000000-4db5db70b9a4d49d844aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-5900000000-ec733a3b1746778e68b7Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-3900000000-2795d7a07d334bd50bffSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008485
KNApSAcK IDNot Available
Chemspider ID16606
KEGG Compound IDC18771
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17563
PDB IDNot Available
ChEBI ID38571
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .