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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:02:03 UTC
Update Date2021-09-26 22:57:48 UTC
HMDB IDHMDB0247880
Secondary Accession NumbersNone
Metabolite Identification
Common Name(S)-3-(2-Methylphenoxy)propane-1,2-diol
Description(S)-3-(2-Methylphenoxy)propane-1,2-diol, also known as mephenesin or 1-(2-tolyl)glycerol, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Based on a literature review a significant number of articles have been published on (S)-3-(2-Methylphenoxy)propane-1,2-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (s)-3-(2-methylphenoxy)propane-1,2-diol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (S)-3-(2-Methylphenoxy)propane-1,2-diol 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
Thumb
Synonyms
ValueSource
1-(2-Tolyl)glycerolChEBI
1-(O-Tolyl)glycerolChEBI
MephenesinChEBI
TolserolKegg
Kade brand OF mephenesinHMDB
Sanofi synthelabo otc brand OF mephenesinHMDB
Dolo visano mHMDB
DécontractylHMDB
Mephenesin kade brandHMDB
Chemical FormulaC10H14O3
Average Molecular Weight182.219
Monoisotopic Molecular Weight182.094294311
IUPAC Name3-(2-methylphenoxy)propane-1,2-diol
Traditional Namemephenesin
CAS Registry NumberNot Available
SMILES
CC1=CC=CC=C1OCC(O)CO
InChI Identifier
InChI=1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3
InChI KeyJWDYCNIAQWPBHD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Toluene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.96ALOGPS
logP1.01ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.82 m³·mol⁻¹ChemAxon
Polarizability19.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+137.72730932474
DeepCCS[M-H]-134.60230932474
DeepCCS[M-2H]-171.37830932474
DeepCCS[M+Na]+146.91630932474
AllCCS[M+H]+140.932859911
AllCCS[M+H-H2O]+136.832859911
AllCCS[M+NH4]+144.832859911
AllCCS[M+Na]+145.932859911
AllCCS[M-H]-141.432859911
AllCCS[M+Na-2H]-142.432859911
AllCCS[M+HCOO]-143.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-3-(2-Methylphenoxy)propane-1,2-diolCC1=CC=CC=C1OCC(O)CO2186.5Standard polar33892256
(S)-3-(2-Methylphenoxy)propane-1,2-diolCC1=CC=CC=C1OCC(O)CO1547.5Standard non polar33892256
(S)-3-(2-Methylphenoxy)propane-1,2-diolCC1=CC=CC=C1OCC(O)CO1593.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol EI-B (Non-derivatized)splash10-0a4i-5900000000-3ce39ed63d61e07d52b52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-b7efb73b226cd03e49fa2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Positive-QTOFsplash10-001i-1900000000-931c8271d6fb5643cfc92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Positive-QTOFsplash10-069r-5900000000-2cb0895d9a4b0640f61f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Positive-QTOFsplash10-0a4i-9200000000-78c2e6485ea71c2622162016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Negative-QTOFsplash10-053r-0900000000-0a6d1982ba1d3a0753e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Negative-QTOFsplash10-0a4i-1900000000-608832f5bcea0fe354e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Negative-QTOFsplash10-0a4i-9700000000-bee7aa8f073d3e740ef72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Positive-QTOFsplash10-0a4i-2900000000-89f2644627652f40004f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Positive-QTOFsplash10-0a4l-9300000000-6e1a77602ee5ab89b1632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Positive-QTOFsplash10-0006-9000000000-bb8f781584ee22fd2df42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Negative-QTOFsplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Negative-QTOFsplash10-0a4i-9300000000-8864c588d454f239c30a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Negative-QTOFsplash10-0a4i-7900000000-ed674141cf39eafe84a22021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13583
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00052346
Chemspider ID3919
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMephenesin
METLIN IDNot Available
PubChem Compound4059
PDB IDNot Available
ChEBI ID94398
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]