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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:31 UTC
Update Date2023-02-21 17:20:35 UTC
HMDB IDHMDB0031469
Secondary Accession Numbers
  • HMDB31469
Metabolite Identification
Common Nametrans-Isoasarone
Descriptiontrans-Isoasarone, also known as asarone or cis-isoelemicin, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. trans-Isoasarone is found, on average, in the highest concentration within wild carrots (Daucus carota) and carrots (Daucus carota ssp. sativus). This could make trans-isoasarone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on trans-Isoasarone.
Structure
Data?1677000035
Synonyms
ValueSource
AsaroneChEBI
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzeneChEBI
trans-IsoasaronChEBI
Asarone, (e)-isomerMeSH
Asarone, (Z)-isomerMeSH
cis-IsoelemicinMeSH
gamma-AsaroneMeSH
(e)-AsaroneMeSH
(Z)-AsaroneMeSH
IsoasaroneMeSH
2,4,5-Trimethoxypropen-1-ylbenzeneMeSH
beta-AsaroneMeSH
cis-beta-AsaroneMeSH
cis-IsoasaroneMeSH
trans-AsaroneMeSH
trans-IsoasaroneChEBI
a-AsaronGenerator, HMDB
α-asaronGenerator, HMDB
(e)-2,4,5-TrimethoxypropenylbenzeneHMDB
1,2,4-Trimethoxy-5-(1-propenyl)-(e)-benzeneHMDB
1,2,4-Trimethoxy-5-propenyl-(e)-benzeneHMDB
1,2,4-Trimethoxy-5-propenyl-trans-benzeneHMDB
1,2,4-Trimethoxy-5-[(1E)-1-propenyl]benzeneHMDB
alpha-AsaroneHMDB
Isoasaron (6ci)HMDB
trans-(alpha )-AsaroneHMDB
trans-2,4,5-TrimethoxypropenylbenzeneHMDB
a-AsaroneGenerator
Α-asaroneGenerator
Chemical FormulaC12H16O3
Average Molecular Weight208.2536
Monoisotopic Molecular Weight208.109944378
IUPAC Name1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene
Traditional Nameasarone
CAS Registry Number2883-98-9
SMILES
COC1=CC(OC)=C(\C=C\C)C=C1OC
InChI Identifier
InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+
InChI KeyRKFAZBXYICVSKP-AATRIKPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point62 - 63 °CNot Available
Boiling Point296.00 to 297.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility101.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.406 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP3.35ALOGPS
logP2.62ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.81 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.51431661259
DarkChem[M-H]-150.21731661259
DeepCCS[M+H]+147.23130932474
DeepCCS[M-H]-144.87330932474
DeepCCS[M-2H]-179.68630932474
DeepCCS[M+Na]+154.73130932474
AllCCS[M+H]+146.432859911
AllCCS[M+H-H2O]+142.332859911
AllCCS[M+NH4]+150.332859911
AllCCS[M+Na]+151.432859911
AllCCS[M-H]-149.232859911
AllCCS[M+Na-2H]-149.932859911
AllCCS[M+HCOO]-150.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-IsoasaroneCOC1=CC(OC)=C(\C=C\C)C=C1OC2454.7Standard polar33892256
trans-IsoasaroneCOC1=CC(OC)=C(\C=C\C)C=C1OC1622.9Standard non polar33892256
trans-IsoasaroneCOC1=CC(OC)=C(\C=C\C)C=C1OC1702.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-Isoasarone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-1910000000-311a6eeb6d6e7b8cbd712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Isoasarone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Isoasarone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Positive-QTOFsplash10-0a4i-0190000000-43c2db0c78cd2c38866d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Positive-QTOFsplash10-0a4i-3890000000-8a310f43dfa83a6852fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Positive-QTOFsplash10-0gvo-5900000000-d8dec13738907307ac302016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Negative-QTOFsplash10-0a4i-0090000000-3260fe63f5df8a57e5012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Negative-QTOFsplash10-0a4m-0930000000-d48f45f13f4ba95211b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Negative-QTOFsplash10-0bt9-3900000000-ee6124b2b2fd1c4c5dc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Positive-QTOFsplash10-0a4i-0090000000-48e778bb33693fbfbece2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Positive-QTOFsplash10-0a4i-0390000000-20df49cd5d736b546ff72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Positive-QTOFsplash10-014i-9500000000-cb4f4e739e22509440dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Negative-QTOFsplash10-0a4i-0090000000-65fdf834be31e8e783102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Negative-QTOFsplash10-0a4i-0980000000-1b5b7322afb6d52db8452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Negative-QTOFsplash10-0a4i-8900000000-4428ce94cd47e6a5c9862021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008006
KNApSAcK IDC00042219
Chemspider ID552532
KEGG Compound IDC17846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsarone
METLIN IDNot Available
PubChem Compound636822
PDB IDNot Available
ChEBI ID78309
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1290501
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gracza L: [Constituents of Asarum europeum L. Communication No. 18. Dynamics of the synthesis of flavonoids]. Acta Pharm Hung. 1991 Mar;61(2):86-90. [PubMed:1887803 ]
  2. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .