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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:31 UTC
Update Date2018-03-12 22:08:41 UTC
HMDB IDHMDB0031469
Secondary Accession Numbers
  • HMDB31469
Metabolite Identification
Common Nametrans-Isoasarone
Descriptiontrans-Isoasarone, also known as asarone or isoasaron (6ci), belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. trans-Isoasarone exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, trans-isoasarone is primarily located in the membrane (predicted from logP). Outside of the human body, trans-isoasarone can be found in carrot and wild carrot. This makes trans-isoasarone a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
AsaroneChEBI
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzeneChEBI
trans-IsoasaronChEBI
trans-IsoasaroneChEBI
a-AsaronGenerator
α-asaronGenerator
(e)-2,4,5-TrimethoxypropenylbenzeneHMDB
(e)-AsaroneHMDB
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
trans-AsaroneHMDB
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
DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinols and derivatives. These are compounds containing a 1,2,4-trihydroxybenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentHydroxyquinols and derivatives
Alternative Parents
Substituents
  • Phenylpropene
  • Hydroxyquinol derivative
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point62 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-1910000000-311a6eeb6d6e7b8cbd71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-43c2db0c78cd2c38866dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3890000000-8a310f43dfa83a6852faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvo-5900000000-d8dec13738907307ac30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-3260fe63f5df8a57e501View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-0930000000-d48f45f13f4ba95211b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-3900000000-ee6124b2b2fd1c4c5dc2View in MoNA
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB008006
KNApSAcK IDNot Available
Chemspider ID552532
KEGG Compound IDC17846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound636822
PDB IDNot Available
ChEBI ID78309
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.. .