Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2018-05-28 23:08:46 UTC
Primary IDFDB002515
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOsthol
DescriptionOsthol, also known as 7-methoxy-8-(3-methylpent-2-enyl)coumarin, belongs to coumarins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Osthol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Osthol can be found in a number of food items such as wild celery, lemon, parsley, and wild carrot, which makes osthol a potential biomarker for the consumption of these food products. Osthol is an O-methylated coumarin. It is a calcium channel blocker, found in plants such as Cnidium monnieri, Angelica archangelica and Angelica pubescens .
CAS Number484-12-8
Structure
Thumb
Synonyms
SynonymSource
7-Methoxy-8-(3-methylpent-2-enyl)coumarinMeSH
2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)-biospider
7-Methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-onedb_source
7-Methoxy-8-(3-methyl-2-butenyl)-2H-chromen-2-onebiospider
7-Methoxy-8-(3-methyl-2-butenyl)-coumarinbiospider
7-Methoxy-8-(3-methyl-but-2-enyl)-chromen-2-onebiospider
7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-onebiospider
7-Methoxy-8-isopentenylcoumarinbiospider
7-Methoxy-8-prenylcoumarindb_source
8-(3-Methyl-2-butenyl)herniarinbiospider
Coumarin, 7-methoxy-8-(3-methyl-2-butenyl)-biospider
Coumarin, 7-methoxy-8-(3-mmtenyl)-biospider
Ostholdb_source
Ostholebiospider
Ostolbiospider
Ostolebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP3.41ALOGPS
logP3.35ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.25 m³·mol⁻¹ChemAxon
Polarizability26.34 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H16O3
IUPAC name7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
InChI IdentifierInChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
InChI KeyMBRLOUHOWLUMFF-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C2C=CC(=O)OC2=C1CC=C(C)C
Average Molecular Weight244.2857
Monoisotopic Molecular Weight244.109944378
Classification
DescriptionThis compound belongs to the class of chemical entities known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.75%; H 6.60%; O 19.65%DFC
Melting PointMp 85°DFC
Boiling PointNot Available
Experimental Water Solubility0.012 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data322 (e 18221) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-2fc5799b180de518e4efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-3190000000-257f4ccd908ffa56c6c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9820000000-11f5c9b9fcef5d41d09dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-a4fb35683e1aa8dd5101View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0490000000-81e15af3a3d9a535f2e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1920000000-570d40b95f6d7db0366fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0f9l-3970000000-4f98b2489c4119cf70b6View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09280
Pubchem Compound ID10228
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHGS93-C:CMF77-A
EAFUS IDNot Available
Dr. Duke IDOSTHOL|OSTHOLE
BIGG IDNot Available
KNApSAcK IDC00002488
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-lipoxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mitoticDUKE
anti mutagenicDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
juvabionalDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).