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Showing Compound Osthol (FDB002515)

Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2025-11-18 22:38:00 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
7-Methoxy-8-(3-methylpent-2-enyl)coumarinMeSH
OstholMeSH
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Description Belongs to the class of organic compounds 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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f9l-3970000000-4f98b2489c4119cf70b62015-03-01View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-2fc5799b180de518e4ef2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-3190000000-257f4ccd908ffa56c6c12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9820000000-11f5c9b9fcef5d41d09d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-a4fb35683e1aa8dd51012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0490000000-81e15af3a3d9a535f2e72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1920000000-570d40b95f6d7db0366f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0970000000-56ccbf122c5f7c9f4d8a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-9884c3353133eaaf2dd02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi3-9620000000-5f4ce0cf72069169ff7d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-204ca24ee8ee58d6cd7a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-0390000000-1cad35d7e2037c07eb0c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-0900000000-8b8323aa5449829b62782021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider ID9811
ChEMBL IDCHEMBL52229
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
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOsthol
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 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti mitoticAn agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Immunosuppressant35705 An agent that suppresses the immune system, reducing inflammation and preventing rejection in organ transplants, and treating autoimmune diseases such as rheumatoid arthritis and lupus.DUKE
JuvabionalA regulator of insect development, reproduction, and growth, juvenile hormone inhibitor, used in pest control and insecticide development, with potential applications in agriculture and entomology.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.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).