Showing Compound Card for 7-Methoxycoumarin (CDB000545)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:42:55 UTC
Updated at2020-12-07 19:07:30 UTC
CannabisDB IDCDB000545
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name7-Methoxycoumarin
Description7-Methoxycoumarin or Herniarin, also known as ayapanin is a methoxy derivative of coumarin or a methyl derivative of umbelliferone. It 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). 7-Methoxycoumarin is a neutral, hydrophobic molecule that is not soluble in water. It exists as a white to pale yellow powder. It has a pleasant balsamic, sweet or tonka taste/odor. 7-Methoxycoumarin is used as a scent or aroma agent in perfumes, lotions, facial moisturizers, hand creams, hair conditioners, household aerosols, lip balms and baby oils. 7-Methoxycoumarin occurs naturally in many plants and foods and has been detected, but not quantified in, several different plants, such as hemp, barley, tarragons, roman camomiles, fruits, and wild celeries. This could make 7-methoxycoumarin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Methoxy-2H-1-benzopyran-2-oneChEBI
7-MethoxycoumarinChEBI
AyapaninChEBI
HerniarineChEBI
MethylumbelliferoneChEBI
7-(Methyloxy)-2H-chromen-2-oneHMDB
7-Methoxy-2H-1-benzopyran-2-one, 9ciHMDB
7-Methoxy-2H-chromen-2-oneHMDB
7-Methoxy-coumarinHMDB
7-METHOXYCOURMARINHMDB
7-Methyl ether derivative OF umbelliferoneHMDB
Coumarin, 7-methoxy- (8ci)HMDB
Herniarin (6ci)HMDB
Methyl umbelliferyl etherHMDB
Umbelliferone methyl etherHMDB
Chemical FormulaC10H8O3
Average Molecular Weight176.17
Monoisotopic Molecular Weight176.0473
IUPAC Name7-methoxy-2H-chromen-2-one
Traditional Namemethylumbelliferone
CAS Registry Number531-59-9
SMILES
COC1=CC2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3
InChI KeyLIIALPBMIOVAHH-UHFFFAOYSA-N
Chemical Taxonomy
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.13 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.88ALOGPS
logP1.63ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.01 m³·mol⁻¹ChemAxon
Polarizability17.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004j-3900000000-17e44e05c8fe2491778a2015-03-01View Spectrum
GC-MS7-Methoxycoumarin, non-derivatized, GC-MS Spectrumsplash10-005a-5900000000-a51cb4413d70fe3ecdccSpectrum
GC-MS7-Methoxycoumarin, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5b9073b915d724268702Spectrum
GC-MS7-Methoxycoumarin, non-derivatized, GC-MS Spectrumsplash10-005a-5900000000-a51cb4413d70fe3ecdccSpectrum
GC-MS7-Methoxycoumarin, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5b9073b915d724268702Spectrum
Predicted GC-MS7-Methoxycoumarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-0900000000-213046cadb13b2437780Spectrum
Predicted GC-MS7-Methoxycoumarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00e9-0900000000-4a3dcfd5346e0e2a65ca2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00e9-0900000000-e8134a5ce939ed3891102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00e9-0900000000-e8134a5ce939ed3891102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00b9-2900000000-8975e7f06b2c1779fc872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 12V, negativesplash10-03dl-5900000000-d235a93122ae0924491c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 15V, negativesplash10-03ec-7900000000-a0be9b4582f5680772392020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 22V, negativesplash10-03ec-9800000000-fb88eaf46b524a0103672020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-001i-4900000000-79f400e005b4b0abd2202020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-000l-9800000000-defb1852c01d2e5c38732020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0006-9600000000-0b4321e67197e681a6c62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-8662befff7041bc3c0192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9600000000-c8338c49921cebe4c8082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-5900000000-7d4b5b1155355c18e6802021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-a780bc6bc930a176af922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2a59cdf525e794c8bdd72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-6233a6992d4f3e8c7c6a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-0b88e2f92a1ca7f4b51c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9886d3e9db07e94c90082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fis-3900000000-e49193208460a6f4cf592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b25d33bd5abcda83159d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-bc4c58f50f3e417616c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-2900000000-6b0a0a442b520d5079b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-00ffe2c25b8beb0eeaa02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-3ab745d21b37980c43612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-7900000000-5a569237127af07c25c12021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029758
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000963
KNApSAcK IDC00002476
Chemspider ID10295
KEGG Compound IDC09268
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHerniarin
METLIN IDNot Available
PubChem Compound10748
PDB IDNot Available
ChEBI ID5679
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  2. Cheriyan BV Sr, Kadhirvelu P Sr, Nadipelly J Jr, Shanmugasundaram J, Sayeli V Sr, Subramanian V Sr: Anti-nociceptive Effect of 7-methoxy Coumarin from Eupatorium Triplinerve vahl (Asteraceae). Pharmacogn Mag. 2017 Jan-Mar;13(49):81-84. doi: 10.4103/0973-1296.197650. [PubMed:28216887 ]
  3. Kielbus M, Skalicka-Wozniak K, Grabarska A, Jeleniewicz W, Dmoszynska-Graniczka M, Marston A, Polberg K, Gawda P, Klatka J, Stepulak A: 7-substituted coumarins inhibit proliferation and migration of laryngeal cancer cells in vitro. Anticancer Res. 2013 Oct;33(10):4347-56. [PubMed:24123002 ]