Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2018-01-25 19:29:20 UTC
Primary IDFDB002652
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDaphnetin
Description7,8-dihydroxy-2h-chromen-2-one, also known as daphnetin or 7,8-dihydroxycoumarin, is a member of the class of compounds known as 7,8-dihydroxycoumarins. 7,8-dihydroxycoumarins are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively. 7,8-dihydroxy-2h-chromen-2-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 7,8-dihydroxy-2h-chromen-2-one can be found in chickpea and watermelon, which makes 7,8-dihydroxy-2h-chromen-2-one a potential biomarker for the consumption of these food products.
CAS Number486-35-1
Structure
Thumb
Synonyms
SynonymSource
7,8-Dihydroxy-2H-1-benzopyran-2-oneChEBI
DaphnetinChEBI
DaphnetolChEBI
7,8-Dihydroxycoumarin, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility4.1 g/LALOGPS
logP1.49ALOGPS
logP1.83ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.51 m³·mol⁻¹ChemAxon
Polarizability16.23 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H6O4
IUPAC name7,8-dihydroxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
InChI KeyATEFPOUAMCWAQS-UHFFFAOYSA-N
Isomeric SMILESOC1=C(O)C2=C(C=CC(=O)O2)C=C1
Average Molecular Weight178.1415
Monoisotopic Molecular Weight178.02660868
Classification
Description belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7,8-dihydroxycoumarins
Alternative Parents
Substituents
  • 7,8-dihydroxycoumarin
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen 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 60.68%; H 3.39%; O 35.92%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4092000000-9e5038db7ca8b2f48a66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-0900000000-b6fd4c52b23487904db8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-0700d03e5ae6c4b59442View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-19dea9f6a73a24977e99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005i-8900000000-4e3f713c5e0fbdf7f377View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-a92e6e66acbf10b778dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8d9b4d2aefac4154e7c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-4e4784e5add130cd54cfView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMX24-U:CMX24-U
EAFUS IDNot Available
Dr. Duke IDDAPHNETIN
BIGG IDNot Available
KNApSAcK IDNot Available
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
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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
cholagogueDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
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
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).