Morusin (CHEM030293)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:47:51 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030293
Identification
Common NameMorusin
ClassSmall Molecule
DescriptionAn extended flavonoid that is flavone substituted by hydroxy groups at positions 5, 2' and 4', a prenyl group at position 3 and a 2,2-dimethyl pyran group across positions 7 and 8.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(2,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-2-butenyl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-oneHMDB
2-(2,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-2-butenyl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ciHMDB
MulberrochromeneHMDB
Chemical FormulaC25H24O6
Average Molecular Mass420.455 g/mol
Monoisotopic Mass420.157 g/mol
CAS Registry Number62596-29-6
IUPAC Name2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one
Traditional Namemorusin
SMILESCC(C)=CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=C(O)C=C(O)C=C1
InChI IdentifierInChI=1S/C25H24O6/c1-13(2)5-7-17-22(29)21-19(28)12-20-16(9-10-25(3,4)31-20)24(21)30-23(17)15-8-6-14(26)11-18(15)27/h5-6,8-12,26-28H,7H2,1-4H3
InChI KeyXFFOMNJIDRDDLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3-prenylated flavones
Alternative Parents
Substituents
  • 3-prenylated flavone
  • Pyranoflavonoid
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP4.88ALOGPS
logP5.22ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.87 m³·mol⁻¹ChemAxon
Polarizability45.47 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4228900000-2affcdcba17654d49f18Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1000039000-abf44c2ad584a39512b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1004900000-d0374f7defb8b22e4265Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-2009300000-0e88ace1138bfc449492Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066s-6294000000-80140a8ad408ae675a78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-70e4c74138be78101227Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0007900000-f45325771cf9e098fbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2947100000-e2f816db44a3bcad85f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-e89f00937a4f746a0b2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-e89f00937a4f746a0b2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0190100000-4ebaea6ef8aeb8df3495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-2c722d7f3ff1673a173fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000900000-2c722d7f3ff1673a173fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-0090400000-1353dd108cec26cf250eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036631
FooDB IDFDB015550
Phenol Explorer IDNot Available
KNApSAcK IDC00001070
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444990
ChEBI ID7005
PubChem Compound ID5281671
Kegg Compound IDC10106
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25237377
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25476160
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25628938
4. Lee JC, Won SJ, Chao CL, Wu FL, Liu HS, Ling P, Lin CN, Su CL: Morusin induces apoptosis and suppresses NF-kappaB activity in human colorectal cancer HT-29 cells. Biochem Biophys Res Commun. 2008 Jul 18;372(1):236-42. doi: 10.1016/j.bbrc.2008.05.023. Epub 2008 May 14.
5. de Souza MM, Bittar M, Cechinel-Filho V, Yunes RA, Messana I, Delle Monache F, Ferrari F: Antinociceptive properties of morusin, a prenylflavonoid isolated from Morus nigra root bark. Z Naturforsch C. 2000 Mar-Apr;55(3-4):256-60.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.