Cyclomulberrin (CHEM024699)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:52:06 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024699
Identification
Common NameCyclomulberrin
ClassSmall Molecule
DescriptionA extended flavonoid that is 6H,7H-chromeno[4,3-b]chromen-7-one which is substituted by a 2-methylprop-1-en-1-yl group at position 6, a 3-methylbut-2-en-1-yl group at position 11, and hydroxy groups at positions 3, 8, and 10. It is found in the bark of Morus species and has been reported to protect human neuronal cells derived from the human neuroblastoma SH-SY5Y cell line.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,8,10-Trihydroxy-11-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-7-one, 9ciHMDB
Chemical FormulaC25H24O6
Average Molecular Mass420.455 g/mol
Monoisotopic Mass420.157 g/mol
CAS Registry Number19275-51-5
IUPAC Name1,3,8-trihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one
Traditional Namecyclomulberrin
SMILESCC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O
InChI IdentifierInChI=1S/C25H24O6/c1-12(2)5-7-15-17(27)11-18(28)21-23(29)22-20(9-13(3)4)30-19-10-14(26)6-8-16(19)25(22)31-24(15)21/h5-6,8-11,20,26-28H,7H2,1-4H3
InChI KeySYFDWXWLRGHYAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassPyranoflavonoids
Direct ParentPyranoflavonoids
Alternative Parents
Substituents
  • Pyranoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.0077 g/LALOGPS
logP4.47ALOGPS
logP5.33ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.28 m³·mol⁻¹ChemAxon
Polarizability45.48 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, Positivesplash10-0a6u-3449500000-b0c4f508485b909ccc20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2000049000-7bc0dfe9b13feece76ffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1003900000-a8a0b37cb5840caad0e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3149300000-e243ed99e4d684dc3c97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9110100000-503470b143240bb8e9a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-006a3fbd24235bcbecdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0106900000-8d01ab175ce87619c15fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-3915100000-bf6aaab044167770d183Spectrum
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-0190200000-a1118abed2e9f1ffe42aSpectrum
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, Positivesplash10-00di-0091500000-3ae896b8f74c53ff643aSpectrum
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 IDHMDB0030688
FooDB IDFDB002607
Phenol Explorer IDNot Available
KNApSAcK IDC00004061
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9917576
ChEBI ID132869
PubChem Compound ID11742872
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19149258
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20815207
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22297755
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7903365
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8435100
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.