Cyclomorusin (CHEM024698)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:52:04 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024698
Identification
Common NameCyclomorusin
ClassSmall Molecule
DescriptionAn extended flavonoid that is cyclomulberrin in which the hydroxy group at position 10 has undergone oxidative cyclisation to position 3 of the 3-methylbut-2-en-1-yl substituent, with migration of the double bond into conjugation with the aromatic ring. It is a moderate inhibitor of acetylcholinesterase (IC50 = 16.2 - 36.6 muM), and a strong inhibitor of platelet-activating factor (PAF; 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) induced platelet aggregation.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-oneHMDB
6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one, 9ciHMDB
Cyclomorusin aHMDB
CyclomulberrochromeneHMDB
Chemical FormulaC25H22O6
Average Molecular Mass418.439 g/mol
Monoisotopic Mass418.142 g/mol
CAS Registry Number62596-34-3
IUPAC Name11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-en-1-yl)-2,8,16-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one
Traditional Namecyclomorusin
SMILESCC(C)=CC1OC2=C(C=CC(O)=C2)C2=C1C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O
InChI IdentifierInChI=1S/C25H22O6/c1-12(2)9-19-21-22(28)20-16(27)11-18-15(7-8-25(3,4)31-18)23(20)30-24(21)14-6-5-13(26)10-17(14)29-19/h5-11,19,26-27H,1-4H3
InChI KeyGDQXJMLXEYSICD-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
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility0.0055 g/LALOGPS
logP4.3ALOGPS
logP4.81ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.42ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity118.45 m³·mol⁻¹ChemAxon
Polarizability45.13 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-5484900000-9c42636be55abff06860Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-4361390000-c990954f5ce4e5821cfcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1001900000-f73a2686012c257315e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-2009500000-48d44245d95216342a2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067l-9104000000-6f33223106ab7c45d7fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-c21f5b6b75e086dacbe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1007900000-15e21879c2756f5cf25aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3559000000-9db52e1da60107146013Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-05dfc1131f8b02e9e947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000900000-05dfc1131f8b02e9e947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0091500000-0d10a6740d3052cdb546Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-0c2e3c045664a8c8905aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-0c2e3c045664a8c8905aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0190200000-765161ea5d98ac18c93bSpectrum
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 IDHMDB0030687
FooDB IDFDB002606
Phenol Explorer IDNot Available
KNApSAcK IDC00004029
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4587697
ChEBI ID132868
PubChem Compound ID5481969
Kegg Compound IDC17867
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12648543
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12662107
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15884809
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15885940
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17396934
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17405024
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18330242
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18608767
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19149258
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21434689
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22145117
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24381530
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24494557
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25981820
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=7903365
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=8435100
17. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.