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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:01:40 UTC
Update Date2022-03-07 02:56:36 UTC
HMDB IDHMDB0040480
Secondary Accession Numbers
  • HMDB40480
Metabolite Identification
Common NameCyclocommunin
DescriptionCyclocommunin 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. Thus, cyclocommunin is considered to be a flavonoid. Cyclocommunin has been detected, but not quantified in, fruits. This could make cyclocommunin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyclocommunin.
Structure
Data?1563863554
Synonyms
ValueSource
IsocyclomulberrinHMDB
Chemical FormulaC25H24O6
Average Molecular Weight420.4545
Monoisotopic Molecular Weight420.1572885
IUPAC Name1,3,8-trihydroxy-2-[(1E)-3-methylbut-1-en-1-yl]-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one
Traditional Namebrosimone I
CAS Registry Number145682-71-9
SMILES
CC(C)\C=C\C1=C(O)C=C2OC3=C(C(OC4=CC(O)=CC=C34)C=C(C)C)C(=O)C2=C1O
InChI Identifier
InChI=1S/C25H24O6/c1-12(2)5-7-15-17(27)11-20-21(23(15)28)24(29)22-19(9-13(3)4)30-18-10-14(26)6-8-16(18)25(22)31-20/h5-12,19,26-28H,1-4H3/b7-5+
InChI KeyAXHZIEAQVMBUKO-FNORWQNLSA-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
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point277 - 279 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP4.86ALOGPS
logP5.46ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.55 m³·mol⁻¹ChemAxon
Polarizability45.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-233.60730932474
DeepCCS[M+Na]+209.0230932474
AllCCS[M+H]+203.732859911
AllCCS[M+H-H2O]+201.032859911
AllCCS[M+NH4]+206.132859911
AllCCS[M+Na]+206.832859911
AllCCS[M-H]-200.832859911
AllCCS[M+Na-2H]-200.632859911
AllCCS[M+HCOO]-200.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclocommuninCC(C)\C=C\C1=C(O)C=C2OC3=C(C(OC4=CC(O)=CC=C34)C=C(C)C)C(=O)C2=C1O5430.0Standard polar33892256
CyclocommuninCC(C)\C=C\C1=C(O)C=C2OC3=C(C(OC4=CC(O)=CC=C34)C=C(C)C)C(=O)C2=C1O3502.3Standard non polar33892256
CyclocommuninCC(C)\C=C\C1=C(O)C=C2OC3=C(C(OC4=CC(O)=CC=C34)C=C(C)C)C(=O)C2=C1O3768.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclocommunin,1TMS,isomer #1CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O[Si](C)(C)C)C=C1O23654.4Semi standard non polar33892256
Cyclocommunin,1TMS,isomer #2CC(C)=CC1OC2=CC(O[Si](C)(C)C)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O)C=C1O23631.6Semi standard non polar33892256
Cyclocommunin,1TMS,isomer #3CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C)C(/C=C/C(C)C)=C(O)C=C1O23627.0Semi standard non polar33892256
Cyclocommunin,2TMS,isomer #1CC(C)=CC1OC2=CC(O[Si](C)(C)C)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O[Si](C)(C)C)C=C1O23589.4Semi standard non polar33892256
Cyclocommunin,2TMS,isomer #2CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C)C(/C=C/C(C)C)=C(O[Si](C)(C)C)C=C1O23594.1Semi standard non polar33892256
Cyclocommunin,2TMS,isomer #3CC(C)=CC1OC2=CC(O[Si](C)(C)C)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C)C(/C=C/C(C)C)=C(O)C=C1O23560.3Semi standard non polar33892256
Cyclocommunin,3TMS,isomer #1CC(C)=CC1OC2=CC(O[Si](C)(C)C)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C)C(/C=C/C(C)C)=C(O[Si](C)(C)C)C=C1O23583.2Semi standard non polar33892256
Cyclocommunin,1TBDMS,isomer #1CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O23897.2Semi standard non polar33892256
Cyclocommunin,1TBDMS,isomer #2CC(C)=CC1OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O)C=C1O23860.3Semi standard non polar33892256
Cyclocommunin,1TBDMS,isomer #3CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(/C=C/C(C)C)=C(O)C=C1O23858.0Semi standard non polar33892256
Cyclocommunin,2TBDMS,isomer #1CC(C)=CC1OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=C1C(=O)C1=C(O)C(/C=C/C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O24073.1Semi standard non polar33892256
Cyclocommunin,2TBDMS,isomer #2CC(C)=CC1OC2=CC(O)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(/C=C/C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O24053.7Semi standard non polar33892256
Cyclocommunin,2TBDMS,isomer #3CC(C)=CC1OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(/C=C/C(C)C)=C(O)C=C1O24006.2Semi standard non polar33892256
Cyclocommunin,3TBDMS,isomer #1CC(C)=CC1OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(/C=C/C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O24203.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclocommunin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-1549600000-813f7a7ae60f9ff2856b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclocommunin GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1100049000-29caa2d8b7580e7bc5762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclocommunin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 10V, Positive-QTOFsplash10-00di-2002900000-a44f7397631e2a2cdf0d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 20V, Positive-QTOFsplash10-0aou-7149300000-f9812e0bcec2c310404f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 40V, Positive-QTOFsplash10-0aor-9000000000-eb63dc3d1688e78cdddf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 10V, Negative-QTOFsplash10-014i-0000900000-94f49230c6693f6214932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 20V, Negative-QTOFsplash10-014i-0006900000-d8195d3552954e0f6f5d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 40V, Negative-QTOFsplash10-0pc0-2937200000-1b8ef5182089d2e434742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 10V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 20V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 40V, Negative-QTOFsplash10-014l-0190200000-a1118abed2e9f1ffe42a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 10V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 20V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclocommunin 40V, Positive-QTOFsplash10-00di-0091500000-610818bebc0b22e7d3032021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020239
KNApSAcK IDC00030075
Chemspider ID8155115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9979523
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1883681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .