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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:26 UTC
Update Date2022-03-07 02:52:39 UTC
HMDB IDHMDB0030688
Secondary Accession Numbers
  • HMDB30688
Metabolite Identification
Common NameCyclomulberrin
DescriptionCyclomulberrin 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, cyclomulberrin is considered to be a flavonoid. Cyclomulberrin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Cyclomulberrin.
Structure
Data?1563862022
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 Weight420.4545
Monoisotopic Molecular Weight420.1572885
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
CAS Registry Number19275-51-5
SMILES
CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point245 - 246 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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+H]+202.07830932474
DeepCCS[M-H]-199.68230932474
DeepCCS[M-2H]-232.83730932474
DeepCCS[M+Na]+208.12930932474
AllCCS[M+H]+202.432859911
AllCCS[M+H-H2O]+199.732859911
AllCCS[M+NH4]+204.832859911
AllCCS[M+Na]+205.532859911
AllCCS[M-H]-197.032859911
AllCCS[M+Na-2H]-196.532859911
AllCCS[M+HCOO]-196.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclomulberrinCC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O5549.4Standard polar33892256
CyclomulberrinCC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O3707.3Standard non polar33892256
CyclomulberrinCC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O3792.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclomulberrin,1TMS,isomer #1CC(C)=CCC1=C(O)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C213695.6Semi standard non polar33892256
Cyclomulberrin,1TMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213666.3Semi standard non polar33892256
Cyclomulberrin,1TMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213666.2Semi standard non polar33892256
Cyclomulberrin,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C213595.2Semi standard non polar33892256
Cyclomulberrin,2TMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C213612.7Semi standard non polar33892256
Cyclomulberrin,2TMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213552.1Semi standard non polar33892256
Cyclomulberrin,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C213553.9Semi standard non polar33892256
Cyclomulberrin,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213929.6Semi standard non polar33892256
Cyclomulberrin,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213897.7Semi standard non polar33892256
Cyclomulberrin,1TBDMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213891.0Semi standard non polar33892256
Cyclomulberrin,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C214028.5Semi standard non polar33892256
Cyclomulberrin,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C214060.4Semi standard non polar33892256
Cyclomulberrin,2TBDMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C213986.9Semi standard non polar33892256
Cyclomulberrin,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C214142.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomulberrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-3449500000-b0c4f508485b909ccc202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomulberrin GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2000049000-7bc0dfe9b13feece76ff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomulberrin 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 - Cyclomulberrin 10V, Positive-QTOFsplash10-00di-1003900000-a8a0b37cb5840caad0e42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Positive-QTOFsplash10-014i-3149300000-e243ed99e4d684dc3c972016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Positive-QTOFsplash10-014i-9110100000-503470b143240bb8e9a72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Negative-QTOFsplash10-014i-0000900000-006a3fbd24235bcbecdc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Negative-QTOFsplash10-014i-0106900000-8d01ab175ce87619c15f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Negative-QTOFsplash10-0pdi-3915100000-bf6aaab044167770d1832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Negative-QTOFsplash10-014l-0190200000-a1118abed2e9f1ffe42a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Positive-QTOFsplash10-00di-0091500000-3ae896b8f74c53ff643a2021-09-22Wishart 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 IDFDB002607
KNApSAcK IDC00004061
Chemspider ID9917576
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11742872
PDB IDNot Available
ChEBI ID132869
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Cyclomulberrin → 6-{[1,8-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Cyclomulberrin → 6-{[3,8-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Cyclomulberrin → 6-{[1,3-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails