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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:25 UTC
Update Date2022-03-07 02:52:39 UTC
HMDB IDHMDB0030685
Secondary Accession Numbers
  • HMDB30685
Metabolite Identification
Common NameCycloheterophyllin
DescriptionCycloheterophyllin 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, cycloheterophyllin is considered to be a flavonoid. Cycloheterophyllin has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make cycloheterophyllin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cycloheterophyllin.
Structure
Data?1563862022
Synonyms
ValueSource
2,3,8-Trihydroxy-11,11-dimethyl-13-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H,11H-bis[1]benzopyrano[4,3-b:6',7'-e]pyran-7-one, 9ciHMDB
Chemical FormulaC30H30O7
Average Molecular Weight502.555
Monoisotopic Molecular Weight502.199153314
IUPAC Name6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one
Traditional Namecycloheterophyllin
CAS Registry Number36545-53-6
SMILES
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O
InChI Identifier
InChI=1S/C30H30O7/c1-14(2)7-8-17-27-16(9-10-30(5,6)37-27)25(33)24-26(34)23-22(11-15(3)4)35-21-13-20(32)19(31)12-18(21)29(23)36-28(17)24/h7,9-13,22,31-33H,8H2,1-6H3
InChI KeyZZPIXEJZTXAVCX-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
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Point205 - 206 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0036 g/LALOGPS
logP5.18ALOGPS
logP6.23ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity144.67 m³·mol⁻¹ChemAxon
Polarizability55.48 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+219.15531661259
DarkChem[M-H]-215.91231661259
DeepCCS[M+H]+219.48730932474
DeepCCS[M-H]-217.09130932474
DeepCCS[M-2H]-249.97730932474
DeepCCS[M+Na]+225.430932474
AllCCS[M+H]+220.432859911
AllCCS[M+H-H2O]+218.332859911
AllCCS[M+NH4]+222.332859911
AllCCS[M+Na]+222.832859911
AllCCS[M-H]-212.732859911
AllCCS[M+Na-2H]-212.932859911
AllCCS[M+HCOO]-213.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CycloheterophyllinCC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O5525.5Standard polar33892256
CycloheterophyllinCC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O4284.7Standard non polar33892256
CycloheterophyllinCC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O4137.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloheterophyllin,1TMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O)C=C213931.7Semi standard non polar33892256
Cycloheterophyllin,1TMS,isomer #2CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C)C=C213938.6Semi standard non polar33892256
Cycloheterophyllin,1TMS,isomer #3CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O)C=C213952.8Semi standard non polar33892256
Cycloheterophyllin,2TMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C)C=C213832.5Semi standard non polar33892256
Cycloheterophyllin,2TMS,isomer #2CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O)C=C213852.6Semi standard non polar33892256
Cycloheterophyllin,2TMS,isomer #3CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C213875.9Semi standard non polar33892256
Cycloheterophyllin,3TMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C213804.9Semi standard non polar33892256
Cycloheterophyllin,1TBDMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O)C=C214165.2Semi standard non polar33892256
Cycloheterophyllin,1TBDMS,isomer #2CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C214173.8Semi standard non polar33892256
Cycloheterophyllin,1TBDMS,isomer #3CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C214189.8Semi standard non polar33892256
Cycloheterophyllin,2TBDMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C214230.7Semi standard non polar33892256
Cycloheterophyllin,2TBDMS,isomer #2CC(C)=CCC1=C2OC(C)(C)C=CC2=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)=C(O)C=C214249.7Semi standard non polar33892256
Cycloheterophyllin,2TBDMS,isomer #3CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C214280.0Semi standard non polar33892256
Cycloheterophyllin,3TBDMS,isomer #1CC(C)=CCC1=C2OC(C)(C)C=CC2=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)=C(O[Si](C)(C)C(C)(C)C)C=C214346.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cycloheterophyllin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1210900000-2b9348571f9c2ede2c212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloheterophyllin GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2100029000-1a10b698dc6f89f727b52017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Positive-QTOFsplash10-0udi-1301890000-3a9668040559528c86dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Positive-QTOFsplash10-07bb-3103910000-3e34e7b9d27e80266f152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Positive-QTOFsplash10-0pxr-9501100000-7f051663aa9661ab06112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Negative-QTOFsplash10-0udi-0000190000-684986bbcc1af6b7bb2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Negative-QTOFsplash10-0udi-1002960000-ab6c73fca49f7aae21e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Negative-QTOFsplash10-0apj-1445900000-e6a2476407cfa534cc222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Negative-QTOFsplash10-0udi-0000090000-27a32bd6c97a965edc442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Negative-QTOFsplash10-0udi-0000090000-27a32bd6c97a965edc442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Negative-QTOFsplash10-0a4r-0090010000-7e9d5fac0bdd16aa06132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Positive-QTOFsplash10-0udi-0000090000-db49500cd3a1fa6367862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Positive-QTOFsplash10-0udi-0000090000-db49500cd3a1fa6367862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Positive-QTOFsplash10-0f79-0090250000-7dd066fbdb79c38212a82021-09-22Wishart 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 IDFDB002604
KNApSAcK IDC00004064
Chemspider ID4475345
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5316250
PDB IDNot Available
ChEBI ID563917
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. Lin CN, Lu CM, Lin HC, Fang SC, Shieh BJ, Hsu MF, Wang JP, Ko FN, Teng CM: Novel antiplatelet constituents from formosan moraceous plants. J Nat Prod. 1996 Sep;59(9):834-8. [PubMed:8864236 ]
  2. (). 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
Cycloheterophyllin → 6-{[6,15-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4,6,8,15,17,21-octaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Cycloheterophyllin → 6-{[7,15-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4,6,8,15,17,21-octaen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Cycloheterophyllin → 6-{[6,7-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-15-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails