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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:01:44 UTC
Update Date2022-03-07 02:56:36 UTC
HMDB IDHMDB0040481
Secondary Accession Numbers
  • HMDB40481
Metabolite Identification
Common NameDihydroisocycloartomunin
DescriptionDihydroisocycloartomunin 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, dihydroisocycloartomunin is considered to be a flavonoid. Dihydroisocycloartomunin has been detected, but not quantified in, breadfruits (Artocarpus altilis) and fruits. This could make dihydroisocycloartomunin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydroisocycloartomunin.
Structure
Data?1563863555
Synonyms
ValueSource
3,8,10-Trihydroxy-2-methoxy-11-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-7-oneHMDB
Chemical FormulaC26H26O7
Average Molecular Weight450.4804
Monoisotopic Molecular Weight450.167853186
IUPAC Name1,3,8-trihydroxy-7-methoxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one
Traditional Namedihydroisocycloartomunin
CAS Registry Number145643-97-6
SMILES
COC1=C(O)C=C2OC(C=C(C)C)C3=C(OC4=C(CC=C(C)C)C(O)=CC(O)=C4C3=O)C2=C1
InChI Identifier
InChI=1S/C26H26O7/c1-12(2)6-7-14-16(27)10-18(29)22-24(30)23-21(8-13(3)4)32-19-11-17(28)20(31-5)9-15(19)26(23)33-25(14)22/h6,8-11,21,27-29H,7H2,1-5H3
InChI KeyJFHXTPDDKBBGNW-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
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point250 - 252 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0028 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.14ALOGPS
logP5.17ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.74 m³·mol⁻¹ChemAxon
Polarizability47.81 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]+211.02230932474
DeepCCS[M-H]-208.66430932474
DeepCCS[M-2H]-241.54930932474
DeepCCS[M+Na]+217.28330932474
AllCCS[M+H]+208.632859911
AllCCS[M+H-H2O]+206.232859911
AllCCS[M+NH4]+210.932859911
AllCCS[M+Na]+211.632859911
AllCCS[M-H]-203.532859911
AllCCS[M+Na-2H]-203.232859911
AllCCS[M+HCOO]-203.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydroisocycloartomuninCOC1=C(O)C=C2OC(C=C(C)C)C3=C(OC4=C(CC=C(C)C)C(O)=CC(O)=C4C3=O)C2=C15948.9Standard polar33892256
DihydroisocycloartomuninCOC1=C(O)C=C2OC(C=C(C)C)C3=C(OC4=C(CC=C(C)C)C(O)=CC(O)=C4C3=O)C2=C13738.2Standard non polar33892256
DihydroisocycloartomuninCOC1=C(O)C=C2OC(C=C(C)C)C3=C(OC4=C(CC=C(C)C)C(O)=CC(O)=C4C3=O)C2=C13904.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroisocycloartomunin,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O3795.4Semi standard non polar33892256
Dihydroisocycloartomunin,1TMS,isomer #2COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O)=C2C1=O3777.2Semi standard non polar33892256
Dihydroisocycloartomunin,1TMS,isomer #3COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C)=C2C1=O3776.5Semi standard non polar33892256
Dihydroisocycloartomunin,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O)=C2C1=O3684.5Semi standard non polar33892256
Dihydroisocycloartomunin,2TMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C)=C2C1=O3690.9Semi standard non polar33892256
Dihydroisocycloartomunin,2TMS,isomer #3COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O3662.5Semi standard non polar33892256
Dihydroisocycloartomunin,3TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O3633.2Semi standard non polar33892256
Dihydroisocycloartomunin,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O4034.8Semi standard non polar33892256
Dihydroisocycloartomunin,1TBDMS,isomer #2COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O3998.3Semi standard non polar33892256
Dihydroisocycloartomunin,1TBDMS,isomer #3COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3997.1Semi standard non polar33892256
Dihydroisocycloartomunin,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O4094.8Semi standard non polar33892256
Dihydroisocycloartomunin,2TBDMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O4112.3Semi standard non polar33892256
Dihydroisocycloartomunin,2TBDMS,isomer #3COC1=CC2=C(C=C1O)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O4077.7Semi standard non polar33892256
Dihydroisocycloartomunin,3TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(C=C(C)C)C1=C2OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O4199.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisocycloartomunin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1143900000-d5083b17a431bf501d492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisocycloartomunin GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1000029000-ddd4a95838ddfa910f562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisocycloartomunin 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 - Dihydroisocycloartomunin 10V, Positive-QTOFsplash10-0udi-1201900000-2d74a9b3cf15dcca0b752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 20V, Positive-QTOFsplash10-00r2-6359800000-3952cdcdd4c2c98c31382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 40V, Positive-QTOFsplash10-0a4i-9200000000-9918d5c36957f1dad1b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 10V, Negative-QTOFsplash10-0002-0000900000-da08b6d1a7b9b768e0ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 20V, Negative-QTOFsplash10-000t-1003900000-08e70cde01151d1f09792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 40V, Negative-QTOFsplash10-057i-3229500000-e270ea49531abce8aaa02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 10V, Positive-QTOFsplash10-0udi-0000900000-30d6dbec2c40cf11fac92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 20V, Positive-QTOFsplash10-0udi-0000900000-30d6dbec2c40cf11fac92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 40V, Positive-QTOFsplash10-0uk9-0092500000-7f220ac864f2d59d8a142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 10V, Negative-QTOFsplash10-0002-0000900000-158c2738b67dc7435f5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 20V, Negative-QTOFsplash10-0002-0000900000-158c2738b67dc7435f5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisocycloartomunin 40V, Negative-QTOFsplash10-00xs-0190200000-e4bd52bf4e1fcc3769562021-09-22Wishart 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 IDFDB020240
KNApSAcK IDC00004103
Chemspider ID8270829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10095293
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1883691
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.. .