Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:49:31 UTC
Update Date2022-03-07 02:56:54 UTC
HMDB IDHMDB0041166
Secondary Accession Numbers
  • HMDB41166
Metabolite Identification
Common NameCycloartocarpin
DescriptionCycloartocarpin 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, cycloartocarpin is considered to be a flavonoid. Cycloartocarpin has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make cycloartocarpin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cycloartocarpin.
Structure
Data?1563863632
Synonyms
ValueSource
Cycloartocarpin aHMDB
Cycloartocarpin?HMDB
Chemical FormulaC26H26O6
Average Molecular Weight434.481
Monoisotopic Molecular Weight434.172938564
IUPAC Name1,3-dihydroxy-8-methoxy-2-[(1E)-3-methylbut-1-en-1-yl]-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one
Traditional Namecycloartocarpin A
CAS Registry Number156127-37-6
SMILES
COC1=CC2=C(C=C1)C1=C(C(O2)C=C(C)C)C(=O)C2=C(O1)C=C(O)C(\C=C\C(C)C)=C2O
InChI Identifier
InChI=1S/C26H26O6/c1-13(2)6-8-16-18(27)12-21-22(24(16)28)25(29)23-20(10-14(3)4)31-19-11-15(30-5)7-9-17(19)26(23)32-21/h6-13,20,27-28H,1-5H3/b8-6+
InChI KeyFUOITKFXHPXSCA-SOFGYWHQSA-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
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen 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 Point262 - 264 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0027 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP4.84ALOGPS
logP5.6ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)6.52ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.03 m³·mol⁻¹ChemAxon
Polarizability48.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+210.18430932474
DeepCCS[M-H]-207.78830932474
DeepCCS[M-2H]-240.67230932474
DeepCCS[M+Na]+216.09630932474
AllCCS[M+H]+207.832859911
AllCCS[M+H-H2O]+205.332859911
AllCCS[M+NH4]+210.132859911
AllCCS[M+Na]+210.832859911
AllCCS[M-H]-205.532859911
AllCCS[M+Na-2H]-205.732859911
AllCCS[M+HCOO]-206.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CycloartocarpinCOC1=CC2=C(C=C1)C1=C(C(O2)C=C(C)C)C(=O)C2=C(O1)C=C(O)C(\C=C\C(C)C)=C2O5189.2Standard polar33892256
CycloartocarpinCOC1=CC2=C(C=C1)C1=C(C(O2)C=C(C)C)C(=O)C2=C(O1)C=C(O)C(\C=C\C(C)C)=C2O3707.8Standard non polar33892256
CycloartocarpinCOC1=CC2=C(C=C1)C1=C(C(O2)C=C(C)C)C(=O)C2=C(O1)C=C(O)C(\C=C\C(C)C)=C2O3695.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloartocarpin,1TMS,isomer #1COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O[Si](C)(C)C)=C(/C=C/C(C)C)C(O)=C2C1=O3669.6Semi standard non polar33892256
Cycloartocarpin,1TMS,isomer #2COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O)=C(/C=C/C(C)C)C(O[Si](C)(C)C)=C2C1=O3660.5Semi standard non polar33892256
Cycloartocarpin,2TMS,isomer #1COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O[Si](C)(C)C)=C(/C=C/C(C)C)C(O[Si](C)(C)C)=C2C1=O3628.2Semi standard non polar33892256
Cycloartocarpin,1TBDMS,isomer #1COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=C(/C=C/C(C)C)C(O)=C2C1=O3913.7Semi standard non polar33892256
Cycloartocarpin,1TBDMS,isomer #2COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O)=C(/C=C/C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3872.4Semi standard non polar33892256
Cycloartocarpin,2TBDMS,isomer #1COC1=CC=C2C(=C1)OC(C=C(C)C)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=C(/C=C/C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4056.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartocarpin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bc-1334900000-af86f66feacbd8364dc82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartocarpin GC-MS (2 TMS) - 70eV, Positivesplash10-03di-1200190000-83728727bca3d647a76f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartocarpin 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 - Cycloartocarpin 10V, Positive-QTOFsplash10-000i-1203900000-262faa1f1b715d2d68e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 20V, Positive-QTOFsplash10-05r9-5249400000-32185aa8ace58c1ce7922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 40V, Positive-QTOFsplash10-0a4i-9200000000-f7042b9c8991441f785f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 10V, Negative-QTOFsplash10-001i-0000900000-ba069a4b889137ac19532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 20V, Negative-QTOFsplash10-00lr-1006900000-ec5f59cb79c1c08b0ea22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 40V, Negative-QTOFsplash10-0699-3829300000-51fef793be23ecde6ec32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 10V, Positive-QTOFsplash10-000i-0000900000-ab4cb610ea14113e774e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 20V, Positive-QTOFsplash10-000i-0000900000-ab4cb610ea14113e774e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 40V, Positive-QTOFsplash10-00dr-0090600000-f2813e64754a9d9aff442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 10V, Negative-QTOFsplash10-001i-0000900000-1ca6fd408646df5f74602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 20V, Negative-QTOFsplash10-001i-0000900000-1ca6fd408646df5f74602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartocarpin 40V, Negative-QTOFsplash10-0api-0190200000-e83e9e9363cb36ed60072021-09-24Wishart 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 IDFDB021056
KNApSAcK IDC00004101
Chemspider ID23339465
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258302
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1890141
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.. .