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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:13:15 UTC
Update Date2022-03-07 02:55:58 UTC
HMDB IDHMDB0038872
Secondary Accession Numbers
  • HMDB38872
Metabolite Identification
Common NameErybraedin A
DescriptionErybraedin A belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, erybraedin a is considered to be a flavonoid. Erybraedin A has been detected, but not quantified in, lima beans (Phaseolus lunatus) and pulses. This could make erybraedin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Erybraedin A.
Structure
Data?1563863273
Synonyms
ValueSource
(6AR,11ar)-3,9-dihydroxy-4,10-diprenylpterocarpanHMDB
4-PrenylphaseollidinHMDB
6a,11a-dihydro-4,10-Bis(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 9ciHMDB
Chemical FormulaC25H28O4
Average Molecular Weight392.4874
Monoisotopic Molecular Weight392.198759384
IUPAC Name6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol
Traditional Nameerybraedin A
CAS Registry Number119269-76-0
SMILES
CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=C(C)C
InChI Identifier
InChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3
InChI KeyHOGHBEDTLGAJAS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Coumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen 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 Point69 - 71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0057 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP5.24ALOGPS
logP5.82ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.06 m³·mol⁻¹ChemAxon
Polarizability44.68 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
DarkChem[M+H]+196.14231661259
DarkChem[M-H]-190.06231661259
DeepCCS[M+H]+190.77130932474
DeepCCS[M-H]-188.41230932474
DeepCCS[M-2H]-222.78430932474
DeepCCS[M+Na]+197.93230932474
AllCCS[M+H]+200.732859911
AllCCS[M+H-H2O]+197.932859911
AllCCS[M+NH4]+203.232859911
AllCCS[M+Na]+204.032859911
AllCCS[M-H]-197.732859911
AllCCS[M+Na-2H]-197.632859911
AllCCS[M+HCOO]-197.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Erybraedin ACC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=C(C)C4325.7Standard polar33892256
Erybraedin ACC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=C(C)C3197.2Standard non polar33892256
Erybraedin ACC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=C(C)C3372.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Erybraedin A,1TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O)C(CC=C(C)C)=C3OCC213208.6Semi standard non polar33892256
Erybraedin A,1TMS,isomer #2CC(C)=CCC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OCC213223.8Semi standard non polar33892256
Erybraedin A,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OCC213187.8Semi standard non polar33892256
Erybraedin A,1TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O)C(CC=C(C)C)=C3OCC213421.8Semi standard non polar33892256
Erybraedin A,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OCC213433.0Semi standard non polar33892256
Erybraedin A,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OCC213567.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Erybraedin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbl-2019000000-8d6646c9515462c949112017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erybraedin A GC-MS (2 TMS) - 70eV, Positivesplash10-00di-2010590000-7046869a7ecebbe977e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erybraedin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erybraedin A 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 - Erybraedin A 10V, Negative-QTOFsplash10-0006-0009000000-3fb281e63bf5492ae9912016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 20V, Negative-QTOFsplash10-0006-0029000000-48e4c09ac77b7e4de95e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 40V, Negative-QTOFsplash10-0kvn-1963000000-d7f643af91d736e8c7482016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 10V, Negative-QTOFsplash10-0006-0009000000-fc8307e58aa68e585da32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 20V, Negative-QTOFsplash10-0006-0009000000-997ebd62918a554881832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 40V, Negative-QTOFsplash10-0ac1-1459000000-7dca22307b0bf19f95eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 10V, Positive-QTOFsplash10-002f-0609000000-7f6eafcd3573353ef49d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 20V, Positive-QTOFsplash10-004r-2629000000-98dd261731516b0f25922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 40V, Positive-QTOFsplash10-07vi-5910000000-4ba38f879f50af3d25ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 10V, Positive-QTOFsplash10-0006-0019000000-f4d93cb7f6a975b807aa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 20V, Positive-QTOFsplash10-00o9-0094000000-58223063196c6f79ddcd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erybraedin A 40V, Positive-QTOFsplash10-004l-3894000000-ed0f2dbfd6f04605cf7e2021-09-23Wishart 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 IDFDB018318
KNApSAcK IDC00010016
Chemspider ID321822
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound362562
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1872231
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.. .