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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:36 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033936
Secondary Accession Numbers
  • HMDB33936
Metabolite Identification
Common Name3,3'-Bisjuglone
Description3,3'-Bisjuglone belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 3,3'-Bisjuglone has been detected, but not quantified in, nuts. This could make 3,3'-bisjuglone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Bisjuglone.
Structure
Data?1563862484
Synonyms
ValueSource
3,3'-BijugloneHMDB
8,8'-Dihydroxy[2,2'-binaphthalene]-1,1',4,4'-tetrone, 9ciHMDB
Chemical FormulaC20H10O6
Average Molecular Weight346.2898
Monoisotopic Molecular Weight346.047738052
IUPAC Name8-hydroxy-2-(8-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1,4-dihydronaphthalene-1,4-dione
Traditional Name8-hydroxy-2-(8-hydroxy-1,4-dioxonaphthalen-2-yl)naphthalene-1,4-dione
CAS Registry Number61836-43-9
SMILES
OC1=CC=CC2=C1C(=O)C(=CC2=O)C1=CC(=O)C2=C(C(O)=CC=C2)C1=O
InChI Identifier
InChI=1S/C20H10O6/c21-13-5-1-3-9-15(23)7-11(19(25)17(9)13)12-8-16(24)10-4-2-6-14(22)18(10)20(12)26/h1-8,21-22H
InChI KeyYSWLZVWSHJYBPI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP3.45ALOGPS
logP3.12ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.74 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.04 m³·mol⁻¹ChemAxon
Polarizability33.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.05831661259
DarkChem[M-H]-180.61631661259
DeepCCS[M+H]+175.0830932474
DeepCCS[M-H]-172.72230932474
DeepCCS[M-2H]-206.63130932474
DeepCCS[M+Na]+181.85930932474
AllCCS[M+H]+180.732859911
AllCCS[M+H-H2O]+177.432859911
AllCCS[M+NH4]+183.832859911
AllCCS[M+Na]+184.732859911
AllCCS[M-H]-180.932859911
AllCCS[M+Na-2H]-180.132859911
AllCCS[M+HCOO]-179.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,3'-BisjugloneOC1=CC=CC2=C1C(=O)C(=CC2=O)C1=CC(=O)C2=C(C(O)=CC=C2)C1=O4647.2Standard polar33892256
3,3'-BisjugloneOC1=CC=CC2=C1C(=O)C(=CC2=O)C1=CC(=O)C2=C(C(O)=CC=C2)C1=O2558.0Standard non polar33892256
3,3'-BisjugloneOC1=CC=CC2=C1C(=O)C(=CC2=O)C1=CC(=O)C2=C(C(O)=CC=C2)C1=O3435.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,3'-Bisjuglone,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1C(=O)C(C1=CC(=O)C3=CC=CC(O)=C3C1=O)=CC2=O3515.9Semi standard non polar33892256
3,3'-Bisjuglone,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1C(=O)C(C1=CC(=O)C3=CC=CC(O[Si](C)(C)C)=C3C1=O)=CC2=O3490.4Semi standard non polar33892256
3,3'-Bisjuglone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C(C1=CC(=O)C3=CC=CC(O)=C3C1=O)=CC2=O3766.8Semi standard non polar33892256
3,3'-Bisjuglone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C(C1=CC(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)=CC2=O3982.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,3'-Bisjuglone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-0329000000-1cf615797359700a86552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3'-Bisjuglone GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6301900000-057cfbe905d8cc60ca1a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3'-Bisjuglone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3'-Bisjuglone 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 - 3,3'-Bisjuglone 10V, Positive-QTOFsplash10-0002-0009000000-80cafe5ec9a03b4413682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 20V, Positive-QTOFsplash10-0002-0639000000-d2ab90dfc122053857da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 40V, Positive-QTOFsplash10-0092-6922000000-6092563433664f2b9dee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 10V, Negative-QTOFsplash10-0002-0009000000-c79cb51d2007fabfbe2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 20V, Negative-QTOFsplash10-0002-0009000000-aee9884ab966426561e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 40V, Negative-QTOFsplash10-0002-5619000000-2267aa9354830ef73db32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 10V, Negative-QTOFsplash10-0002-0009000000-bdb4775e307fe8a890fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 20V, Negative-QTOFsplash10-0002-0009000000-bdb4775e307fe8a890fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 40V, Negative-QTOFsplash10-0170-0096000000-27adfa07c56b95e30de12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 10V, Positive-QTOFsplash10-0002-0009000000-b7ef64c959da91cf98412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 20V, Positive-QTOFsplash10-0002-0009000000-b7ef64c959da91cf98412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Bisjuglone 40V, Positive-QTOFsplash10-0002-0913000000-52c772049a8731305c642021-09-24Wishart 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 IDFDB012142
KNApSAcK IDC00054155
Chemspider ID291952
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound329584
PDB IDNot Available
ChEBI IDNot Available
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.. .