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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:36:44 UTC
Update Date2022-03-07 02:54:12 UTC
HMDB IDHMDB0034709
Secondary Accession Numbers
  • HMDB34709
Metabolite Identification
Common NameBL IV
DescriptionBL IV belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan. BL IV has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make BL IV a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on BL IV.
Structure
Data?1563862607
Synonyms
ValueSource
Cibacron blueHMDB
Cibacron blue 3gaHMDB
Cibacron blue F 3gaHMDB
Reactive blue 2HMDB
3,4-Bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-6-yl acetic acidGenerator
Chemical FormulaC24H18O10
Average Molecular Weight466.3937
Monoisotopic Molecular Weight466.089996796
IUPAC Name4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate
Traditional Name4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate
CAS Registry Number112209-53-7
SMILES
CC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C24H18O10/c1-10(25)31-21-19(13-4-6-14(28)7-5-13)22(32-11(2)26)24-20(23(21)33-12(3)27)15-8-16(29)17(30)9-18(15)34-24/h4-9,28-30H,1-3H3
InChI KeyDTOIFOOSMQSUBD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassPhenylbenzofurans
Direct ParentPhenylbenzofurans
Alternative Parents
Substituents
  • Phenylbenzofuran
  • Dibenzofuran
  • Tricarboxylic acid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point242 - 245 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.085 g/LALOGPS
logP3.96ALOGPS
logP2.71ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area152.73 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity115.7 m³·mol⁻¹ChemAxon
Polarizability46.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.05831661259
DarkChem[M-H]-201.91231661259
DeepCCS[M+H]+198.35730932474
DeepCCS[M-H]-195.96230932474
DeepCCS[M-2H]-228.84530932474
DeepCCS[M+Na]+204.2730932474
AllCCS[M+H]+207.732859911
AllCCS[M+H-H2O]+205.232859911
AllCCS[M+NH4]+209.932859911
AllCCS[M+Na]+210.532859911
AllCCS[M-H]-207.532859911
AllCCS[M+Na-2H]-207.532859911
AllCCS[M+HCOO]-207.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BL IVCC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C15385.8Standard polar33892256
BL IVCC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C13637.7Standard non polar33892256
BL IVCC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C13872.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
BL IV,1TMS,isomer #1CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O[Si](C)(C)C)C=C3C2=C1OC(C)=O3716.1Semi standard non polar33892256
BL IV,1TMS,isomer #2CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C)=C(O)C=C3C2=C1OC(C)=O3710.1Semi standard non polar33892256
BL IV,1TMS,isomer #3CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O)C=C3C2=C1OC(C)=O3684.9Semi standard non polar33892256
BL IV,2TMS,isomer #1CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O[Si](C)(C)C)C=C3C2=C1OC(C)=O3793.4Semi standard non polar33892256
BL IV,2TMS,isomer #2CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3C2=C1OC(C)=O3677.6Semi standard non polar33892256
BL IV,2TMS,isomer #3CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C)=C(O)C=C3C2=C1OC(C)=O3784.4Semi standard non polar33892256
BL IV,3TMS,isomer #1CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3C2=C1OC(C)=O3777.5Semi standard non polar33892256
BL IV,1TBDMS,isomer #1CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3C2=C1OC(C)=O3935.8Semi standard non polar33892256
BL IV,1TBDMS,isomer #2CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3C2=C1OC(C)=O3927.1Semi standard non polar33892256
BL IV,1TBDMS,isomer #3CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O)C=C3C2=C1OC(C)=O3881.7Semi standard non polar33892256
BL IV,2TBDMS,isomer #1CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3C2=C1OC(C)=O4162.2Semi standard non polar33892256
BL IV,2TBDMS,isomer #2CC(=O)OC1=C(C2=CC=C(O)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3C2=C1OC(C)=O4023.4Semi standard non polar33892256
BL IV,2TBDMS,isomer #3CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3C2=C1OC(C)=O4173.2Semi standard non polar33892256
BL IV,3TBDMS,isomer #1CC(=O)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(OC(C)=O)=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3C2=C1OC(C)=O4292.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - BL IV GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-3009700000-5ca5ab890ffa7e5f8b3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - BL IV GC-MS (3 TMS) - 70eV, Positivesplash10-004i-2000029000-9c72e0defb05b22362d02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - BL IV 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 - BL IV 10V, Positive-QTOFsplash10-0690-0002900000-500061fcdf1492f3c9852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 20V, Positive-QTOFsplash10-0arr-0007900000-5f6af351206d97f184ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 40V, Positive-QTOFsplash10-014i-1009200000-a9c0129eaa17ca1c95f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 10V, Negative-QTOFsplash10-00xr-1000900000-bc6c4905f88e2235dcb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 20V, Negative-QTOFsplash10-074i-3005900000-db14893628bde41dcc662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 40V, Negative-QTOFsplash10-0a6r-9008200000-2d9d303a5638d5cc00c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 10V, Negative-QTOFsplash10-014i-0000900000-54d30a3a87379185fc802021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 20V, Negative-QTOFsplash10-0100-0008900000-e2f4b2ca9bcfba3ed73b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 40V, Negative-QTOFsplash10-03fr-0009000000-1ab8f62514ef3b8ba2f42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 10V, Positive-QTOFsplash10-003r-0009400000-ab75d0b64cde7351a3202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 20V, Positive-QTOFsplash10-001i-0009300000-abf1e1dee1d4b07866d92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - BL IV 40V, Positive-QTOFsplash10-03e9-0009200000-b91da9ce65ebd10d91e62021-09-25Wishart 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 IDFDB013244
KNApSAcK IDC00054654
Chemspider ID8519912
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound628742
PDB IDNot Available
ChEBI ID168773
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.. .