Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:29:31 UTC
Update Date2022-03-07 02:55:15 UTC
HMDB IDHMDB0037252
Secondary Accession Numbers
  • HMDB37252
Metabolite Identification
Common Name5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate
Description5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate has been detected, but not quantified in, herbs and spices. This could make 5,8-dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate.
Structure
Data?1563863000
Synonyms
ValueSource
5-Hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl acetic acidHMDB
Chemical FormulaC19H18O7
Average Molecular Weight358.342
Monoisotopic Molecular Weight358.10525293
IUPAC Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl acetate
Traditional Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-8-yl acetate
CAS Registry Number99877-75-5
SMILES
COC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2
InChI Identifier
InChI=1S/C19H18O7/c1-10(20)26-18-15(24-2)8-14(22)16-17(23)12(9-25-19(16)18)7-11-3-5-13(21)6-4-11/h3-6,8,12,21-22H,7,9H2,1-2H3
InChI KeyNXGGYXKVAVMQLL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavans
Direct ParentHomoisoflavanones
Alternative Parents
Substituents
  • Homoisoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point155 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.12ALOGPS
logP2.93ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.89 m³·mol⁻¹ChemAxon
Polarizability35.66 ųChemAxon
Number of Rings3ChemAxon
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]+184.04631661259
DarkChem[M-H]-181.61731661259
DeepCCS[M+H]+179.62930932474
DeepCCS[M-H]-177.27130932474
DeepCCS[M-2H]-211.39330932474
DeepCCS[M+Na]+186.62130932474
AllCCS[M+H]+184.032859911
AllCCS[M+H-H2O]+180.932859911
AllCCS[M+NH4]+186.932859911
AllCCS[M+Na]+187.832859911
AllCCS[M-H]-185.932859911
AllCCS[M+Na-2H]-185.832859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetateCOC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO24146.8Standard polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetateCOC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO23084.5Standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetateCOC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO23173.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC(C)=O2969.2Semi standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,1TMS,isomer #2COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC(C)=O2969.9Semi standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC(C)=O2997.1Semi standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC(C)=O3188.7Semi standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC(C)=O3191.8Semi standard non polar33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC(C)=O3457.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-1419000000-b0ecf8a1f92634443b592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate GC-MS (2 TMS) - 70eV, Positivesplash10-054w-4300900000-aa72cd4374b7c15736bb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 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 - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 10V, Positive-QTOFsplash10-0a4i-0249000000-7aea38e5e85b74b335d02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 20V, Positive-QTOFsplash10-0ar0-0965000000-63c8850b7c91af7500932016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 40V, Positive-QTOFsplash10-053r-1910000000-4c71e9a133fac5f16c4f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 10V, Negative-QTOFsplash10-0a4i-1129000000-a88901a1764bac53a9842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 20V, Negative-QTOFsplash10-0a4i-6297000000-4ae5e6abc49e76f6de7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 40V, Negative-QTOFsplash10-0a4l-9240000000-d06977ddba9aa7418f302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 10V, Negative-QTOFsplash10-0a4i-0009000000-f52033267e0ba5a1ec2d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 20V, Negative-QTOFsplash10-0a4i-1139000000-663887bbcfe571c493b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 40V, Negative-QTOFsplash10-0a4m-9565000000-a1ece6368b8f7f03e89f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 10V, Positive-QTOFsplash10-0a4i-0009000000-eed93a82077af8513ad12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 20V, Positive-QTOFsplash10-0aor-0119000000-41c4a0823ae13f770b682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate 40V, Positive-QTOFsplash10-0a4l-2952000000-a3ee8a989d2d27bddb942021-09-22Wishart 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 IDFDB016263
KNApSAcK IDNot Available
Chemspider ID10254761
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21627907
PDB IDNot Available
ChEBI ID168807
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.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate → 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanonedetails