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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:38 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030561
Secondary Accession Numbers
  • HMDB30561
Metabolite Identification
Common Name3-Hydroxy-8,9-dimethoxycoumestan
Description3-Hydroxy-8,9-dimethoxycoumestan, also known as alpha-ethyl-3-nitrocinnamic acid, belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, 3-hydroxy-8,9-dimethoxycoumestan is considered to be a flavonoid lipid molecule. 3-Hydroxy-8,9-dimethoxycoumestan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-hydroxy-8,9-dimethoxycoumestan has been detected, but not quantified in, alfalfa and pulses. This could make 3-hydroxy-8,9-dimethoxycoumestan a potential biomarker for the consumption of these foods.
Structure
Data?1563862004
Synonyms
ValueSource
7-Hydroxy-11,12-dimethoxycoumestan (obsol.)HMDB
alpha-Ethyl-3-nitrocinnamic acidHMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Name5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
CAS Registry Number5252-40-4
SMILES
COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3
InChI KeyPKLPURDVDNBFCI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point306 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.5ALOGPS
logP2.39ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.56 m³·mol⁻¹ChemAxon
Polarizability31.6 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]+170.86731661259
DarkChem[M-H]-173.22631661259
DeepCCS[M+H]+177.58230932474
DeepCCS[M-H]-175.22430932474
DeepCCS[M-2H]-209.12230932474
DeepCCS[M+Na]+184.34930932474
AllCCS[M+H]+170.632859911
AllCCS[M+H-H2O]+167.032859911
AllCCS[M+NH4]+173.932859911
AllCCS[M+Na]+174.932859911
AllCCS[M-H]-173.232859911
AllCCS[M+Na-2H]-172.232859911
AllCCS[M+HCOO]-171.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-8,9-dimethoxycoumestanCOC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C14439.5Standard polar33892256
3-Hydroxy-8,9-dimethoxycoumestanCOC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C13068.2Standard non polar33892256
3-Hydroxy-8,9-dimethoxycoumestanCOC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C13203.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-8,9-dimethoxycoumestan,1TMS,isomer #1COC1=CC2=C(C=C1OC)C1=C(O2)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O3162.4Semi standard non polar33892256
3-Hydroxy-8,9-dimethoxycoumestan,1TBDMS,isomer #1COC1=CC2=C(C=C1OC)C1=C(O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O3391.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan GC-MS (Non-derivatized) - 70eV, Positivesplash10-015a-0091000000-02f30903e7d90b5f517c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan GC-MS (1 TMS) - 70eV, Positivesplash10-01dl-2319000000-5cb82e5c9d4f5a71a9752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 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-Hydroxy-8,9-dimethoxycoumestan 10V, Positive-QTOFsplash10-03di-0009000000-7847db498807d288a7452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Positive-QTOFsplash10-03di-0019000000-5e0a950b359893c61d692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Positive-QTOFsplash10-0f8a-0090000000-5378a4a24ae0701e7d172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Negative-QTOFsplash10-03di-0009000000-c2d8b516decd37e8c92e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Negative-QTOFsplash10-03di-0039000000-b23c8cb81c2945a755352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Negative-QTOFsplash10-0a4j-1090000000-1b31caa06e41bc3396ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Positive-QTOFsplash10-03di-0009000000-fbd933023572de11abf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Positive-QTOFsplash10-03di-0009000000-fbd933023572de11abf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Positive-QTOFsplash10-02t9-0092000000-93c3331a462a6af2b2392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Negative-QTOFsplash10-03di-0009000000-b504eaff11e6208b17b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Negative-QTOFsplash10-03di-0069000000-42bdc5bce8039a801f0b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Negative-QTOFsplash10-0f79-0090000000-345260f4d49707f7095e2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002445
KNApSAcK IDC00009768
Chemspider ID4678016
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5748556
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Hydroxy-8,9-dimethoxycoumestan → 6-({13,14-dimethoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails