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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:33:59 UTC
Update Date2022-03-07 02:57:06 UTC
HMDB IDHMDB0041647
Secondary Accession Numbers
  • HMDB41647
Metabolite Identification
Common Name2-Dehydro-O-desmethylangolensin
Description2-Dehydro-O-desmethylangolensin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on 2-Dehydro-O-desmethylangolensin.
Structure
Data?1563863687
SynonymsNot Available
Chemical FormulaC15H12O4
Average Molecular Weight256.2534
Monoisotopic Molecular Weight256.073558872
IUPAC Name1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Name1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C15H12O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-8,16-18H,1H2
InChI KeyMPNKZWIUITZJCR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Benzoyl
  • Resorcinol
  • Aryl ketone
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP2.98ALOGPS
logP3.69ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.72ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.5 m³·mol⁻¹ChemAxon
Polarizability25.81 ųChemAxon
Number of Rings2ChemAxon
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]+161.34131661259
DarkChem[M-H]-161.65131661259
DeepCCS[M+H]+165.1430932474
DeepCCS[M-H]-162.78230932474
DeepCCS[M-2H]-195.66830932474
DeepCCS[M+Na]+171.23330932474
AllCCS[M+H]+158.432859911
AllCCS[M+H-H2O]+154.432859911
AllCCS[M+NH4]+162.232859911
AllCCS[M+Na]+163.232859911
AllCCS[M-H]-158.032859911
AllCCS[M+Na-2H]-157.532859911
AllCCS[M+HCOO]-157.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Dehydro-O-desmethylangolensinOC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C14242.3Standard polar33892256
2-Dehydro-O-desmethylangolensinOC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C12451.5Standard non polar33892256
2-Dehydro-O-desmethylangolensinOC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C12776.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Dehydro-O-desmethylangolensin,1TMS,isomer #1C=C(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C12570.6Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,1TMS,isomer #2C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C12568.9Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,1TMS,isomer #3C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O)C=C12587.3Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #1C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C12579.1Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #2C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C12544.0Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #3C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C12554.4Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,3TMS,isomer #1C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C12615.5Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #1C=C(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12863.0Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #2C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C12878.8Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #3C=C(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C1=CC=C(O)C=C12877.9Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #1C=C(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13133.4Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #2C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13099.9Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #3C=C(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C13092.3Semi standard non polar33892256
2-Dehydro-O-desmethylangolensin,3TBDMS,isomer #1C=C(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13379.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dehydro-O-desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-5930000000-61e0a06d5028cd69d8192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dehydro-O-desmethylangolensin GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-5413900000-b940d94fbc562b19d3fe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dehydro-O-desmethylangolensin 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 - 2-Dehydro-O-desmethylangolensin 10V, Positive-QTOFsplash10-0a4i-0390000000-8dd26699daaf59809aa02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Positive-QTOFsplash10-000b-1930000000-84edc7ed490a9c3144142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Positive-QTOFsplash10-014i-3900000000-a49f5e11700e329c23a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Negative-QTOFsplash10-0a4i-0190000000-870ea4f7f70c26afdf422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Negative-QTOFsplash10-0a4i-0390000000-f0cb33dbf2aa4f601e2f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Negative-QTOFsplash10-0aor-7900000000-33263f5dadb41e9bf42d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Negative-QTOFsplash10-0a4i-0190000000-838a14b5d4c546b0c3372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Negative-QTOFsplash10-0ap0-0940000000-4825b3dae808a4b2a5a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Negative-QTOFsplash10-014i-9400000000-6cc94137def3608423d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Positive-QTOFsplash10-0a4i-0290000000-99086cfea20d711030d22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Positive-QTOFsplash10-014r-0900000000-d81b7b4a231fdb21d0fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Positive-QTOFsplash10-0fvl-9600000000-c6b777fc3a0af7a126e22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 826 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 826 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029802
KNApSAcK IDNot Available
Chemspider ID8396211
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10220719
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. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

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
2-Dehydro-O-desmethylangolensin → 6-{4-[3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Dehydro-O-desmethylangolensin → 3,4,5-trihydroxy-6-{3-hydroxy-4-[2-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}oxane-2-carboxylic aciddetails
2-Dehydro-O-desmethylangolensin → 3,4,5-trihydroxy-6-{5-hydroxy-2-[2-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-Dehydro-O-desmethylangolensin → {4-[3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-2-yl]phenyl}oxidanesulfonic aciddetails