O-Desmethylangolensin (CHEM002925)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-08-29 04:47:47 UTC
Update Date2016-11-09 01:09:00 UTC
Accession NumberCHEM002925
Identification
Common NameO-Desmethylangolensin
ClassSmall Molecule
DescriptionO-Desmethylangolensin (ODMA) is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism. (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ester
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2',4'-Dihydroxy-2-(P-hydroxyphenyl)-propiophenoneHMDB
2,4-Dihydroxyphenyl P-hydroxyphenethyl ketoneHMDB
O-DemethylangolensinHMDB
O-DemethylangolesinHMDB
O-DesmethylangolensinMeSH
Chemical FormulaC15H14O4
Average Molecular Mass258.269 g/mol
Monoisotopic Mass258.089 g/mol
CAS Registry Number21255-69-6
IUPAC Name1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one
Traditional NameO-desmethylangolensin
SMILESCC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3
InChI KeyJDJPNKPFDDUBFV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAlpha-methyldeoxybenzoin flavonoids
Sub ClassNot Available
Direct ParentAlpha-methyldeoxybenzoin flavonoids
Alternative Parents
Substituents
  • Alpha-methyldeoxybenzoin flavonoid
  • Stilbene
  • Alkyl-phenylketone
  • Phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP2.98ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.7 m³·mol⁻¹ChemAxon
Polarizability26.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-39495ea1c0376894fddfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-4430900000-0e7b58ddbbc19e665858Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-95a81edd733d13d61677Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-1930000000-6a844b2d3f64f75db87bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4900000000-3c4808d490aaff85f058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-1b486ce055fb4c745e83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0490000000-f6b7ddbf92a2c481414bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-6910000000-ef3d7901fc4103baf88dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-c2a50a42dfada53572a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2590000000-ff1a68dd0b89bc03287cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-6900000000-8f8d3654f73a1a919a16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-1ca6275f205a504ebd5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1910000000-a1d96f103a978278101fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-8900000000-a6ac1b1337f1eee505a2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityO-desmethylangolensin (ODMA) exerts androgen receptor antagonistic activity and agonistic activity towards estrogen receptor (ER)-α and ERβ. The structure of ODMA is somewhat similar to estrogen. (3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004629
FooDB IDFDB023387
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkO-Desmethylangolensin
Chemspider ID80750
ChEBI ID88902
PubChem Compound ID89472
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceSalakka, A.; Wahala, K. Synthesis of a-methyldeoxybenzoins. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1999), (18), 2601-2604.
MSDSNot Available
General References
1. Salakka, A.; Wahala, K. Synthesis of a-methyldeoxybenzoins. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1999), (18), 2601-2604.
2. Atkinson C, Newton KM, Bowles EJ, Yong M, Lampe JW: Demographic, anthropometric, and lifestyle factors and dietary intakes in relation to daidzein-metabolizing phenotypes among premenopausal women in the United States. Am J Clin Nutr. 2008 Mar;87(3):679-87.
3. Possemiers S, Bolca S, Eeckhaut E, Depypere H, Verstraete W: Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. FEMS Microbiol Ecol. 2007 Aug;61(2):372-83. Epub 2007 May 16.