Showing metabocard for Enterodiol (BMDB0005056)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:07 UTC
Update Date2020-06-04 20:44:37 UTC
BMDB IDBMDB0005056
Secondary Accession Numbers
  • BMDB05056
Metabolite Identification
Common NameEnterodiol
DescriptionEnterodiol, also known as arbo 9 or 2,3-BHBBD, belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Based on a literature review a significant number of articles have been published on Enterodiol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-EnterodiolHMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
Arbo 9HMDB
[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diolHMDB
2,3-BHBBDHMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diolHMDB
EnterodiolHMDB
Chemical FormulaC18H22O4
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
IUPAC Name(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
Traditional Name(-)-enterodiol
CAS Registry Number80226-00-2
SMILES
OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1
InChI KeyDWONJCNDULPHLV-HOTGVXAUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassDibenzylbutanediol lignans
Direct ParentDibenzylbutanediol lignans
Alternative Parents
Substituents
  • Dibenzylbutanediol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP2.65ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.36 m³·mol⁻¹ChemAxon
Polarizability32.76 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2950000000-4ed8a5eb8bfaabb7a263View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6520390000-6840ee48e5d508b92d94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0900000000-6fd5b1caf0b11ab3dd17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-b01fb4b064e58a38e170View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-3900000000-4ed09c20e4a4fb3f3875View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0940000000-786ff272cb009339906fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0940000000-a340102680583cfc68f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0pb9-3900000000-aa3626a0e9a6776858b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0940000000-41e4cc9deb7aa9c799c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-179116fcc815df1446feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0290000000-fd222de6f034fee01c31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ar3-2900000000-ee35613960c900d06fb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0290000000-2de3385ce84eba140c88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0900000000-9fba8f3772864b12ddbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-ebad5296a50b0dcf053aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0398000000-f09da6eee4bc76ff516aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frj-0971000000-bce5b39682ed3570612fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r9-0960000000-6920c1866fa29475fabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-c4358f7b97aab38a1ecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0096000000-fbf3e7cc759ef05d5425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdo-1690000000-046c3b836806f630a4edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0859000000-8fb5cc787a664fd76c34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0690-1950000000-7ae3b12589c277c0e377View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-2940000000-bfd4fbb4059ae278438fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-7d394202ae81237c33a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0393000000-63ea158a62162e087ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r13-0890000000-72542e20683700bfc0c2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.00860 - 0.0132 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.298 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.43 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.496 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005056
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021828
KNApSAcK IDC00000702
Chemspider ID102992
KEGG Compound IDC18166
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnterodiol
METLIN IDNot Available
PubChem Compound115089
PDB IDNot Available
ChEBI ID544560
References
Synthesis ReferenceMahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
  2. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]