Showing metabocard for 2-Methoxyestrone (BMDB0000010)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:16:26 UTC
Update Date2020-06-04 20:40:06 UTC
BMDB IDBMDB0000010
Secondary Accession Numbers
  • BMDB00010
Metabolite Identification
Common Name2-Methoxyestrone
Description2-Methoxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-methoxyestrone is considered to be a steroid lipid molecule. 2-Methoxyestrone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Methoxyestrone exists in all living organisms, ranging from bacteria to humans. 2-Methoxyestrone and S-adenosylhomocysteine can be biosynthesized from S-adenosylmethionine and 2-hydroxyestrone; which is mediated by the enzyme catechol O-methyltransferase. In cattle, 2-methoxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(8S,9S,13S,14S)-3-Hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-oneHMDB
2-Hydroxyestrone 2-methyl etherHMDB
2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-olHMDB
2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-oneHMDB
3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-oneHMDB
3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-oneHMDB
Methoxy-estroneHMDB
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Traditional Name(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number362-08-3
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3
InChI Identifier
InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1
InChI KeyWHEUWNKSCXYKBU-QPWUGHHJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187.0 - 189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.5ALOGPS
logP4.15ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.55 m³·mol⁻¹ChemAxon
Polarizability34.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00167 uMNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00162 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone		 details
BloodDetected and Quantified0.00543 uMNot SpecifiedNot Specified
Treated with estradiol benzoate		 details
HMDB IDHMDB0000010
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021868
KNApSAcK IDNot Available
Chemspider ID389515
KEGG Compound IDC05299
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methoxyestrone
METLIN ID2578
PubChem Compound440624
PDB IDNot Available
ChEBI ID1189
References
Synthesis ReferenceStoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl. (2006), 40 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
S-Adenosylmethionine + 2-Hydroxyestrone → 2-Methoxyestrone + S-Adenosylhomocysteinedetails