Showing metabocard for 2-Hydroxyestrone (BMDB0000343)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:57 UTC
Update Date2020-06-04 20:42:14 UTC
BMDB IDBMDB0000343
Secondary Accession Numbers
  • BMDB00343
Metabolite Identification
Common Name2-Hydroxyestrone
Description2-Hydroxyestrone 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-hydroxyestrone is considered to be a steroid lipid molecule. 2-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 2-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 1A1. In addition, S-Adenosylmethionine and 2-hydroxyestrone can be converted into 2-methoxyestrone and S-adenosylhomocysteine through its interaction with the enzyme catechol O-methyltransferase. In cattle, 2-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Dihydroxyestra-1,3,5(10)-trien-17-oneHMDB
2-OHE1HMDB
CatecholestroneHMDB
2-Hydroxyestrone, 4-(14)C-labeledMeSH, HMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,15S)-4,5-dihydroxy-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)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number362-06-1
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3
InChI Identifier
InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
InChI KeySWINWPBPEKHUOD-JPVZDGGYSA-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
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.03ALOGPS
logP4.01ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.06 m³·mol⁻¹ChemAxon
Polarizability32.23 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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000243 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified0.0138 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0177 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone		 details
BloodDetected and Quantified0.0312 uMNot SpecifiedNot Specified
Treated with estradiol benzoate		 details
HMDB IDHMDB0000343
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021966
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05298
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyestrone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID1156
References
Synthesis ReferenceKovacs, Katalin; Rakonczay, Z.; Matkovics, B. Steroids. XXIII. Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol. Acta Physica et Chemica (1973), 19(3), 287-90.
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