ChemFOnt: Showing chemical card for 2-Methoxyestrone (CFc000000002)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:33:49 UTC

Chemfont ID

CFc000000002

Molecule Identification

Common Name

2-Methoxyestrone

Definition

2-Methoxyestrone (or 2-ME1) 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 or steroid derivative. It is a by-product of estrone and 2-hydroxyestrone metabolism and has been detected in all mammals. More specifically, 2-methoxyestrone is an endogenous, naturally occurring methoxylated catechol estrogen and a metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 2-hydroxyestrone. 2-Methoxyestrone is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone has been determined to be 10.81 (PMID: 516114 ). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17). Unlike estrone but similarly to 2-hydroxyestrone and 2-methoxyestradiol, 2-methoxyestrone has very low affinity for the estrogen receptor and lacks significant estrogenic activity (PMID: 10865186 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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-one	HMDB
2-Hydroxyestrone 2-methyl ether	HMDB
2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol	HMDB
2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one	HMDB
Methoxy-estrone	HMDB

Chemical Formula

C₁₉H₂₄O₃

Average Molecular Weight

300.3921

Monoisotopic Molecular Weight

300.172544634

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 Number

362-08-3

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 Key

WHEUWNKSCXYKBU-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens 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 Framework

Aromatic homopolycyclic compounds

External Descriptors

phenols (CHEBI:1189 )
alicyclic ketone (CHEBI:1189 )
17-oxo steroid (CHEBI:1189 )
3-hydroxy steroid (CHEBI:1189 )
C18 steroids (estrogens) and derivatives (C05299 )
C18 steroids (estrogens) and derivatives (LMST02010033 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Pituitary, hypothalamus, or pineal disorder

Prolactinoma (HMDB: HMDB0000010)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000010)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 9812172)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000010)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000010)

Source

Endogenous

Endogenous (HMDB: HMDB0000010)

Animal

Animal (HMDB: HMDB0000010)

Exogenous

Food

Food (HMDB: HMDB0000010)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000010)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000010)

Molecular messenger

Hormone (HMDB: HMDB0000010)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000010)

Pharmaceutical industry

Biomarker

Prolactinoma (MarkerDB: MDB00000004)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0075 g/L	ALOGPS
logP	3.5	ALOGPS
logP	4.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.55 m³·mol⁻¹	ChemAxon
Polarizability	34.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000010

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021868

KNApSAcK ID

Not Available

Chemspider ID

389515

KEGG Compound ID

C05299

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Methoxyestrone

METLIN ID

2578

PubChem Compound

440624

PDB ID

Not Available

ChEBI ID

1189

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Stoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl. (2006), 40 pp.

Showing chemical card for 2-Methoxyestrone (CFc000000002)

MOL for CFc000000002 (2-Methoxyestrone)

3D MOL for CFc000000002 (2-Methoxyestrone)

3D SDF for CFc000000002 (2-Methoxyestrone)

3D-SDF for CFc000000002 (2-Methoxyestrone)

PDB for CFc000000002 (2-Methoxyestrone)

3D PDB for CFc000000002 (2-Methoxyestrone)

SMILES for CFc000000002 (2-Methoxyestrone)

INCHI for CFc000000002 (2-Methoxyestrone)

Structure for CFc000000002 (2-Methoxyestrone)

3D Structure for CFc000000002 (2-Methoxyestrone)