Etonogestrel (CED0006472)

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:49 UTC

Update Date

2026-05-14 16:25:14 UTC

Accession Number

CHEM019247

Identification

Common Name

Etonogestrel

Class

Small Molecule

Description

Etonogestrel is an organic compound with the formula C22H28O2 and an average molecular weight of 324.46 g/mol. Etonogestrel belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. It acts as an agonist of the Progesterone receptor (PGR). In terms of application, the compound is used in healthcare, pharmaceuticals, and veterinary products as a hormonal contraceptive for systemic use. Recorded exposure routes include subcutaneous and vaginal administration. Additionally, etonogestrel is used in plastics, specifically in Low-Density Polyethylene, High-Density Polyethylene, and Polyamide.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ketodesogestrel	ChEBI
3-Oxodesogestrel	ChEBI
Etonogestrelum	ChEBI
Implanon	ChEBI
3-Keto-desogestrel	HMDB
3-oxo Desogestrel	HMDB
Nourypharma brand OF 3-keto-desogestrel	HMDB
Organon brand OF 3-keto-desogestrel	HMDB
Nexplanon	HMDB
13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one	HMDB

Chemical Formula

C₂₂H₂₈O₂

Average Molecular Mass

324.457 g/mol

Monoisotopic Mass

324.209 g/mol

CAS Registry Number

54048-10-1

IUPAC Name

(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

implanon

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

InChI Key

GCKFUYQCUCGESZ-BPIQYHPVSA-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-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Ynone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:50777 )
3-oxo steroid (CHEBI:50777 )
3-oxo Delta(4)-steroid (CHEBI:50777 )
17beta-hydroxy steroid (CHEBI:50777 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	3.19	ALOGPS
logP	3.6	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.35 m³·mol⁻¹	ChemAxon
Polarizability	37.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0002-0490000000-f19630a72a1129f10bf7	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0159-1229000000-b23d32067ab6b2d731e5	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0029000000-79342e3a25ab8393fcf3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-0293000000-7fba9509e41963586a90	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kto-4490000000-f371adb91716a8b2a97c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-c3db9c113e21a37a1583	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0039000000-ec939c554edfb95cfa48	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05mp-0091000000-4d1d86fd76db62f4f394	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0019000000-1228eaafd8c11f200430	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-0911000000-325050413fe1b814de62	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0910000000-a6075096a7ada684910b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-60a003deddef6c16e354	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-ef1eddb9bebeae35c843	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00vj-0093000000-272f3ab06ca7eae7c3ac	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2319.0	Log mg/kg	[1300:4100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
317	Hormonal contraceptives for systemic use	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

3 pathways

Etonogestrel Action Pathway

Etonogestrel Drug Metabolism Action Pathway

Etonogestrel Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	5.2159
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	3.58106
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	1.86838
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	9.49761
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	46.0089
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	38.6132
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	25.0674
Click to view 3D structure	Glucocorticoid receptor	Q9N1U3	Sus scrofa	Predicted (SEA)	2.17978
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	69.6751
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	177.107
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	20.63
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1402.77
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	1898.28
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	11.0546
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	467.173
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	44.3741
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	87.5804
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	261.573
Click to view 3D structure	Glucocorticoid receptor	A0A8C0QLS2	Canis lupus familiaris	Predicted (SEA)	2.41333
Click to view 3D structure	Glucocorticoid receptor	P06537	Mus musculus	Predicted (SEA)	8.25202
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	2141.48
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	3935.82
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	36.1999
Click to view 3D structure	Sex hormone-binding globulin	P08689	Rattus norvegicus	Predicted (SEA)	8.71911
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	105.252