Desogestrel (CED0006244)

Record Information

Version

1.0

Creation Date

2016-05-22 03:39:39 UTC

Update Date

2026-08-21 22:56:45 UTC

Accession Number

CHEM016659

Identification

Common Name

Desogestrel

Class

Small Molecule

Description

Desogestrel is an organic compound with the chemical formula C22H30O and an average molecular weight of 310.47 g/mol. Desogestrel belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This substance is categorized under the superclass of lipids and lipid-like molecules. The compound is found in or released from four recorded sources. These include pharmaceuticals, veterinary products, and healthcare items, specifically progestogens and estrogens in combination as well as hormonal contraceptives for systemic use. Additionally, it is associated with household cleaning and consumer products, specifically non electric simulated smoking devices, and electrical and electronic equipment, specifically electrically stimulated smoking devices. The recorded route of exposure for this compound is oral. At the molecular level, desogestrel interacts with two recorded protein targets. It acts as an agonist of the estrogen receptor (ESR1) and the progesterone receptor (PGR).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol	ChEBI
Cerazette	ChEBI
Desogestrelum	ChEBI
13-Ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-ol	Generator
13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol	Generator
13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol	HMDB
13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol	HMDB
Marvelon	HMDB
Organon brand OF desogestrel	HMDB
alpha-Pregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-18,19-dinor-17	HMDB

Chemical Formula

C₂₂H₃₀O

Average Molecular Mass

310.473 g/mol

Monoisotopic Mass

310.230 g/mol

CAS Registry Number

54024-22-5

IUPAC Name

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

Traditional Name

mircette

SMILES

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

InChI Identifier

InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

InChI Key

RPLCPCMSCLEKRS-BPIQYHPVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

17-hydroxysteroid
Hydroxysteroid
Estrane-skeleton
Delta-4-steroid
Ynone
Tertiary alcohol
Cyclic alcohol
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4453 )
17beta-hydroxy steroid (CHEBI:4453 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C07629 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030104 )

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	0.003 g/L	ALOGPS
logP	4.3	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.73 m³·mol⁻¹	ChemAxon
Polarizability	37.54 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	splash10-001i-1290000000-9475ca0bf2f8bacf92e6	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0uxr-2259000000-f9baa1c23b9a2a4c85d3	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	splash10-03di-0059000000-aa79c27f1567e9a1bbb8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-1191000000-6107987c3071dc2f2bce	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6x-6490000000-517254a3119708155490	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-a4421231af9da549d34e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0049000000-5671ecc974cfc97a058d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-055f-0090000000-f5a84a6463500aef18be	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-bd627e7955e8c8fb1ae0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-bd627e7955e8c8fb1ae0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-0091000000-dde68f19d9643d308450	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0239000000-4888d713f81fa1d000c4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-0951000000-5d7499db9a7f85012ce3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-003r-1930000000-2bccd3c0a6581ed2a815	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
954.0	Log mg/kg	[540:1700]	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
322	Progestogens and estrogens in combination	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Desogestrel Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	92.3292
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	12.4559
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	5.29375
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	28.9599
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	12.6894
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	44.1405
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	221.17
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	3086.72
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	273.484
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	513.727
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	3506.56
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	3154.29
Click to view 3D structure	Ferritin heavy chain	P02794	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	1590.93
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	6631.04
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	3921.42
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	3902.5
Click to view 3D structure	Glucocorticoid receptor	Q9N1U3	Sus scrofa	Predicted (SEA)	5.52729
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	1964.06
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	365.891
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	88.5924
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7386.96
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	50.2127
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	1293.85
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	6318.32