ethisterone (CED0011397)

Record Information

Version

1.0

Creation Date

2016-06-03 11:59:12 UTC

Update Date

2026-08-21 19:46:14 UTC

Accession Number

CHEM044273

Identification

Common Name

ethisterone

Class

Small Molecule

Description

Ethisterone is an organic compound with the chemical formula C21H28O2 and an average molecular weight of 312.45 g/mol. Ethisterone belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds. It is further classified within the superclass of lipids and lipid-like molecules. The compound has been identified in or released from 20 recorded sources across multiple sectors. Within aquatic systems and sediments, it is found in seawater, freshwater, surface water, and groundwater. It is also present in drinking water and water supply sources, including tap water, bottled water, and desalinated water. In the realm of wastewater, sanitation, and biosolids, ethisterone is detected in industrial wastewater, mine wastewater, wastewater treatment effluent, and unspecified wastewater. Other recorded sources include marine, shipping, and aquaculture environments, specifically ballast water and bilge water, as well as irrigation water used in agriculture and land management. Additionally, the compound is associated with appliances, HVAC, and refrigerants, specifically water heaters and water coolers, among three other sectors. Recorded routes of exposure for ethisterone include oral ingestion, inhalation, and touch.

Contaminant Type

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17-beta-Hydroxy-17-alpha-ethynyl-4-androsten-3-one	ChEBI
17-Ethynyl-17beta-hydroxyandrost-4-en-3-one	ChEBI
17-Hydroxy-17alpha-pregn-4-en-20-yn-3-one	ChEBI
17alpha-Ethinyltestosterone	ChEBI
17alpha-Ethynyl-17beta-hydroxyandrost-4-en-3-one	ChEBI
17alpha-Ethynyltestosterone	ChEBI
Aethisteron	ChEBI
Aethisteronum	ChEBI
Anhydrohydroxyprogesterone	ChEBI
Anhydroxyprogesterone	ChEBI
Ethisteronum	ChEBI
Ethynyltestosterone	ChEBI
Etisterona	ChEBI
Lutocylol	ChEBI
Nugestoral	ChEBI
Ora-lutin	ChEBI
Pranone	ChEBI
Prodroxan	ChEBI
Produxan	ChEBI
Progestab	ChEBI
Progestoral	ChEBI
Syngestrotabs	ChEBI
Trosinone	ChEBI
17alpha-Ethinyl testosterone	Kegg
Progestolets	Kegg
17-b-Hydroxy-17-a-ethynyl-4-androsten-3-one	Generator
17-Β-hydroxy-17-α-ethynyl-4-androsten-3-one	Generator
17-Ethynyl-17b-hydroxyandrost-4-en-3-one	Generator
17-Ethynyl-17β-hydroxyandrost-4-en-3-one	Generator
17-Hydroxy-17a-pregn-4-en-20-yn-3-one	Generator
17-Hydroxy-17α-pregn-4-en-20-yn-3-one	Generator
17a-Ethinyltestosterone	Generator
17Α-ethinyltestosterone	Generator
17a-Ethynyl-17b-hydroxyandrost-4-en-3-one	Generator
17Α-ethynyl-17β-hydroxyandrost-4-en-3-one	Generator
17a-Ethynyltestosterone	Generator
17Α-ethynyltestosterone	Generator
17a-Ethinyl testosterone	Generator
17Α-ethinyl testosterone	Generator
17 alpha Ethynyltestosterone	HMDB
17 alpha-Ethynyltestosterone	HMDB
Pregneninolone	HMDB

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Mass

312.446 g/mol

Monoisotopic Mass

312.209 g/mol

CAS Registry Number

434-03-7

IUPAC Name

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

Traditional Name

ethisterone

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C

InChI Identifier

InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

CHNXZKVNWQUJIB-CEGNMAFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:34749 )
tertiary alcohol (CHEBI:34749 )
3-oxo Delta(4)-steroid (CHEBI:34749 )
17beta-hydroxy steroid (CHEBI:34749 )
Pregnane and derivatives [Fig] (C14487 )

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	0.0091 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.52	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	17.59	ChemAxon
pKa (Strongest Basic)	-1.7	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	0	ChemAxon
Refractivity	91.9 m³·mol⁻¹	ChemAxon
Polarizability	36.45 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-0490000000-70da7a36790d59e5aec1	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0aou-1259000000-15d6bab9887e263c6273	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-0169000000-c3a3859c9249ba72e662	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0btj-0291000000-04631559fd3d6eeaf96d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0v4r-2490000000-b96a17af7ffa84b61a5e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-714673f1ccbbef0d107a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0039000000-edc9d17d6776c137fae1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052g-0090000000-09a994bdce08144c9cb6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0292-0092000000-87469d8eaf22bca0423c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01dj-0950000000-872492e74ef79726b1fc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-3940000000-1fb184dfb1c47b20c927	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-152b659b4891e36b54f3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-2fd97457f6fe96a074b4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-0394000000-326a8e9cae724f94ba3a	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
2009.0	Log mg/kg	[1100:3600]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
3	Irrigation water	Agriculture & land management	Not Available
27	Water Coolers	Appliances, HVAC & refrigerants	Not Available
43	Water heaters	Appliances, HVAC & refrigerants	Not Available
50	Groundwater	Aquatic systems & sediments	Not Available
51	Surface water	Aquatic systems & sediments	Not Available
52	Seawater	Aquatic systems & sediments	Not Available
53	Freshwater	Aquatic systems & sediments	Not Available
70	Stormwater runoff	Automotive & urban infrastructure	Not Available
88	Waterproofing sprays	Building & Construction	Not Available
115	Drinking water	Drinking water & water supply	Not Available
116	Tap water	Drinking water & water supply	Not Available
117	Bottled water	Drinking water & water supply	Not Available
118	Desalinated water	Drinking water & water supply	Not Available
181	Ballast water	Marine, shipping & aquaculture	Not Available
182	Bilge water	Marine, shipping & aquaculture	Not Available
468	Industrial wastewater	Wastewater, sanitation & biosolids	Not Available
470	Wastewater treatment effluent	Wastewater, sanitation & biosolids	Not Available
475	Mine wastewater	Wastewater, sanitation & biosolids	Not Available
477	Wastewater, unspecified	Wastewater, sanitation & biosolids	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
620	Card Games	Recreation & sports surfaces	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	0.233548
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	0.155698
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	3.81461
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	15.7255
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	2.02408
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	4.67095
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	0.778492
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	9.41976
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	33.3195
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	108.055
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	36.8227
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P18405	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	2.95827
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	27.1694
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	200.617
Click to view 3D structure	Solute carrier organic anion transporter family member 1A1	P46720	Rattus norvegicus	Predicted (SEA)	1.63483
Click to view 3D structure	Solute carrier family 22 member 3	O88446	Rattus norvegicus	Predicted (SEA)	1.01204
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 3	O35627	Mus musculus	Predicted (SEA)	0.233548