Eltanolone (CED0006812)

Record Information

Version

1.0

Creation Date

2016-05-22 05:40:55 UTC

Update Date

2026-08-21 20:09:26 UTC

SynCED ID

CED0006812

Secondary Accession Numbers

CHEM018931

Identification

Common Name

Eltanolone

Class

Small Molecule

Description

Eltanolone is an organic compound with the chemical formula C21H34O2 and an average molecular weight of 318.49 g/mol. Eltanolone belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. The compound is found in or released from two recorded sources: antidepressants, categorized under healthcare, pharmaceuticals, and veterinary products, and non electric simulated smoking devices, categorized under household cleaning and consumer products. The recorded route of exposure for this substance is intravenous. In terms of biological activity, eltanolone interacts with 16 recorded protein targets. It acts as an inhibitor, modulator, or positive allosteric modulator of the Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), Gamma-aminobutyric acid receptor subunit beta-1 (GABRB1), Gamma-aminobutyric acid receptor subunit delta (GABRD), and Gamma-aminobutyric acid receptor subunit pi (GABRP), as well as 12 other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3alpha,5alpha)-3-Hydroxypregnan-20-one	ChEBI
3alpha,5alpha-Tetrahydroprogesterone	ChEBI
3alpha,5alpha-THP	ChEBI
3alpha-Hydroxy-5alpha-dihydroprogesterone	ChEBI
3alpha-Hydroxy-5alpha-pregnan-20-one	ChEBI
3alpha-OH DHP	ChEBI
5alpha-Pregnan-3alpha-ol-20-one	ChEBI
Allopregnan-3alpha-ol-20-one	ChEBI
Allotetrahydroprogesterone	ChEBI
Brexanolona	ChEBI
Brexanolonum	ChEBI
SAGE-547	ChEBI
SGE-102	ChEBI
Zulresso	ChEBI
(3a,5a)-3-Hydroxypregnan-20-one	Generator
(3Α,5α)-3-hydroxypregnan-20-one	Generator
3a,5a-Tetrahydroprogesterone	Generator
3Α,5α-tetrahydroprogesterone	Generator
3a,5a-THP	Generator
3Α,5α-THP	Generator
3a-Hydroxy-5a-dihydroprogesterone	Generator
3Α-hydroxy-5α-dihydroprogesterone	Generator
3a-Hydroxy-5a-pregnan-20-one	Generator
3Α-hydroxy-5α-pregnan-20-one	Generator
3a-OH DHP	Generator
3Α-OH DHP	Generator
5a-Pregnan-3a-ol-20-one	Generator
5Α-pregnan-3α-ol-20-one	Generator
Allopregnan-3a-ol-20-one	Generator
Allopregnan-3α-ol-20-one	Generator
(+)-3a-Hydroxy-5a-pregnan-20-one	HMDB
(3a)-Allopregnanolone	HMDB
3-a-Tetrahydroprogesterone	HMDB
3-alpha-Tetrahydroprogesterone	HMDB
3a,5a-Pregnanolone	HMDB
3a-Hydroxy-5a-pregnane-20-one	HMDB
5a-Pregnane-3a-ol-20-one	HMDB
3-Hydroxypregnan-20-one	HMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3	HMDB
Pregnan-3alpha-ol-20-one	HMDB
Pregnanolone, (3alpha)-isomer	HMDB
3 Hydroxypregnan 20 one	HMDB
3 alpha Hydroxy 5 alpha pregnan 20 one	HMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-one	HMDB
Pregnan 3alpha ol 20 one	HMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5	HMDB
(+)-3alpha-Hydroxy-5alpha-pregnan-20-one	HMDB
(+)-3Α-hydroxy-5α-pregnan-20-one	HMDB
(3alpha)-Allopregnanolone	HMDB
(3Α)-allopregnanolone	HMDB
3alpha,5alpha-Pregnanolone	HMDB
3alpha-Hydroxy-5alpha-pregnane-20-one	HMDB
3Α,5α-pregnanolone	HMDB
3Α-hydroxy-5α-pregnane-20-one	HMDB
5alpha-Pregnane-3alpha-ol-20-one	HMDB
5Α-pregnane-3α-ol-20-one	HMDB
Allopregnanolone	MeSH, ChEBI

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Mass

318.494 g/mol

Monoisotopic Mass

318.256 g/mol

CAS Registry Number

128-20-1

IUPAC Name

1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

Traditional Name

1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

AURFZBICLPNKBZ-SYBPFIFISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy-5alpha-pregnan-20-one (CHEBI:50169 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030156 )

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

metabolite (PMC2643957 )?A chemical produced during metabolism process, as an intermediate or end-product
agonist (PMC6108593 )?
steroid hormone (PMC9820491 )?
sedative (PMC3774751 )?
anticonvulsant (PMC3774751 , PMC6708749 )?
general anaesthetic (PMC3671381 )?
anaesthetic (PMC3774751 , PMC6708749 )?
anxiolytic drug (PMC6708749 )?

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	0.0014 g/L	ALOGPS
logP	4.28	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	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	92.91 m³·mol⁻¹	ChemAxon
Polarizability	38.52 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
GC-MS	GC-MS Spectrum	splash10-0udi-6910000000-837b37f206729753b640	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0udi-6910000000-837b37f206729753b640	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-1174-0292000000-fb2c0f3a1cfddb10cb08	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-2139000000-ab8a6de8f5a129af086e	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	splash10-0uxr-0129000000-90e5fcb36022dd1ba688	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uxr-0396000000-4c39fe7ccd8e0c86e179	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2490000000-7ac55935cc0d4da95860	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0029000000-fa09e69c9c0b6736d2e7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0069000000-d1d57e3e1a99da4ed11f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zg0-1193000000-44d1597a59ac11f16a41	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gb9-0019000000-5b53b3ba37ccafca449f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0lgi-1797000000-c11629ffa10cac4be118	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4m-8910000000-2813a600e98ff5997275	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-bbaa566ea695ae62f84e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0029000000-ac1c6a15538469151b6c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ks-0093000000-db70f670eb2440b743f9	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2363.0 Log mg/kg [1300:4200]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
Alzheimer's disease	Associated With?	increase	A neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.	PMC9820491
schizophrenia	Associated With?	Not Available	A psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (DO)	PMC2643957
schizophrenia	Has Therapeutic Effect On	Not Available	A psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (DO)	PMC9820491
schizophrenia	Decreased in Blood In	decrease	A psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (DO)	PMC5524961
glaucoma	Has Therapeutic Effect On	Not Available	A disorder characterized by an increase in pressure in the eyeball due to obstruction of the aqueous humor outflow. (NCI CTCAE)	PMC9098829
bipolar disorder	Associated With?	Not Available	A mood disorder that involves alternating periods of mania and depression. (DO)	PMC2643957
postpartum depression	Not Available	Not Available	An endogenous depression that involves intense, sustained and sometimes disabling depression experienced by women after giving birth. (DO)	PMC12500787 , PMC12816930
anxiety disorder	Decreased in Blood In	decrease	Not Available	PMC5524961
Oxidative Stress	Has Therapeutic Effect On	Not Available	Not Available	PMC7756608
depressive disorder	Associated With?	increase	Not Available	PMC8011861
Mental deterioration	Associated With?	decrease	Not Available	PMC9820491
Hypoxia	Associated With?	increase	Not Available	PMC12399127
Hypoxia	Elevated in Blood In	increase	Not Available	PMC12399127
brain disorder	Not Available	Not Available	Not Available	PMC10801763
premenstrual dysphoric disorder	Decreased in Blood In	decrease	Not Available	PMC5524961
Immobilization	Associated With?	decrease	Not Available	PMC3671381

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000377	Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs02334	Pond Water	Aquatic systems & sediments	PMC3671381 , PMC3671381

Pathways

1 pathwayPathway Source: PathBank

Brexanolone Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	Prediction Confidence Score 0.613 Applicability Domain 0.675 Statistical Significance 1.20e-04 Supporting Reference Compounds 54 E-value 0.934191
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	Prediction Confidence Score 0.57 Applicability Domain 0.675 Statistical Significance 7.00e-05 Supporting Reference Compounds 33 E-value 0.544945
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	Prediction Confidence Score 0.561 Applicability Domain 1.0 Statistical Significance 1.20e-04 Supporting Reference Compounds 49 E-value 0.934191
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	Prediction Confidence Score 0.523 Applicability Domain 0.587 Statistical Significance 1.20e-04 Supporting Reference Compounds 21 E-value 0.934191
Click to view 3D structure	Cycloartenol-C-24-methyltransferase	Q9LM02	Arabidopsis thaliana	Predicted (SEA)	Prediction Confidence Score 0.482 Applicability Domain 0.482 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	P11413	Humans	Predicted (SEA)	Prediction Confidence Score 0.481 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	Q9GRG7	Trypanosoma brucei	Predicted (SEA)	Prediction Confidence Score 0.423 Applicability Domain 0.587 Statistical Significance 1.50e-04 Supporting Reference Compounds 2 E-value 1.16774
Click to view 3D structure	Potassium-transporting ATPase alpha chain 2	P54707	Humans	Predicted (SEA)	Prediction Confidence Score 0.408 Applicability Domain 0.436 Statistical Significance 3.00e-05 Supporting Reference Compounds 2 E-value 0.233548
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2	Q11205	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.403 Applicability Domain 0.403 Statistical Significance 1.40e-04 Supporting Reference Compounds 1 E-value 1.08989
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.401 Applicability Domain 0.472 Statistical Significance 0.0014 Supporting Reference Compounds 73 E-value 10.6653
Click to view 3D structure	Gamma-aminobutyric acid type B receptor subunit 1	Q9Z0U4	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.391 Applicability Domain 0.391 Statistical Significance 2.80e-04 Supporting Reference Compounds 1 E-value 2.17978
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	Prediction Confidence Score 0.387 Applicability Domain 0.472 Statistical Significance 0.0028 Supporting Reference Compounds 146 E-value 22.187
Click to view 3D structure	E3 ubiquitin-protein ligase ZFP91	Q96JP5	Humans	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 0.381 Statistical Significance 3.00e-05 Supporting Reference Compounds 1 E-value 0.233548
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.377 Applicability Domain 0.472 Statistical Significance 3.50e-04 Supporting Reference Compounds 19 E-value 2.72472
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 3	O35627	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.372 Applicability Domain 0.553 Statistical Significance 3.00e-05 Supporting Reference Compounds 2 E-value 0.233548
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 0.558 Statistical Significance 0.0034 Supporting Reference Compounds 94 E-value 26.858
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	Prediction Confidence Score 0.359 Applicability Domain 0.472 Statistical Significance 0.0034 Supporting Reference Compounds 154 E-value 26.3909
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	Prediction Confidence Score 0.355 Applicability Domain 0.472 Statistical Significance 0.0023 Supporting Reference Compounds 74 E-value 18.061
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.353 Applicability Domain 0.472 Statistical Significance 0.0012 Supporting Reference Compounds 40 E-value 9.6533
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	Prediction Confidence Score 0.351 Applicability Domain 0.383 Statistical Significance 5.70e-04 Supporting Reference Compounds 19 E-value 4.43741
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P18405	Humans	Predicted (SEA)	Prediction Confidence Score 0.342 Applicability Domain 0.383 Statistical Significance 5.00e-04 Supporting Reference Compounds 14 E-value 3.89246
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	Prediction Confidence Score 0.335 Applicability Domain 0.472 Statistical Significance 0.0075 Supporting Reference Compounds 201 E-value 58.4648
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.472 Statistical Significance 0.002 Supporting Reference Compounds 104 E-value 15.2584
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	Prediction Confidence Score 0.317 Applicability Domain 0.44 Statistical Significance 0.0064 Supporting Reference Compounds 127 E-value 49.5121
Click to view 3D structure	Eukaryotic initiation factor 4A-I	P60843	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.31 Applicability Domain 0.354 Statistical Significance 2.00e-05 Supporting Reference Compounds 2 E-value 0.155698