Tibolone (CED0006416)

Record Information

Version

1.0

Creation Date

2016-05-22 03:47:14 UTC

Update Date

2026-08-21 19:46:12 UTC

Accession Number

CHEM016905

Identification

Common Name

Tibolone

Class

Small Molecule

Description

Tibolone belongs to the oxosteroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound has the chemical formula C21H28O2 and an average molecular weight of 312.45 g/mol. Within the broader classification of lipids and lipid-like molecules, it is identified as an estrogen. Tibolone has been recorded as being found in or released from six different sources. These include healthcare, pharmaceuticals & veterinary products, specifically estrogens; household cleaning & consumer products, such as tobacco product cases and non electric simulated smoking devices; electrical & electronic equipment, including relays and magnets; and building & construction materials, specifically floors. The recorded route of exposure for this compound is oral. Regarding its biological activity, tibolone has one recorded protein target, the estrogen receptor (ESR1), for which it acts as both an agonist and an antagonist.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17R)-17-Hydroxy-7alpha-methyl-19-norpregn-5(10)-en-20-yn-3-one	ChEBI
(7alpha,17alpha)-17-Hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one	ChEBI
(7alpha,17beta)-17-Ethynyl-17-hydroxy-7-methylestr-5(10)en-3-one	ChEBI
17-Hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one	ChEBI
Tibolona	ChEBI
Tibolonum	ChEBI
(17R)-17-Hydroxy-7a-methyl-19-norpregn-5(10)-en-20-yn-3-one	Generator
(17R)-17-Hydroxy-7α-methyl-19-norpregn-5(10)-en-20-yn-3-one	Generator
(7a,17a)-17-Hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one	Generator
(7Α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one	Generator
(7a,17b)-17-Ethynyl-17-hydroxy-7-methylestr-5(10)en-3-one	Generator
(7Α,17β)-17-ethynyl-17-hydroxy-7-methylestr-5(10)en-3-one	Generator
17-Hydroxy-7a-methyl-19-nor-17a-pregn-5(10)-en-20-yn-3-one	Generator
17-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one	Generator
Organon brand OF tibolone	MeSH
Liviella	MeSH
Org OD 14	MeSH
Tibilone	MeSH
Berenguer infale brand OF tibolone	MeSH
Livial	MeSH
Tibolone	MeSH
Boltin	MeSH
Org OD14	MeSH

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Mass

312.453 g/mol

Monoisotopic Mass

312.209 g/mol

CAS Registry Number

5630-53-5

IUPAC Name

(1S,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-2(7)-en-5-one

Traditional Name

livial

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC(=O)CC3)C[C@@]([H])(C)[C@@]21[H]

InChI Identifier

InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1

InChI Key

WZDGZWOAQTVYBX-XOINTXKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Cyclohexenone
Ynone
Cyclic alcohol
Tertiary alcohol
Ketone
Cyclic ketone
Acetylide
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:32223 )
17beta-hydroxy steroid (CHEBI:32223 )

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	0.0072 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3.1	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	16.27	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	91.73 m³·mol⁻¹	ChemAxon
Polarizability	36.77 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
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0971000000-09912161a9fdfe89ed83	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0971000000-09912161a9fdfe89ed83	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0179000000-e2c55e2addfba37f9a88	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bta-0191000000-71bf0cf485b512f47502	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00y1-1590000000-09be4fdc8333874366c5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0019000000-c7326af7a58062034340	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0049000000-7c1502e83bf7094416a0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052g-2090000000-441a3bb49bdef8fac4da	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
2486.0	Log mg/kg	[1400:4400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
319	Estrogens	Healthcare, pharmaceuticals & veterinary products	Not Available
497	Floors	Building & Construction	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Tibolone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	2.88042
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	0.778492
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	18.9952
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	5.0602
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	20.9414
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	9.9647
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	98.1679
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	324.787
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	64.6149
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	75.903
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	248.183
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	513.26
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	1194.6
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	3580.6
Click to view 3D structure	Glucocorticoid receptor	Q9N1U3	Sus scrofa	Predicted (SEA)	2.56902
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	314.822
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	103.072
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	5124.19
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	100.036
Click to view 3D structure	Sex hormone-binding globulin	P08689	Rattus norvegicus	Predicted (SEA)	10.5875
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	22.4984
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	32.4631
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	321.284
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	3639.68
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	757.784