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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015031
Secondary Accession Numbers
  • HMDB15031
Metabolite Identification
Common NameTestolactone
DescriptionTestolactone, also known as teslac, belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Thus, testolactone is considered to be a steroid lipid molecule. Testolactone is a drug which is used for palliative treatment of advanced breast cancer in postmenopausal women. It works by blocking the production of estrogens, which helps prevent the growth of breast cancers that are stimulated by estrogens. Testolactone was first approved for medical use in the United States in 1970. Testolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Androstenedione, a 19-carbon steroid hormone produced in the adrenal glands and the gonads, is where estrone synthesis originates and is the source of estrogen in postmenopausal women. In vitro studies report that the aromatase inhibition may be noncompetitive and irreversible, and could possibly account for the persistence of this drug's effect on estrogen synthesis after drug withdrawal. However, it has been reported to still be marketed in the United States by Bristol-Myers Squibb under the brand name Teslac. Testolactone has also been used to postpone precocious puberty because of its ability to block estrogen production. In addition to its activity as an aromatase inhibitor, testolactone also reportedly possesses some anabolic activity and weak androgenic activity via binding to and activation of the androgen receptor (AR). Testolactone (INN, USAN) (brand name Teslac) is a non-selective, irreversible, steroidal aromatase inhibitor which is used as an antineoplastic drug to treat advanced-stage breast cancer.
Structure
Data?1600362241
Synonyms
ValueSource
(4AS,4BR,10ar,10BS,12as)-10a,12a-dimethyl-3,4,4a,5,6,10a,10b,11,12,12a-decahydro-2H-naphtho[2,1-F]chromene-2,8(4BH)-dioneChEBI
1,2-DidehydrotestololactoneChEBI
1-DehydrotestololactoneChEBI
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid delta-lactoneChEBI
D-homo-17a-Oxaandrosta-1,4-diene-3,17-dioneChEBI
delta(1)-TestololactoneChEBI
TeslacChEBI
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate delta-lactoneGenerator
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate Δ-lactoneGenerator
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid Δ-lactoneGenerator
Δ(1)-testololactoneGenerator
1-DehydrotestolactoneMeSH, HMDB
1 DehydrotestolactoneMeSH, HMDB
delta(1)-TestolactoneMeSH, HMDB
1,2-DehydrotestololactoneHMDB
TestolactoneHMDB
delta1-DehydrotestololactoneHMDB
delta1-TestolactoneHMDB
delta1-TestololactoneHMDB
Δ1-DehydrotestololactoneHMDB
Δ1-TestolactoneHMDB
Δ1-TestololactoneHMDB
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione
Traditional Name(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione
CAS Registry Number968-93-4
SMILES
[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]
InChI Identifier
InChI=1S/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1
InChI KeyBPEWUONYVDABNZ-DZBHQSCQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP2.33ALOGPS
logP3.23ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)18.84ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.79 m³·mol⁻¹ChemAxon
Polarizability33.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.52131661259
DarkChem[M-H]-164.55331661259
DeepCCS[M-2H]-206.89930932474
DeepCCS[M+Na]+181.80730932474
AllCCS[M+H]+174.832859911
AllCCS[M+H-H2O]+171.532859911
AllCCS[M+NH4]+177.832859911
AllCCS[M+Na]+178.732859911
AllCCS[M-H]-180.832859911
AllCCS[M+Na-2H]-180.732859911
AllCCS[M+HCOO]-180.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Testolactone[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]3642.7Standard polar33892256
Testolactone[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]2431.0Standard non polar33892256
Testolactone[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]2940.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Testolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-0690000000-49e361148d5394e26c862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Testolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 10V, Positive-QTOFsplash10-0udi-0096000000-cdcc5f9f8e7f59492fe02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 20V, Positive-QTOFsplash10-0pb9-0291000000-34b2744abd958e22e6482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 40V, Positive-QTOFsplash10-0fdo-4590000000-e7db8fb6ab17e0d604212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 10V, Negative-QTOFsplash10-052b-0090000000-8efa821a1c48e1557a702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 20V, Negative-QTOFsplash10-052b-0090000000-0995c390179d691601d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 40V, Negative-QTOFsplash10-0006-7090000000-a32554f7118b988d790a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 10V, Positive-QTOFsplash10-0udi-0029000000-4635acc995962c6e08b02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 20V, Positive-QTOFsplash10-0znc-0892000000-2b63265434d11c2899042021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 40V, Positive-QTOFsplash10-0ab9-2900000000-5c09785873ed37a7d2c92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 10V, Negative-QTOFsplash10-0002-0090000000-dd82c6133109d0e6e28e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 20V, Negative-QTOFsplash10-0002-0090000000-46bc79dbf2f9c8a576582021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testolactone 40V, Negative-QTOFsplash10-001j-0390000000-357d4c19f4162151e2162021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00894 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00894 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00894
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13172
KEGG Compound IDC02197
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTestolactone
METLIN IDNot Available
PubChem Compound13769
PDB IDNot Available
ChEBI ID9460
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [PubMed:11792932 ]
  3. Herzog AG, Klein P, Jacobs AR: Testosterone versus testosterone and testolactone in treating reproductive and sexual dysfunction in men with epilepsy and hypogonadism. Neurology. 1998 Mar;50(3):782-4. [PubMed:9521275 ]
  4. Dunkel L: Use of aromatase inhibitors to increase final height. Mol Cell Endocrinol. 2006 Jul 25;254-255:207-16. [PubMed:16766117 ]
  5. Cepa MM, Tavares da Silva EJ, Correia-da-Silva G, Roleira FM, Teixeira NA: Structure-activity relationships of new A,D-ring modified steroids as aromatase inhibitors: design, synthesis, and biological activity evaluation. J Med Chem. 2005 Oct 6;48(20):6379-85. [PubMed:16190763 ]