Testolactone

Details

• Internal ID: d3cc495e-5fce-4d68-b2ba-08e730d9b877
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-4,4a,4b,5,6,10b,11,12-octahydro-3H-naphtho[2,1-f]chromene-2,8-dione
• SMILES (Canonical): CC12CCC3C(C1CCC(=O)O2)CCC4=CC(=O)C=CC34C
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CCC(=O)O2)CCC4=CC(=O)C=C[C@]34C
• InChI: 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 Key: BPEWUONYVDABNZ-DZBHQSCQSA-N
• Popularity: 591 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.17254462 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Teslac
• Teolit
• 968-93-4
• Fludestrin
• Testolacton
• 1-Dehydrotestololactone
• 1,2-Didehydrotestololactone
• delta(1)-Testololactone
• Testolattone [DCIT]
• Testolactonum [INN-Latin]
• Testolactona [INN-Spanish]
• Testolactona
• Testolactonum
• Testolattone
• D-Homo-17A-oxaandrosta-1,4-diene-3,17-dione
• SQ 9538
• SQ-9538
• Testololactone, 1-dehydro-
• delta(1)-Dehydrotestolactone
• delta(1)-Testolactone
• 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid delta-lactone
• Testolactone ciii
• Testolactone [USAN:INN]
• NSC-23759
• Teslak
• delta1-Testololactone
• Testololactone, 1,2-didehydro-
• Delta-1-testololactone
• HSDB 3255
• EINECS 213-534-6
• TESLAC (TN)
• Testolactone (USP/INN)
• NSC 23759
• NSC-12173
• 1,2-Dehydrotestololactone
• (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)-dione
• 17alpha-Oxo-D-homo-1,4-androstadiene-3,17-dione
• UNII-6J9BLA949Q
• 3-oxo-13,17-secoandrosta-1,4-dieno-17,13alpha-lactone
• 6J9BLA949Q
• CHEBI:9460
• Testolactone [USAN:USP:INN]
• DTXSID2023644
• (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-4,4a,4b,5,6,10b,11,12-octahydro-3H-naphtho[2,1-f]chromene-2,8-dione
• 1,2,3,4,4a,4b,7,9,10,10a-Decahydro-2-hydroxy-2,4b-dimethyl-7-oxo-1-phenanthrenepropionic acid delta-lactone
• 13,17-Secoandrosta-1,4-dien-17-oic acid, 13-hydroxy-3-oxo-, delta-lactone
• NSC 12173
• 13,17-Secoandrosta-1,4-dien-17-oic acid, 13-hydroxy-3-oxo-, .delta.-lactone
• (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-4,4a,4b,5,6,10a,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromene-2,8(3H)-dione
• 1 Dehydrotestolactone
• 1-Dehydrotestolactone
• .DELTA.1-Testololactone
• .DELTA.1-Dehydrotestolactone
• .DELTA.1-Dehydrotestololactone
• NSC23759
• NCGC00159329-02
• delta-1-testolactone
• therapeutic testolactone
• 17a-Oxa-D-homoandrosta-1,4-diene-3,17-dione
• delta1-Dehydrotestolactone
• TESTOLACTONE [MI]
• TESTOLACTONE [INN]
• D0C7JF
• delta1-Dehydrotestololactone
• TESTOLACTONE [HSDB]
• TESTOLACTONE [USAN]
• SCHEMBL4053
• Testololactone,2-didehydro-
• CHEMBL1571
• TESTOLACTONE [VANDF]
• TESTOLACTONE [USP-RS]
• TESTOLACTONE [WHO-DD]
• DTXCID303644
• GTPL7303
• 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid .delta.-lactone
• HMS3750O07
• TESTOLACTONE [ORANGE BOOK]
• TESTOLACTONE [USP IMPURITY]
• TESTOLACTONE CIII [USP-RS]
• BCP10926
• Tox21_111576
• BDBM50367848
• LMST02020084
• 17a-Oxa-D-homoandrosta-1,17-dione
• D-Homo-17a-oxaandrosta-1,17-dione
• AKOS015840139
• CS-5268
• DB00894
• Bristol Myers SquibbBrand of Testolactone
• CAS-968-93-4
• HY-13763
• NCI60_001908
• Bristol-Myers Squibb Brand of Testolactone
• LS-102968
• C02197
• D00153
• D-homo-17a-oxaandros-ta-1,4-diene-3,17-dione
• Q3985253
• W-100129
• 13,4-dien-17-oic acid, 13-hydroxy-3-oxo-, lactone
• 13-Hydroxy-3-oxo-13,4-dien-17-oic acid .delta.-lactone
• 13,4-dien-17-oic acid, 13-hydroxy-3-oxo-, .delta.-lactone
• 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid lactone
• 13,17-Secoandrosta-1,4-dien-17-oic acid, 13-hydroxy-3-oxo-, lactone
• 13,4-dien-17-oic acid, 13.alpha.-hydroxy-3-oxo-, .delta.-lactone
• 13,17-Secoandrosta-1,4-dien-17-oic acid, 13-hydroxy-3-oxo-, delta-lactone (8CI)
• 13,17-Secoandrosta-1,4-dien-17-oic acid, 13.alpha.-hydroxy-3-oxo-, .delta.-lactone
• 2H-Phenanthro[2,1-b]pyran-2,8(4bH)-dione, 3,4,4a,5,6,10a,10b,11,12,12a-decahydro-10a,12a-dimethyl-, lactone
• 2H-Phenanthro[2,8(4bH)-dione, 3,4,4a,5,6,10a,10b,11,12,12a-decahydro-10a,12a-dimethyl-, lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.8054	80.54%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7090	70.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8723	87.23%
OATP1B3 inhibitior	+	0.9784	97.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.7370	73.70%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8633	86.33%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.7612	76.12%
CYP2C9 inhibition	-	0.8996	89.96%
CYP2C19 inhibition	-	0.8484	84.84%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.7315	73.15%
CYP2C8 inhibition	+	0.5537	55.37%
CYP inhibitory promiscuity	-	0.9224	92.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5765	57.65%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9635	96.35%
Skin irritation	-	0.5424	54.24%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.8427	84.27%
Human Ether-a-go-go-Related Gene inhibition	+	0.8505	85.05%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.5820	58.20%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7155	71.55%
Acute Oral Toxicity (c)	III	0.7657	76.57%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.8720	87.20%
Thyroid receptor binding	+	0.6883	68.83%
Glucocorticoid receptor binding	+	0.8599	85.99%
Aromatase binding	+	0.8061	80.61%
PPAR gamma	-	0.7737	77.37%
Honey bee toxicity	-	0.8604	86.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9825	98.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	35000 nM	Ki	PMID: 2677377

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	95.15%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.33%	91.11%
CHEMBL1871	P10275	Androgen Receptor	93.42%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.82%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.45%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.10%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	89.34%	95.93%
CHEMBL2581	P07339	Cathepsin D	85.08%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.92%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.72%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.94%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.12%	94.80%
CHEMBL1937	Q92769	Histone deacetylase 2	82.63%	94.75%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.45%	96.61%
CHEMBL230	P35354	Cyclooxygenase-2	82.21%	89.63%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.50%	93.04%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.00%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.39%	86.33%

Plants that contains it

• Microcos paniculata

Cross-Links

• PubChem: 13769
• NPASS: NPC30421
• ChEMBL: CHEMBL1571