Taleranol

Details

• Internal ID: 3abd35c7-7c9b-46fd-b3b1-d87444fc1176
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-2-one
• SMILES (Canonical): CC1CCCC(CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• SMILES (Isomeric): C[C@H]1CCC[C@H](CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• InChI: InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14-/m0/s1
• InChI Key: DWTTZBARDOXEAM-JSGCOSHPSA-N
• Popularity: 153 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• Taleranol
• 42422-68-4
• Taleranolum
• P-1560
• DTXSID3022532
• HUN219N434
• estrogen P-1560
• RefChem:890786
• DTXCID902532
• (7S,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo(12.4.0)octadeca-1(14),15,17-trien-13-one
• beta zearalanol
• beta-Zeranol
• b-Zeranol
• CHEMBL491510
• (3S,7S)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
• (3S,7S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
• CHEBI:35071
• beta-Zearalanol 10 microg/mL in Acetonitrile
• (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-2-one
• 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*))
• Taleranol [USAN:INN]
• Taleranolum [INN-Latin]
• UNII-HUN219N434
• P 1560
• (3S,7S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one
• ?-ZEARALANOL
• TALERANOL [INN]
• Taleranol (USAN/INN)
• TALERANOL [USAN]
• Epitope ID:933251
• BIDD:ER0109
• SCHEMBL343276
• MSK7201B
• SCHEMBL29554859
• beta-Zearalanol, ~98% (HPLC)
• MSK7201B-100A
• HY-N6740
• (6S,10S)-6-(6,10-Dihydroxyundecyl)-beta-resorcyclic acid mu-lactone
• BBL036409
• BDBM50250268
• MFCD00151077
• MFCD01793835
• STK078170
• AKOS001582522
• CCG-208500
• NCGC00263515-03
• BZ162710
• VS-13472
• CS-0099775
• NS00098477
• D05992
• G12409
• AB01329960-02
• beta-Zearalanol Solution in Acetonitrile, 100ug/mL
• Q27116399
• 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S,7S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.5878	58.78%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6668	66.68%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.8861	88.61%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9321	93.21%
BSEP inhibitior	-	0.6684	66.84%
P-glycoprotein inhibitior	-	0.8500	85.00%
P-glycoprotein substrate	-	0.8852	88.52%
CYP3A4 substrate	+	0.5791	57.91%
CYP2C9 substrate	-	0.5565	55.65%
CYP2D6 substrate	-	0.8260	82.60%
CYP3A4 inhibition	+	0.6622	66.22%
CYP2C9 inhibition	-	0.8967	89.67%
CYP2C19 inhibition	-	0.7774	77.74%
CYP2D6 inhibition	-	0.9136	91.36%
CYP1A2 inhibition	+	0.7088	70.88%
CYP2C8 inhibition	-	0.7048	70.48%
CYP inhibitory promiscuity	-	0.9482	94.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9111	91.11%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.8081	80.81%
Skin irritation	-	0.5466	54.66%
Skin corrosion	-	0.8881	88.81%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3999	39.99%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.7668	76.68%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8921	89.21%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6069	60.69%
Acute Oral Toxicity (c)	III	0.5274	52.74%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.7672	76.72%
Thyroid receptor binding	-	0.5088	50.88%
Glucocorticoid receptor binding	+	0.6689	66.89%
Aromatase binding	-	0.5700	57.00%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9359	93.59%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9605	96.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	891.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	79.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.60%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.57%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.24%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.83%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.47%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.56%	96.12%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.03%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.83%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.21%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.10%	93.99%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.43%	82.67%
CHEMBL217	P14416	Dopamine D2 receptor	84.27%	95.62%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.77%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.20%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.07%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.69%	96.09%
CHEMBL4530	P00488	Coagulation factor XIII	81.67%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.53%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.19%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 65434
• LOTUS: LTS0256675
• wikiData: Q27116399