11-Hydroxytephrosin

Details

• Internal ID: 6c1264fc-d25a-4709-a12a-54b282babdec
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1R,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C(C3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C(C3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)O)C
• InChI: InChI=1S/C23H22O8/c1-22(2)6-5-11-14(31-22)8-13(24)19-20(11)30-18-10-29-15-9-17(28-4)16(27-3)7-12(15)23(18,26)21(19)25/h5-9,18,24,26H,10H2,1-4H3/t18-,23-/m1/s1
• InChI Key: OFLCPNIRDVOOEZ-WZONZLPQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₈
• Molecular Weight: 426.40 g/mol
• Exact Mass: 426.13146766 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 72458-85-6
• (1R,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
• 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-6,7a-dihydroxy-9,10-dimethoxy-3,3-dimethyl-, (7aR-cis)-
• 12a-Hydroxy-alpha-toxicarol
• CHEMBL419669
• DTXSID50222755
• HY-N1022
• AKOS032948932
• NCGC00385215-01!
• CS-0016258

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9789	97.89%
Caco-2	+	0.5918	59.18%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8591	85.91%
P-glycoprotein inhibitior	+	0.8049	80.49%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6482	64.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8257	82.57%
CYP3A4 inhibition	-	0.5835	58.35%
CYP2C9 inhibition	-	0.8206	82.06%
CYP2C19 inhibition	+	0.7172	71.72%
CYP2D6 inhibition	-	0.5797	57.97%
CYP1A2 inhibition	+	0.7642	76.42%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6471	64.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5925	59.25%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.6701	67.01%
Skin irritation	-	0.8229	82.29%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.8102	81.02%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7769	77.69%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5099	50.99%
Acute Oral Toxicity (c)	III	0.6709	67.09%
Estrogen receptor binding	+	0.8632	86.32%
Androgen receptor binding	+	0.5887	58.87%
Thyroid receptor binding	+	0.7255	72.55%
Glucocorticoid receptor binding	+	0.7661	76.61%
Aromatase binding	+	0.5692	56.92%
PPAR gamma	+	0.8566	85.66%
Honey bee toxicity	-	0.7102	71.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	+	0.9028	90.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.56%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.34%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.04%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.99%	96.09%
CHEMBL4208	P20618	Proteasome component C5	91.58%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.03%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	89.71%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.59%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.12%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.75%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.15%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.67%	92.94%
CHEMBL2581	P07339	Cathepsin D	87.44%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	87.25%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.07%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.67%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.45%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.22%	97.14%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.20%	82.67%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.15%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.87%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.56%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.43%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.32%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.95%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.39%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.18%	95.71%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Amorpha fruticosa
• Cordia americana
• Glycosmis lanceolata
• Millettia brandisiana
• Pedicularis semitorta
• Sarcolobus globosus
• Scopolia japonica
• Tephrosia candida
• Tephrosia sinapou
• Tephrosia villosa
• Tephrosia viridiflora

Cross-Links

• PubChem: 155725
• NPASS: NPC177480
• ChEMBL: CHEMBL419669
• LOTUS: LTS0113711
• wikiData: Q72481863