(Rac)-Tephrosin

Details

• Internal ID: 0e6e274c-1ec0-46e7-915b-ac0980323daf
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 14-hydroxy-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=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)C
• InChI: InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3
• InChI Key: AQBZCCQCDWNNJQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.40 g/mol
• Exact Mass: 410.13655304 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (1R,14R)-14-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12.0^{4,9.0^{15,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
• 14-Hydroxy-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
• HY-N1166A
• CHEBI:182745
• AKOS032948428
• 561-35-3
• CS-0638984

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.6583	65.83%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7878	78.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9129	91.29%
OATP1B3 inhibitior	+	0.9699	96.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8933	89.33%
P-glycoprotein inhibitior	+	0.8684	86.84%
P-glycoprotein substrate	+	0.5675	56.75%
CYP3A4 substrate	+	0.6490	64.90%
CYP2C9 substrate	-	0.6085	60.85%
CYP2D6 substrate	-	0.7751	77.51%
CYP3A4 inhibition	+	0.6438	64.38%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	+	0.7550	75.50%
CYP2D6 inhibition	-	0.5885	58.85%
CYP1A2 inhibition	+	0.7536	75.36%
CYP2C8 inhibition	-	0.6167	61.67%
CYP inhibitory promiscuity	-	0.6981	69.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5833	58.33%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.6551	65.51%
Skin irritation	-	0.8135	81.35%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.7807	78.07%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.5051	50.51%
skin sensitisation	-	0.7504	75.04%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5572	55.72%
Acute Oral Toxicity (c)	III	0.5852	58.52%
Estrogen receptor binding	+	0.8856	88.56%
Androgen receptor binding	+	0.6036	60.36%
Thyroid receptor binding	+	0.8033	80.33%
Glucocorticoid receptor binding	+	0.7904	79.04%
Aromatase binding	+	0.5311	53.11%
PPAR gamma	+	0.8643	86.43%
Honey bee toxicity	-	0.7481	74.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.8968	89.68%

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	96.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.66%	98.95%
CHEMBL4208	P20618	Proteasome component C5	92.05%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.76%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.79%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.62%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.38%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.84%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.78%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.40%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.66%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.38%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.44%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.65%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.90%	97.09%
CHEMBL2535	P11166	Glucose transporter	83.77%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	83.48%	91.19%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.45%	95.71%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.31%	90.24%
CHEMBL1951	P21397	Monoamine oxidase A	82.23%	91.49%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.43%	82.67%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.69%	96.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.29%	92.94%

Plants that contains it

• Amorpha fruticosa
• Antheroporum pierrei
• Derris trifoliata
• Erycibe expansa
• Millettia griffoniana
• Millettia pachycarpa
• Mundulea chapelieri
• Mundulea sericea
• Sarcolobus globosus
• Tephrosia candida
• Tephrosia elata
• Tephrosia virginiana
• Tephrosia vogelii

Cross-Links

• PubChem: 4485131
• LOTUS: LTS0136892
• wikiData: Q104916769