(-)-Deguelin;(-)-cis-Deguelin

Details

• Internal ID: b000f9b8-66f7-4fe9-9c55-65fa34f63027
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 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=C5C4C3=O)OC)OC)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC)C
• InChI: InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3
• InChI Key: ORDAZKGHSNRHTD-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₆
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.14163842 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• SpecPlus_000410
• DivK1c_006506
• SCHEMBL3365130
• CHEMBL1592086
• KBio1_001450
• ORDAZKGHSNRHTD-UHFFFAOYSA-N
• 3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-
• NCGC00095218-01
• NCGC00095218-02
• FT-0701733
• (1S,14S)-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
• 3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-
• 3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	+	0.8238	82.38%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7581	75.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.9832	98.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9438	94.38%
P-glycoprotein inhibitior	+	0.9158	91.58%
P-glycoprotein substrate	+	0.5453	54.53%
CYP3A4 substrate	+	0.6580	65.80%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.7997	79.97%
CYP3A4 inhibition	+	0.8116	81.16%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	+	0.6513	65.13%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.4587	45.87%
CYP inhibitory promiscuity	+	0.6160	61.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5383	53.83%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.7025	70.25%
Skin irritation	-	0.8285	82.85%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4748	47.48%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.6652	66.52%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.5888	58.88%
Acute Oral Toxicity (c)	III	0.5554	55.54%
Estrogen receptor binding	+	0.9311	93.11%
Androgen receptor binding	+	0.7012	70.12%
Thyroid receptor binding	+	0.7991	79.91%
Glucocorticoid receptor binding	+	0.8363	83.63%
Aromatase binding	-	0.6308	63.08%
PPAR gamma	+	0.8808	88.08%
Honey bee toxicity	+	0.6467	64.67%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9183	91.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	562.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.91%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.71%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.48%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.39%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.23%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.81%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.77%	82.67%
CHEMBL1907	P15144	Aminopeptidase N	85.56%	93.31%
CHEMBL2535	P11166	Glucose transporter	85.13%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.89%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.88%	93.40%
CHEMBL4208	P20618	Proteasome component C5	83.79%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.74%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.51%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.07%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.24%	89.50%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.08%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.43%	97.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.34%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.15%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.06%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.01%	95.71%

Plants that contains it

• Amorpha fruticosa
• Derris elliptica
• Derris trifoliata
• Lonchocarpus salvadorensis
• Millettia pachycarpa
• Tephrosia candida
• Tephrosia fulvinervis
• Tephrosia strigosa
• Tephrosia virginiana
• Tephrosia vogelii

Cross-Links

• PubChem: 606171
• LOTUS: LTS0037865
• wikiData: Q105197385