Dehydrotoxicarol

Details

• Internal ID: 2af0eefe-5025-41a3-afb2-ce23d4ee4d70
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC)O)C
• InChI: InChI=1S/C23H20O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,24H,10H2,1-4H3
• InChI Key: HDDUSYQWBVKRGV-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₇
• Molecular Weight: 408.40 g/mol
• Exact Mass: 408.12090297 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.26
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 59086-93-0
• 6a,12a-Dehydrotoxicarol
• 7a,13a-Didehydrotoxicarol
• CHEMBL122787
• 6a,12a-Dehydro-alpha-toxcarol
• 6a,12a-Dehydro-alpha-toxicarol
• 6a,12a-Didehydro-alpha-toxcarol
• 11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one
• DTXSID70974542
• BDBM50473404
• LMPK12060069
• AKOS032948257
• 11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12.0^{4,9.0^{15,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one
• 6-Hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-[1]benzopyrano[4',3':5,6]pyrano[2,3-f][1]benzopyran-7(13H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9829	98.29%
Caco-2	+	0.7211	72.11%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7972	79.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9154	91.54%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9206	92.06%
P-glycoprotein inhibitior	+	0.8782	87.82%
P-glycoprotein substrate	-	0.5268	52.68%
CYP3A4 substrate	+	0.6454	64.54%
CYP2C9 substrate	-	0.6192	61.92%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	+	0.7167	71.67%
CYP2C9 inhibition	-	0.8979	89.79%
CYP2C19 inhibition	+	0.7988	79.88%
CYP2D6 inhibition	+	0.5538	55.38%
CYP1A2 inhibition	+	0.7908	79.08%
CYP2C8 inhibition	+	0.4585	45.85%
CYP inhibitory promiscuity	-	0.6239	62.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5567	55.67%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.6669	66.69%
Skin irritation	-	0.8121	81.21%
Skin corrosion	-	0.9671	96.71%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6532	65.32%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7242	72.42%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6856	68.56%
Acute Oral Toxicity (c)	III	0.5838	58.38%
Estrogen receptor binding	+	0.9234	92.34%
Androgen receptor binding	+	0.6968	69.68%
Thyroid receptor binding	+	0.7323	73.23%
Glucocorticoid receptor binding	+	0.8530	85.30%
Aromatase binding	+	0.6484	64.84%
PPAR gamma	+	0.9107	91.07%
Honey bee toxicity	-	0.7555	75.55%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5049	50.49%
Fish aquatic toxicity	+	0.8875	88.75%

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	99.40%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.67%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.33%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.24%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.99%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.93%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.59%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.19%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.15%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.92%	93.99%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.02%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.53%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.29%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.21%	92.94%
CHEMBL4208	P20618	Proteasome component C5	86.01%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.56%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.56%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.35%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.32%	92.62%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.15%	80.96%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.47%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.13%	91.19%
CHEMBL2535	P11166	Glucose transporter	82.09%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.24%	97.09%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.28%	95.53%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Amorpha fruticosa
• Cordia americana
• Derris elliptica
• Derris ovalifolia
• Derris trifoliata
• Glycosmis lanceolata
• Millettia brandisiana
• Pedicularis semitorta
• Scopolia japonica
• Tephrosia candida
• Tephrosia sinapou

Cross-Links

• PubChem: 5491616
• NPASS: NPC40037
• ChEMBL: CHEMBL122787
• LOTUS: LTS0180783
• wikiData: Q72461902