alpha-Toxicarol

Details

• Internal ID: bd75fbcf-7ee5-415e-bd9d-d5f8f247a334
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1S,14S)-11-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=C(C3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C(C3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)O)C
• InChI: InChI=1S/C23H22O7/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/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1
• InChI Key: JLTNCZQNGBLBGO-MOPGFXCFSA-N
• Popularity: 11 references 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: 3.90
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• TOXICAROL
• 82-09-7
• CHEBI:9643
• (1S,14S)-11-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
• 5-19-10-00641 (Beilstein Handbook Reference)
• CHEMBL508992
• SCHEMBL4742046
• LMPK12060027
• AKOS032949012
• Q27108457

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9829	98.29%
Caco-2	+	0.7891	78.91%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7972	79.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8970	89.70%
P-glycoprotein inhibitior	+	0.8327	83.27%
P-glycoprotein substrate	-	0.5559	55.59%
CYP3A4 substrate	+	0.6530	65.30%
CYP2C9 substrate	+	0.5981	59.81%
CYP2D6 substrate	-	0.8360	83.60%
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	+	0.5256	52.56%
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	-	0.6826	68.26%
Skin irritation	-	0.8121	81.21%
Skin corrosion	-	0.9671	96.71%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6848	68.48%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.7242	72.42%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5713	57.13%
Acute Oral Toxicity (c)	III	0.5838	58.38%
Estrogen receptor binding	+	0.9137	91.37%
Androgen receptor binding	+	0.6757	67.57%
Thyroid receptor binding	+	0.7438	74.38%
Glucocorticoid receptor binding	+	0.8316	83.16%
Aromatase binding	-	0.5752	57.52%
PPAR gamma	+	0.9091	90.91%
Honey bee toxicity	-	0.5581	55.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5851	58.51%
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	99.23%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.22%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.15%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.81%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.97%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.76%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.27%	93.99%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.17%	82.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.65%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.37%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.69%	99.23%
CHEMBL4208	P20618	Proteasome component C5	85.13%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.41%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.05%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	83.98%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.83%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.98%	94.00%
CHEMBL2535	P11166	Glucose transporter	82.93%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.99%	93.40%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.98%	80.96%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.71%	99.15%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Cordia americana
• Derris elliptica
• Derris trifoliata
• Glycosmis lanceolata
• Lonchocarpus salvadorensis
• Millettia brandisiana
• Millettia pachycarpa
• Pedicularis semitorta
• Podocarpus macrophyllus
• Scopolia japonica
• Tephrosia candida
• Tephrosia fulvinervis
• Tephrosia major
• Tephrosia sinapou
• Tephrosia tepicana

Cross-Links

• PubChem: 442826
• NPASS: NPC120593
• LOTUS: LTS0248767
• wikiData: Q27108457