Karwinskia toxin T-544

Details

• Internal ID: 11a63383-0ec4-4248-a294-da2e5b8d7466
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 3,8,9-trihydroxy-7-(10-hydroxy-7,9-dimethoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl)-3-methyl-2,4-dihydroanthracen-1-one
• SMILES (Canonical): CC1CC2=C(C3=C(C(=CC(=C3)OC)OC)C(=C2C(O1)C)O)C4=C(C5=C(C6=C(CC(CC6=O)(C)O)C=C5C=C4)O)O
• SMILES (Isomeric): CC1CC2=C(C3=C(C(=CC(=C3)OC)OC)C(=C2C(O1)C)O)C4=C(C5=C(C6=C(CC(CC6=O)(C)O)C=C5C=C4)O)O
• InChI: InChI=1S/C32H32O8/c1-14-8-20-24(15(2)40-14)30(35)28-21(10-18(38-4)11-23(28)39-5)27(20)19-7-6-16-9-17-12-32(3,37)13-22(33)25(17)31(36)26(16)29(19)34/h6-7,9-11,14-15,34-37H,8,12-13H2,1-5H3
• InChI Key: OFXNQLFWWFUNRK-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₂O₈
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.20971797 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.70
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 56678-09-2
• Tullidinol
• NSC235814
• 3,8,9-trihydroxy-7-(10-hydroxy-7,9-dimethoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl)-3-methyl-2,4-dihydroanthracen-1-one
• T-544 toxin
• Toxin T 544
• T544
• T 544
• Toxin 544, Karwinskia
• T-544
• 3,8,9-Trihydroxy-7-(10-hydroxy-7,9-dimethoxy-1,3-dimethylbenzo[g]isochroman-5-yl)-3-methyl-2,3,4-trihydroanthracen-1-one
• DTXSID90972126
• NSC 235814
• NSC-235814
• 1(2H)-Anthracenone, 3,4-dihydro-7-(3,4-dihydro-10-hydroxy-7,9-dimethoxy-1,3-dimethyl-1H-naphtho(2,3-c)pyran-5-yl)-3,8,9-trihydroxy-3-methyl-
• 1(2H)-Anthracenone, 7-(3,4-dihydro-10-hydroxy-7,9-dimethoxy-1,3-dimethyl-1H-naphtho(2,3-c)pyran-5-yl)-3,4-dihydro-3,8,9-trihydroxy-3-methyl-
• 3,8,9-Trihydroxy-7-(10-hydroxy-7,9-dimethoxy-1,3-dimethyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-5-yl)-3-methyl-3,4-dihydroanthracen-1(2H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9532	95.32%
Caco-2	-	0.6510	65.10%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6604	66.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8377	83.77%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9400	94.00%
P-glycoprotein inhibitior	+	0.7722	77.22%
P-glycoprotein substrate	+	0.6535	65.35%
CYP3A4 substrate	+	0.6892	68.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8003	80.03%
CYP3A4 inhibition	-	0.5294	52.94%
CYP2C9 inhibition	-	0.7419	74.19%
CYP2C19 inhibition	-	0.6199	61.99%
CYP2D6 inhibition	-	0.7957	79.57%
CYP1A2 inhibition	+	0.6128	61.28%
CYP2C8 inhibition	+	0.6180	61.80%
CYP inhibitory promiscuity	-	0.6367	63.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8768	87.68%
Skin irritation	-	0.7689	76.89%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.6563	65.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7167	71.67%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6108	61.08%
skin sensitisation	-	0.9129	91.29%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6840	68.40%
Acute Oral Toxicity (c)	I	0.3627	36.27%
Estrogen receptor binding	+	0.8472	84.72%
Androgen receptor binding	+	0.5920	59.20%
Thyroid receptor binding	+	0.6615	66.15%
Glucocorticoid receptor binding	+	0.8729	87.29%
Aromatase binding	+	0.7585	75.85%
PPAR gamma	+	0.6722	67.22%
Honey bee toxicity	-	0.8125	81.25%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.9270	92.70%

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	99.85%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	97.26%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	96.91%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.76%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.59%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.28%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.70%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	90.21%	94.42%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	90.15%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.95%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.90%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.49%	99.15%
CHEMBL1907	P15144	Aminopeptidase N	88.34%	93.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.85%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.68%	97.09%
CHEMBL2535	P11166	Glucose transporter	87.03%	98.75%
CHEMBL4208	P20618	Proteasome component C5	86.96%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.49%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.59%	93.99%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.78%	100.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.49%	96.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.43%	94.45%
CHEMBL2056	P21728	Dopamine D1 receptor	82.41%	91.00%

Plants that contains it

• Karwinskia humboldtiana
• Karwinskia parvifolia

Cross-Links

• PubChem: 99832
• LOTUS: LTS0193958
• wikiData: Q82955848