Tuberculatin

Details

• Internal ID: 056bfc3a-0947-442c-ad3e-14a20b0254cf
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(CO4)(CO)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@H]4[C@@H]([C@](CO4)(CO)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• InChI: InChI=1S/C26H24O11/c1-31-17-6-13-14(7-18(17)32-2)22(37-25-23(28)26(30,9-27)10-34-25)15-8-33-24(29)21(15)20(13)12-3-4-16-19(5-12)36-11-35-16/h3-7,23,25,27-28,30H,8-11H2,1-2H3/t23-,25-,26+/m0/s1
• InChI Key: XIARCTMJGANPJU-AYRHNUGRSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₄O₁₁
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.13186158 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.74
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Diphyllin apioside
• CHEMBL471889
• SCHEMBL24578795
• HY-N10941
• AKOS040763351
• CS-0637704
• 9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8210	82.10%
Caco-2	-	0.6937	69.37%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5841	58.41%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.9199	91.99%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9812	98.12%
P-glycoprotein inhibitior	+	0.7428	74.28%
P-glycoprotein substrate	-	0.5964	59.64%
CYP3A4 substrate	+	0.6663	66.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	+	0.5462	54.62%
CYP2C9 inhibition	-	0.8424	84.24%
CYP2C19 inhibition	-	0.8099	80.99%
CYP2D6 inhibition	-	0.8905	89.05%
CYP1A2 inhibition	-	0.8847	88.47%
CYP2C8 inhibition	+	0.6594	65.94%
CYP inhibitory promiscuity	-	0.6146	61.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5326	53.26%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9222	92.22%
Skin irritation	-	0.8002	80.02%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7169	71.69%
Micronuclear	+	0.7133	71.33%
Hepatotoxicity	+	0.6251	62.51%
skin sensitisation	-	0.8503	85.03%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5112	51.12%
Acute Oral Toxicity (c)	III	0.6954	69.54%
Estrogen receptor binding	+	0.8722	87.22%
Androgen receptor binding	+	0.7155	71.55%
Thyroid receptor binding	+	0.6341	63.41%
Glucocorticoid receptor binding	+	0.8760	87.60%
Aromatase binding	+	0.6029	60.29%
PPAR gamma	+	0.6820	68.20%
Honey bee toxicity	-	0.7307	73.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8106	81.06%

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	99.29%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.73%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.99%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.59%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.45%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.18%	92.62%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.84%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.81%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.37%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.91%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.38%	100.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	87.11%	95.53%
CHEMBL2535	P11166	Glucose transporter	86.56%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.22%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.57%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.93%	92.94%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.83%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.52%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	83.32%	93.31%
CHEMBL226	P30542	Adenosine A1 receptor	83.04%	95.93%
CHEMBL5555	O00767	Acyl-CoA desaturase	83.02%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.46%	95.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.82%	95.89%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.69%	92.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.27%	85.14%
CHEMBL4302	P08183	P-glycoprotein 1	80.08%	92.98%

Plants that contains it

• Euphorbia franckiana
• Garcinia subelliptica
• Geranium nepalense
• Grindelia ciliata
• Haplophyllum linifolium subsp. rosmarinifolium
• Haplophyllum tuberculatum
• Hertia intermedia
• Justicia patentiflora
• Justicia procumbens
• Kippistia suaedifolia
• Pelargonium reniforme
• Polygala amarella
• Swertia angustifolia

Cross-Links

• PubChem: 10391676
• NPASS: NPC184624
• LOTUS: LTS0255881
• wikiData: Q105328393