Dracotanoside A

Details

• Internal ID: 9482ccbc-1915-4317-8ee6-f9700eb54fcc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-2-[4-[(10R)-6-oxo-1-[(Z)-3-phenylprop-2-enoyl]-1,5,9-triazacyclotridec-10-yl]phenoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC=C(C=C2)C3CCCN(CCCNC(=O)CCN3)C(=O)C=CC4=CC=CC=C4)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[C@H]3CCCN(CCCNC(=O)CCN3)C(=O)/C=C\C4=CC=CC=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C6=CC=CC=C6)O)O)O)O)O
• InChI: InChI=1S/C44H55N3O13/c1-27-36(50)39(53)41(60-43-40(54)38(52)37(51)33(59-43)26-56-42(55)30-12-6-3-7-13-30)44(57-27)58-31-18-16-29(17-19-31)32-14-8-24-47(25-9-22-46-34(48)21-23-45-32)35(49)20-15-28-10-4-2-5-11-28/h2-7,10-13,15-20,27,32-33,36-41,43-45,50-54H,8-9,14,21-26H2,1H3,(H,46,48)/b20-15-/t27-,32+,33+,36-,37+,38-,39+,40+,41+,43-,44-/m0/s1
• InChI Key: HLZPNUFTRKCSRX-DZBPLUPZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₅N₃O₁₃
• Molecular Weight: 833.90 g/mol
• Exact Mass: 833.37348882 g/mol
• Topological Polar Surface Area (TPSA): 226.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

• CHEMBL557766

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6080	60.80%
Caco-2	-	0.8688	86.88%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6257	62.57%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8506	85.06%
OATP1B3 inhibitior	+	0.9286	92.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8037	80.37%
BSEP inhibitior	+	0.9775	97.75%
P-glycoprotein inhibitior	+	0.7509	75.09%
P-glycoprotein substrate	+	0.6264	62.64%
CYP3A4 substrate	+	0.7072	70.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8476	84.76%
CYP3A4 inhibition	-	0.5075	50.75%
CYP2C9 inhibition	-	0.8736	87.36%
CYP2C19 inhibition	-	0.8636	86.36%
CYP2D6 inhibition	-	0.8096	80.96%
CYP1A2 inhibition	-	0.8854	88.54%
CYP2C8 inhibition	+	0.7523	75.23%
CYP inhibitory promiscuity	-	0.8628	86.28%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6094	60.94%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.7843	78.43%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7134	71.34%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.6323	63.23%
skin sensitisation	-	0.8996	89.96%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9801	98.01%
Acute Oral Toxicity (c)	III	0.5907	59.07%
Estrogen receptor binding	+	0.8136	81.36%
Androgen receptor binding	+	0.6674	66.74%
Thyroid receptor binding	+	0.5521	55.21%
Glucocorticoid receptor binding	+	0.7030	70.30%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.7486	74.86%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.7761	77.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.83%	86.33%
CHEMBL2581	P07339	Cathepsin D	98.02%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.94%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.30%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	96.65%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.17%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.46%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.03%	89.00%
CHEMBL4208	P20618	Proteasome component C5	92.96%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.60%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.56%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.97%	90.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.86%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.48%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.96%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.47%	83.57%
CHEMBL5028	O14672	ADAM10	86.75%	97.50%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	85.59%	91.43%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.22%	90.24%
CHEMBL228	P31645	Serotonin transporter	84.12%	95.51%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.94%	95.83%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.23%	93.00%
CHEMBL3524	P56524	Histone deacetylase 4	82.46%	92.97%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.00%	87.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.70%	93.99%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	80.85%	95.58%

Plants that contains it

• Dracocephalum tanguticum

Cross-Links

• PubChem: 45273474
• LOTUS: LTS0234393
• wikiData: Q105030412