(1R,15S,16R,17S)-16-ethenyl-5-hydroxy-4,15-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-14-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,12-tetraen-11-one

Details

• Internal ID: 6c1f28d3-7b15-40a2-8f4d-a5cda749d039
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (1R,15S,16R,17S)-16-ethenyl-5-hydroxy-4,15-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-14-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,12-tetraen-11-one
• SMILES (Canonical): C=CC1C2CC3C4=CC(=C(C=C4CCN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)O)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2C[C@@H]3C4=CC(=C(C=C4CCN3C(=O)C2=CO[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C30H39NO15/c1-2-12-14-6-16-13-7-18(43-29-25(39)23(37)21(35)19(8-32)44-29)17(34)5-11(13)3-4-31(16)27(41)15(14)10-42-28(12)46-30-26(40)24(38)22(36)20(9-33)45-30/h2,5,7,10,12,14,16,19-26,28-30,32-40H,1,3-4,6,8-9H2/t12-,14+,16-,19-,20-,21-,22-,23+,24+,25-,26-,28+,29-,30+/m1/s1
• InChI Key: KGOGAQZTTUQNRT-HSQWGZBISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₉NO₁₅
• Molecular Weight: 653.60 g/mol
• Exact Mass: 653.23196954 g/mol
• Topological Polar Surface Area (TPSA): 249.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -3.12
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7014	70.14%
Caco-2	-	0.8916	89.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.6210	62.10%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.8491	84.91%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7421	74.21%
P-glycoprotein inhibitior	-	0.4328	43.28%
P-glycoprotein substrate	-	0.5656	56.56%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8430	84.30%
CYP3A4 inhibition	-	0.8964	89.64%
CYP2C9 inhibition	-	0.8435	84.35%
CYP2C19 inhibition	-	0.8474	84.74%
CYP2D6 inhibition	-	0.8270	82.70%
CYP1A2 inhibition	-	0.6357	63.57%
CYP2C8 inhibition	+	0.5495	54.95%
CYP inhibitory promiscuity	-	0.8343	83.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5588	55.88%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9150	91.50%
Skin irritation	-	0.7616	76.16%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8389	83.89%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7106	71.06%
Acute Oral Toxicity (c)	III	0.6098	60.98%
Estrogen receptor binding	+	0.8264	82.64%
Androgen receptor binding	+	0.6459	64.59%
Thyroid receptor binding	-	0.5087	50.87%
Glucocorticoid receptor binding	-	0.5158	51.58%
Aromatase binding	-	0.4841	48.41%
PPAR gamma	+	0.7079	70.79%
Honey bee toxicity	-	0.7123	71.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8488	84.88%

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	98.61%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.95%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.09%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.59%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.52%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.79%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.48%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.39%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.91%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.61%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.94%	90.71%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.59%	90.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.95%	95.83%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.92%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.41%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.72%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.34%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.98%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.89%	97.21%
CHEMBL226	P30542	Adenosine A1 receptor	80.15%	95.93%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 101175456
• LOTUS: LTS0115358
• wikiData: Q105140875