methyl (2S,3S,4S)-4-[[(1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: 69fe8704-5fbb-4479-9d01-82fe0b18c785
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3S,4S)-4-[[(1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): CC(=O)N1CCC2=CC(=C(C=C2C1CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)C=C)O)O
• SMILES (Isomeric): CC(=O)N1CCC2=CC(=C(C=C2[C@H]1C[C@H]3[C@@H]([C@@H](OC=C3C(=O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)C=C)O)O
• InChI: InChI=1S/C33H45NO17/c1-4-15-17(8-19-16-9-21(38)20(37)7-14(16)5-6-34(19)13(2)36)18(30(45)46-3)11-47-31(15)51-33-29(44)27(42)25(40)23(50-33)12-48-32-28(43)26(41)24(39)22(10-35)49-32/h4,7,9,11,15,17,19,22-29,31-33,35,37-44H,1,5-6,8,10,12H2,2-3H3/t15-,17-,19+,22+,23+,24+,25+,26-,27-,28+,29+,31-,32-,33-/m0/s1
• InChI Key: NZRIAMCQBSTDCE-JOFGNYIISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₅NO₁₇
• Molecular Weight: 727.70 g/mol
• Exact Mass: 727.26874897 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.59
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5406	54.06%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Nucleus	0.4764	47.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7883	78.83%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6494	64.94%
P-glycoprotein inhibitior	+	0.6338	63.38%
P-glycoprotein substrate	+	0.6485	64.85%
CYP3A4 substrate	+	0.7124	71.24%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.7003	70.03%
CYP2C9 inhibition	-	0.7570	75.70%
CYP2C19 inhibition	-	0.7805	78.05%
CYP2D6 inhibition	-	0.8968	89.68%
CYP1A2 inhibition	-	0.7456	74.56%
CYP2C8 inhibition	+	0.6348	63.48%
CYP inhibitory promiscuity	-	0.9023	90.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5980	59.80%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9237	92.37%
Skin irritation	-	0.7670	76.70%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7015	70.15%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.7698	76.98%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.4532	45.32%
Acute Oral Toxicity (c)	III	0.6485	64.85%
Estrogen receptor binding	+	0.8378	83.78%
Androgen receptor binding	+	0.6575	65.75%
Thyroid receptor binding	-	0.5151	51.51%
Glucocorticoid receptor binding	+	0.6200	62.00%
Aromatase binding	+	0.5509	55.09%
PPAR gamma	+	0.6710	67.10%
Honey bee toxicity	-	0.7054	70.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9233	92.33%

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	99.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.64%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.67%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.94%	94.45%
CHEMBL267	P12931	Tyrosine-protein kinase SRC	90.33%	95.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.84%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.01%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.54%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.61%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.57%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.30%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.76%	95.83%
CHEMBL4208	P20618	Proteasome component C5	84.44%	90.00%
CHEMBL5028	O14672	ADAM10	84.30%	97.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.08%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.91%	90.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.02%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	80.38%	94.73%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 162993138
• LOTUS: LTS0063233
• wikiData: Q105188403