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

Details

• Internal ID: 36f5230b-3fa4-4fe0-b2fc-03a496c4b015
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-4-[[(1R,4R)-2-acetyl-4,6,7-trihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): CC(=O)N1CC(C2=CC(=C(C=C2C1CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)O)O)O
• SMILES (Isomeric): CC(=O)N1C[C@@H](C2=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)O)O)O)C=C)O)O)O
• InChI: InChI=1S/C27H35NO13/c1-4-12-13(5-17-14-6-18(31)19(32)7-15(14)20(33)8-28(17)11(2)30)16(25(37)38-3)10-39-26(12)41-27-24(36)23(35)22(34)21(9-29)40-27/h4,6-7,10,12-13,17,20-24,26-27,29,31-36H,1,5,8-9H2,2-3H3/t12-,13+,17-,20+,21-,22-,23+,24-,26+,27+/m1/s1
• InChI Key: IZNGUQUMRJUVTA-UOZAMYLJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₅NO₁₃
• Molecular Weight: 581.60 g/mol
• Exact Mass: 581.21084017 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -0.93
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5449	54.49%
Caco-2	-	0.8860	88.60%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.5733	57.33%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.7750	77.50%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5486	54.86%
P-glycoprotein inhibitior	-	0.5521	55.21%
P-glycoprotein substrate	+	0.5727	57.27%
CYP3A4 substrate	+	0.6871	68.71%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.7203	72.03%
CYP2C9 inhibition	-	0.7747	77.47%
CYP2C19 inhibition	-	0.7961	79.61%
CYP2D6 inhibition	-	0.8913	89.13%
CYP1A2 inhibition	-	0.7758	77.58%
CYP2C8 inhibition	+	0.5609	56.09%
CYP inhibitory promiscuity	-	0.9128	91.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5729	57.29%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.7694	76.94%
Skin corrosion	-	0.9322	93.22%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4453	44.53%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.6968	69.68%
skin sensitisation	-	0.8542	85.42%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6738	67.38%
Acute Oral Toxicity (c)	III	0.6388	63.88%
Estrogen receptor binding	+	0.8254	82.54%
Androgen receptor binding	+	0.6876	68.76%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.6699	66.99%
Aromatase binding	-	0.5196	51.96%
PPAR gamma	+	0.6156	61.56%
Honey bee toxicity	-	0.7437	74.37%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.8346	83.46%

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	99.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.29%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.23%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.92%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.61%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	88.24%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.94%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.47%	90.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.22%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.98%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.54%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.36%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.26%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.46%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.31%	95.89%
CHEMBL5028	O14672	ADAM10	81.88%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.34%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.31%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.51%	92.50%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 101175459
• LOTUS: LTS0247066
• wikiData: Q105123319