methyl (2R,3S,4S)-4-[[(1R)-2-acetyl-7,8-dihydroxy-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: fa11a343-ccc4-46f9-b887-100d8acce83c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2R,3S,4S)-4-[[(1R)-2-acetyl-7,8-dihydroxy-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)N1CCC2=C(C1CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)C(=C(C=C2)O)O
• SMILES (Isomeric): CC(=O)N1CCC2=C([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)C(=C(C=C2)O)O
• InChI: InChI=1S/C27H35NO12/c1-4-14-15(9-17-20-13(5-6-18(31)21(20)32)7-8-28(17)12(2)30)16(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)19(10-29)39-27/h4-6,11,14-15,17,19,22-24,26-27,29,31-35H,1,7-10H2,2-3H3/t14-,15-,17+,19+,22+,23-,24+,26+,27-/m0/s1
• InChI Key: XNYSLIQSJYSIDP-AWRUKDLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₅NO₁₂
• Molecular Weight: 565.60 g/mol
• Exact Mass: 565.21592555 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5744	57.44%
Caco-2	-	0.8602	86.02%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4515	45.15%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.7804	78.04%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8771	87.71%
P-glycoprotein inhibitior	-	0.5222	52.22%
P-glycoprotein substrate	+	0.5970	59.70%
CYP3A4 substrate	+	0.7081	70.81%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.7694	76.94%
CYP2C9 inhibition	-	0.7975	79.75%
CYP2C19 inhibition	-	0.7923	79.23%
CYP2D6 inhibition	-	0.9031	90.31%
CYP1A2 inhibition	-	0.7597	75.97%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.9020	90.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5693	56.93%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9407	94.07%
Skin irritation	-	0.7709	77.09%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4149	41.49%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8637	86.37%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7007	70.07%
Acute Oral Toxicity (c)	III	0.6414	64.14%
Estrogen receptor binding	+	0.8563	85.63%
Androgen receptor binding	+	0.7073	70.73%
Thyroid receptor binding	-	0.5208	52.08%
Glucocorticoid receptor binding	+	0.7079	70.79%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5908	59.08%
Honey bee toxicity	-	0.7655	76.55%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9175	91.75%

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	99.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.07%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.23%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.07%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.32%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.90%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.18%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.93%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.85%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.17%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.99%	94.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.75%	94.00%
CHEMBL5028	O14672	ADAM10	83.37%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.28%	91.19%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 163022837
• LOTUS: LTS0221441
• wikiData: Q105332146