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

Details

• Internal ID: 872aaef3-1e0c-40dc-b7cf-91862a8f93f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-4-[[(3R)-2-acetyl-5-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-3-yl]methyl]-3-ethenyl-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): CC(=O)N1CC2=C(CC1CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)C(=C(C=C2)OC)O
• SMILES (Isomeric): CC(=O)N1CC2=C(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)OC)O
• InChI: InChI=1S/C28H37NO12/c1-5-16-18(9-15-8-17-14(10-29(15)13(2)31)6-7-20(37-3)22(17)32)19(26(36)38-4)12-39-27(16)41-28-25(35)24(34)23(33)21(11-30)40-28/h5-7,12,15-16,18,21,23-25,27-28,30,32-35H,1,8-11H2,2-4H3/t15-,16+,18-,21-,23-,24+,25-,27-,28+/m0/s1
• InChI Key: OHUCUHDXLDDNMK-YQWNMZROSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₇NO₁₂
• Molecular Weight: 579.60 g/mol
• Exact Mass: 579.23157562 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.29
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5737	57.37%
Caco-2	-	0.8450	84.50%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Nucleus	0.6315	63.15%
OATP2B1 inhibitior	-	0.8656	86.56%
OATP1B1 inhibitior	+	0.8005	80.05%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7886	78.86%
P-glycoprotein inhibitior	-	0.4437	44.37%
P-glycoprotein substrate	+	0.6540	65.40%
CYP3A4 substrate	+	0.7059	70.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.5953	59.53%
CYP2C9 inhibition	-	0.7861	78.61%
CYP2C19 inhibition	-	0.8200	82.00%
CYP2D6 inhibition	-	0.8984	89.84%
CYP1A2 inhibition	-	0.8138	81.38%
CYP2C8 inhibition	+	0.6350	63.50%
CYP inhibitory promiscuity	-	0.8970	89.70%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5631	56.31%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9406	94.06%
Skin irritation	-	0.7700	77.00%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6513	65.13%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5966	59.66%
skin sensitisation	-	0.8586	85.86%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5827	58.27%
Acute Oral Toxicity (c)	III	0.6447	64.47%
Estrogen receptor binding	+	0.8415	84.15%
Androgen receptor binding	+	0.6721	67.21%
Thyroid receptor binding	-	0.4920	49.20%
Glucocorticoid receptor binding	+	0.7403	74.03%
Aromatase binding	+	0.5223	52.23%
PPAR gamma	+	0.6389	63.89%
Honey bee toxicity	-	0.7070	70.70%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9033	90.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.63%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.61%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.43%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.89%	94.45%
CHEMBL4208	P20618	Proteasome component C5	88.11%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.89%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.86%	96.00%
CHEMBL2581	P07339	Cathepsin D	86.97%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	86.69%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.93%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.70%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	84.27%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.17%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.78%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.21%	95.83%
CHEMBL5028	O14672	ADAM10	80.27%	97.50%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 162954225
• LOTUS: LTS0250492
• wikiData: Q105192293