Ipecoside

Details

• Internal ID: 1d28203e-a57a-4900-bd23-056c39ff5ffd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,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-(hydroxymethyl)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)CO)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)O)O)O)C=C)O)O
• InChI: InChI=1S/C27H35NO12/c1-4-14-16(8-18-15-9-20(32)19(31)7-13(15)5-6-28(18)12(2)30)17(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)21(10-29)39-27/h4,7,9,11,14,16,18,21-24,26-27,29,31-35H,1,5-6,8,10H2,2-3H3/t14-,16+,18-,21-,22-,23+,24-,26+,27+/m1/s1
• InChI Key: QISXROCIXKXUPS-OWVLCBNUSA-N
• Popularity: 3 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

• 15401-60-2
• AIDS031406
• CHEBI:5952
• MEGxp0_001513
• SCHEMBL5156171
• ACon0_000909
• ACon1_000420
• HY-N2261
• NCGC00169097-03
• methyl (2S,3R,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-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• MS-30242
• CS-0019589
• C09464
• Q27106940
• 2H-PYRAN-5-CARBOXYLIC ACID, 4-[(2-ACETYL-1,2,3,4-TETRAHYDRO-6,7-DIHYDROXY-1-ISOQUINOLINYL)METHYL]-3-ETHENYL-2-(BETA-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-, METHYL ESTER, [2S-[2ALPHA,3BETA,4BETA(S*)]]-IPECOSIDE (6CI,8CI)
• NCGC00169097-03_C27H35NO12_Methyl (2S,3R,4S)-4-{[(1R)-2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydro-1-isoquinolinyl]methyl}-2-(beta-D-glucopyranosyloxy)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5406	54.06%
Caco-2	-	0.8808	88.08%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Nucleus	0.4764	47.64%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.7816	78.16%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6722	67.22%
P-glycoprotein inhibitior	-	0.5082	50.82%
P-glycoprotein substrate	+	0.6029	60.29%
CYP3A4 substrate	+	0.7015	70.15%
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	+	0.5700	57.00%
CYP inhibitory promiscuity	-	0.9023	90.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5980	59.80%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9390	93.90%
Skin irritation	-	0.7670	76.70%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4779	47.79%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.5910	59.10%
Acute Oral Toxicity (c)	III	0.6485	64.85%
Estrogen receptor binding	+	0.8582	85.82%
Androgen receptor binding	+	0.6610	66.10%
Thyroid receptor binding	-	0.4943	49.43%
Glucocorticoid receptor binding	+	0.7049	70.49%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6084	60.84%
Honey bee toxicity	-	0.7185	71.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
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	99.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.70%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.27%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.59%	94.45%
CHEMBL267	P12931	Tyrosine-protein kinase SRC	91.17%	95.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.01%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.90%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.34%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.39%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.87%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.88%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.80%	95.89%
CHEMBL4208	P20618	Proteasome component C5	85.11%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.36%	95.83%
CHEMBL5028	O14672	ADAM10	83.26%	97.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.18%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.23%	91.24%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.62%	97.53%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 442249
• NPASS: NPC252685
• LOTUS: LTS0239896
• wikiData: Q27106940