methyl (2S,3R,4S)-3-ethenyl-4-(9H-pyrido[3,4-b]indol-1-ylmethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: 9f400f77-e725-4ec3-a7ac-ba33a8f503d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-4-(9H-pyrido[3,4-b]indol-1-ylmethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(=CO3)C(=O)OC)CC4=NC=CC5=C4NC6=CC=CC=C56)C=C)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3[C@@H]([C@@H](C(=CO3)C(=O)OC)CC4=NC=CC5=C4NC6=CC=CC=C56)C=C)O)O)O)O
• InChI: InChI=1S/C37H38N2O12/c1-4-20-23(16-26-31-22(13-14-38-26)21-7-5-6-8-25(21)39-31)24(35(45)47-3)17-49-36(20)51-37-34(44)33(43)32(42)29(50-37)18-48-30(41)12-10-19-9-11-27(40)28(15-19)46-2/h4-15,17,20,23,29,32-34,36-37,39-40,42-44H,1,16,18H2,2-3H3/b12-10+/t20-,23+,29-,32-,33+,34-,36+,37+/m1/s1
• InChI Key: LWFNFQXOPUCHCN-DIBTWPROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₈N₂O₁₂
• Molecular Weight: 702.70 g/mol
• Exact Mass: 702.24247465 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8418	84.18%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Nucleus	0.5318	53.18%
OATP2B1 inhibitior	+	0.7042	70.42%
OATP1B1 inhibitior	+	0.8214	82.14%
OATP1B3 inhibitior	+	0.9388	93.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8721	87.21%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	+	0.6930	69.30%
CYP3A4 substrate	+	0.7361	73.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.6964	69.64%
CYP2C9 inhibition	-	0.6499	64.99%
CYP2C19 inhibition	-	0.6625	66.25%
CYP2D6 inhibition	-	0.7806	78.06%
CYP1A2 inhibition	-	0.5792	57.92%
CYP2C8 inhibition	+	0.8921	89.21%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.7966	79.66%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7196	71.96%
Micronuclear	+	0.7959	79.59%
Hepatotoxicity	-	0.5216	52.16%
skin sensitisation	-	0.8282	82.82%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8367	83.67%
Acute Oral Toxicity (c)	III	0.6131	61.31%
Estrogen receptor binding	+	0.8298	82.98%
Androgen receptor binding	+	0.7604	76.04%
Thyroid receptor binding	+	0.6034	60.34%
Glucocorticoid receptor binding	+	0.6858	68.58%
Aromatase binding	+	0.5193	51.93%
PPAR gamma	+	0.7371	73.71%
Honey bee toxicity	-	0.7181	71.81%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9050	90.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.85%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.79%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.21%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.35%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.13%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.70%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.23%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.80%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL4302	P08183	P-glycoprotein 1	88.93%	92.98%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.79%	92.62%
CHEMBL4040	P28482	MAP kinase ERK2	88.79%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.00%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.58%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.09%	99.23%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	87.05%	92.29%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	86.88%	97.03%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	86.84%	98.21%
CHEMBL2535	P11166	Glucose transporter	86.16%	98.75%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.79%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.64%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.41%	95.83%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.51%	89.62%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.18%	95.17%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.29%	96.00%

Plants that contains it

• Palicourea adusta

Cross-Links

• PubChem: 101926057
• LOTUS: LTS0064734
• wikiData: Q105158253