methyl (2R,3S,4S)-3-ethenyl-4-(9H-pyrido[3,4-b]indol-1-ylmethyl)-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: b67ba9cc-a54f-4c9d-9061-76fcd0fb8b2f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2R,3S,4S)-3-ethenyl-4-(9H-pyrido[3,4-b]indol-1-ylmethyl)-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): COC(=O)C1=COC(C(C1CC2=NC=CC3=C2NC4=CC=CC=C34)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@@H]([C@H]([C@@H]1CC2=NC=CC3=C2NC4=CC=CC=C34)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H30N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-9,12-13,16,20,22-24,26-27,29-33H,1,10-11H2,2H3/t13-,16-,20+,22+,23-,24+,26+,27-/m0/s1
• InChI Key: VXUXCAXVQWIEMN-ROGHILTESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀N₂O₉
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.19513054 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8390	83.90%
Caco-2	-	0.8605	86.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.3646	36.46%
OATP2B1 inhibitior	-	0.8514	85.14%
OATP1B1 inhibitior	+	0.8087	80.87%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9549	95.49%
P-glycoprotein inhibitior	+	0.6105	61.05%
P-glycoprotein substrate	+	0.5490	54.90%
CYP3A4 substrate	+	0.7113	71.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8500	85.00%
CYP3A4 inhibition	-	0.8939	89.39%
CYP2C9 inhibition	-	0.7892	78.92%
CYP2C19 inhibition	-	0.7923	79.23%
CYP2D6 inhibition	-	0.8177	81.77%
CYP1A2 inhibition	-	0.6484	64.84%
CYP2C8 inhibition	+	0.8056	80.56%
CYP inhibitory promiscuity	-	0.5148	51.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6485	64.85%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9534	95.34%
Skin irritation	-	0.7909	79.09%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7313	73.13%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5836	58.36%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5526	55.26%
Acute Oral Toxicity (c)	III	0.5859	58.59%
Estrogen receptor binding	+	0.8145	81.45%
Androgen receptor binding	+	0.6903	69.03%
Thyroid receptor binding	+	0.6340	63.40%
Glucocorticoid receptor binding	+	0.6243	62.43%
Aromatase binding	+	0.5529	55.29%
PPAR gamma	+	0.7492	74.92%
Honey bee toxicity	-	0.7690	76.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.3745	37.45%

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	98.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.99%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.91%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.74%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.50%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.79%	94.73%
CHEMBL2581	P07339	Cathepsin D	91.00%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.87%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.84%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.80%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.08%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.66%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.83%	86.92%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	84.71%	88.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.84%	86.33%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.15%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.02%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.32%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	80.36%	83.82%

Plants that contains it

• Pauridiantha paucinervis
• Uncaria tomentosa

Cross-Links

• PubChem: 95223021
• LOTUS: LTS0009428
• wikiData: Q105298772