1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

Details

• Internal ID: 6533f70b-04ad-4116-bf18-865fb859ae4f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
• SMILES (Canonical): COC(=O)C1=COC(C(C1CC2=C3C(=CC(=N2)C(=O)O)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC2=C3C(=CC(=N2)C(=O)O)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H30N2O11/c1-3-12-14(8-18-21-15(9-19(29-18)25(35)36)13-6-4-5-7-17(13)30-21)16(26(37)38-2)11-39-27(12)41-28-24(34)23(33)22(32)20(10-31)40-28/h3-7,9,11-12,14,20,22-24,27-28,30-34H,1,8,10H2,2H3,(H,35,36)/t12-,14+,20-,22-,23+,24-,27+,28+/m1/s1
• InChI Key: APMZCJQXEGDAIT-HFPCJCFDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀N₂O₁₁
• Molecular Weight: 570.50 g/mol
• Exact Mass: 570.18495978 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• 21451-50-3
• 1-(((2S,3R,4S)-5-(Methoxycarbonyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2H-pyran-4-yl)methyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7538	75.38%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.3710	37.10%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.7799	77.99%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8919	89.19%
P-glycoprotein inhibitior	+	0.5898	58.98%
P-glycoprotein substrate	+	0.5190	51.90%
CYP3A4 substrate	+	0.6936	69.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.9024	90.24%
CYP2C9 inhibition	-	0.7586	75.86%
CYP2C19 inhibition	-	0.7919	79.19%
CYP2D6 inhibition	-	0.8579	85.79%
CYP1A2 inhibition	-	0.7051	70.51%
CYP2C8 inhibition	+	0.8113	81.13%
CYP inhibitory promiscuity	-	0.6373	63.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6416	64.16%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9377	93.77%
Skin irritation	-	0.7903	79.03%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	+	0.5477	54.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4385	43.85%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8447	84.47%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5102	51.02%
Acute Oral Toxicity (c)	III	0.5908	59.08%
Estrogen receptor binding	+	0.7893	78.93%
Androgen receptor binding	+	0.6658	66.58%
Thyroid receptor binding	+	0.5706	57.06%
Glucocorticoid receptor binding	+	0.5985	59.85%
Aromatase binding	-	0.5055	50.55%
PPAR gamma	+	0.7580	75.80%
Honey bee toxicity	-	0.7606	76.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.6396	63.96%

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	97.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.89%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.23%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.68%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.98%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.87%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.84%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.67%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	86.12%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	85.97%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.76%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.98%	95.56%
CHEMBL5028	O14672	ADAM10	82.70%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.40%	94.62%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.14%	89.44%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.03%	89.00%

Plants that contains it

• Adina eurhyncha
• Neonauclea sessilifolia
• Strychnos mellodora

Cross-Links

• PubChem: 21577866
• LOTUS: LTS0010081
• wikiData: Q104916414