(2S)-2-[2-[(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]ethylamino]-3-phenylpropanoic acid

Details

• Internal ID: 53342af7-bfa7-451e-a293-b2c5b84ef6d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S)-2-[2-[(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]ethylamino]-3-phenylpropanoic acid
• SMILES (Canonical): COC(=O)C1=COC(C(C1CCNC(CC2=CC=CC=C2)C(=O)O)C=C)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CCN[C@@H](CC2=CC=CC=C2)C(=O)O)C=C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C26H35NO11/c1-3-15-16(9-10-27-18(23(32)33)11-14-7-5-4-6-8-14)17(24(34)35-2)13-36-25(15)38-26-22(31)21(30)20(29)19(12-28)37-26/h3-8,13,15-16,18-22,25-31H,1,9-12H2,2H3,(H,32,33)/t15-,16+,18+,19-,20-,21+,22-,25+,26+/m1/s1
• InChI Key: IEDHINQMIRRVDA-DBXUSRIBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₅NO₁₁
• Molecular Weight: 537.60 g/mol
• Exact Mass: 537.22101093 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -0.69
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8299	82.99%
Caco-2	-	0.8937	89.37%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6353	63.53%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.7785	77.85%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.9220	92.20%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5719	57.19%
P-glycoprotein inhibitior	-	0.5296	52.96%
P-glycoprotein substrate	-	0.5397	53.97%
CYP3A4 substrate	+	0.6580	65.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8481	84.81%
CYP3A4 inhibition	-	0.9204	92.04%
CYP2C9 inhibition	-	0.8831	88.31%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.7508	75.08%
CYP1A2 inhibition	-	0.8473	84.73%
CYP2C8 inhibition	+	0.6556	65.56%
CYP inhibitory promiscuity	-	0.9599	95.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6605	66.05%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9519	95.19%
Skin irritation	-	0.7690	76.90%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7224	72.24%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7698	76.98%
skin sensitisation	-	0.8522	85.22%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5285	52.85%
Acute Oral Toxicity (c)	III	0.6233	62.33%
Estrogen receptor binding	+	0.7551	75.51%
Androgen receptor binding	+	0.6275	62.75%
Thyroid receptor binding	-	0.5239	52.39%
Glucocorticoid receptor binding	+	0.5619	56.19%
Aromatase binding	-	0.5276	52.76%
PPAR gamma	+	0.6366	63.66%
Honey bee toxicity	-	0.6955	69.55%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4373	43.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.71%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.95%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.31%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.86%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.44%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	90.41%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.10%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.27%	97.14%
CHEMBL5028	O14672	ADAM10	83.53%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.08%	95.83%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	81.35%	87.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.11%	94.23%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 101189142
• NPASS: NPC220011
• LOTUS: LTS0100816
• wikiData: Q105111712