methyl (2S,3R,4S)-3-ethenyl-4-[[(2S,6R)-6-(4-hydroxyphenyl)-4-oxooxan-2-yl]methyl]-2-[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: 126077f3-22d2-4536-8247-fbc4303cb0d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-4-[[(2S,6R)-6-(4-hydroxyphenyl)-4-oxooxan-2-yl]methyl]-2-[(2R,3S,4R,5R,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(C1CC2CC(=O)CC(O2)C3=CC=C(C=C3)O)C=C)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2CC(=O)C[C@@H](O2)C3=CC=C(C=C3)O)C=C)O[C@@H]4[C@H]([C@@H]([C@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C27H34O12/c1-3-17-18(10-16-8-15(30)9-20(37-16)13-4-6-14(29)7-5-13)19(25(34)35-2)12-36-26(17)39-27-24(33)23(32)22(31)21(11-28)38-27/h3-7,12,16-18,20-24,26-29,31-33H,1,8-11H2,2H3/t16-,17-,18+,20-,21-,22+,23-,24+,26+,27-/m1/s1
• InChI Key: CWRAQHOZLCMDKY-IFYZXCKLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₂
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.20502652 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.22
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5830	58.30%
Caco-2	-	0.8945	89.45%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7531	75.31%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.7572	75.72%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5262	52.62%
P-glycoprotein inhibitior	-	0.5688	56.88%
P-glycoprotein substrate	-	0.5684	56.84%
CYP3A4 substrate	+	0.6817	68.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8646	86.46%
CYP2C9 inhibition	-	0.7747	77.47%
CYP2C19 inhibition	-	0.7973	79.73%
CYP2D6 inhibition	-	0.9234	92.34%
CYP1A2 inhibition	-	0.8864	88.64%
CYP2C8 inhibition	+	0.6793	67.93%
CYP inhibitory promiscuity	-	0.7735	77.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7297	72.97%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9324	93.24%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7481	74.81%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.6998	69.98%
skin sensitisation	-	0.8369	83.69%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6676	66.76%
Acute Oral Toxicity (c)	III	0.6016	60.16%
Estrogen receptor binding	+	0.7879	78.79%
Androgen receptor binding	+	0.6383	63.83%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6070	60.70%
Aromatase binding	-	0.4890	48.90%
PPAR gamma	+	0.7041	70.41%
Honey bee toxicity	-	0.7611	76.11%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9358	93.58%

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	99.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.54%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.85%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	90.14%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.69%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	88.58%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.10%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.78%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.00%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.19%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.04%	86.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.54%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.28%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.95%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	81.43%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.17%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.89%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.24%	90.93%

Plants that contains it

• Hydrangea chinensis

Cross-Links

• PubChem: 101759623
• LOTUS: LTS0155302
• wikiData: Q104971470