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

Details

• Internal ID: 4206f676-376e-4790-abc6-d17ff75423a9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3S,4R)-3-ethenyl-4-[[(2S,4S,6R)-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]oxan-2-yl]methyl]-2-[(2R,3S,4R,5R,6S)-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(CC(O2)CCC3=CC=C(C=C3)O)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]2C[C@H](C[C@H](O2)CCC3=CC=C(C=C3)O)O)C=C)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O
• InChI: InChI=1S/C29H40O12/c1-3-20-21(12-19-11-17(32)10-18(39-19)9-6-15-4-7-16(31)8-5-15)22(27(36)37-2)14-38-28(20)41-29-26(35)25(34)24(33)23(13-30)40-29/h3-5,7-8,14,17-21,23-26,28-35H,1,6,9-13H2,2H3/t17-,18+,19+,20-,21+,23-,24-,25+,26-,28-,29+/m0/s1
• InChI Key: SYCAAOWPYJBQKF-OYAFDOENSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₁₂
• Molecular Weight: 580.60 g/mol
• Exact Mass: 580.25197671 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.27
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5217	52.17%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8104	81.04%
OATP2B1 inhibitior	-	0.8660	86.60%
OATP1B1 inhibitior	+	0.7900	79.00%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8127	81.27%
P-glycoprotein inhibitior	-	0.5297	52.97%
P-glycoprotein substrate	+	0.5655	56.55%
CYP3A4 substrate	+	0.6919	69.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8544	85.44%
CYP3A4 inhibition	-	0.8050	80.50%
CYP2C9 inhibition	-	0.8851	88.51%
CYP2C19 inhibition	-	0.7244	72.44%
CYP2D6 inhibition	-	0.8495	84.95%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.8072	80.72%
CYP inhibitory promiscuity	-	0.8816	88.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7312	73.12%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9290	92.90%
Skin irritation	-	0.7909	79.09%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7545	75.45%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6967	69.67%
skin sensitisation	-	0.8078	80.78%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.6369	63.69%
Estrogen receptor binding	+	0.7883	78.83%
Androgen receptor binding	+	0.6556	65.56%
Thyroid receptor binding	-	0.5113	51.13%
Glucocorticoid receptor binding	+	0.6575	65.75%
Aromatase binding	+	0.5875	58.75%
PPAR gamma	+	0.6173	61.73%
Honey bee toxicity	-	0.6717	67.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.8846	88.46%

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	98.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.73%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.58%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.23%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	89.55%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.02%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.44%	94.45%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.41%	85.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.55%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	86.40%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.13%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.49%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.17%	96.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.12%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.65%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.97%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.12%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.11%	90.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.82%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.36%	96.90%

Plants that contains it

• Hydrangea chinensis
• Hydrangea macrophylla

Cross-Links

• PubChem: 154496749
• LOTUS: LTS0062237
• wikiData: Q105263484