methyl (4S,5Z,6S)-4-[2-[[(1S,2R,3R,5S)-5-[1-[2-[(2S,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]acetyl]oxypropan-2-yl]-3-hydroxy-2-methylcyclopentyl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: ae6c6544-4335-4db8-845c-549bc3c88388
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5Z,6S)-4-[2-[[(1S,2R,3R,5S)-5-[1-[2-[(2S,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]acetyl]oxypropan-2-yl]-3-hydroxy-2-methylcyclopentyl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCC3C(C(CC3C(C)COC(=O)CC4C(C(OC=C4C(=O)OC)OC5C(C(C(C(O5)CO)O)O)O)C=C)O)C
• SMILES (Isomeric): C/C=C\1/[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OC[C@@H]3[C@H]([C@@H](C[C@H]3C(C)COC(=O)C[C@H]4C([C@@H](OC=C4C(=O)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=C)O)C
• InChI: InChI=1S/C44H64O23/c1-7-20-23(26(39(56)58-5)16-62-41(20)66-43-37(54)35(52)33(50)29(12-45)64-43)10-31(48)60-14-18(3)22-9-28(47)19(4)25(22)15-61-32(49)11-24-21(8-2)42(63-17-27(24)40(57)59-6)67-44-38(55)36(53)34(51)30(13-46)65-44/h7-8,16-20,22-25,28-30,33-38,41-47,50-55H,1,9-15H2,2-6H3/b21-8-/t18?,19-,20?,22+,23+,24+,25-,28-,29-,30-,33-,34-,35+,36+,37-,38-,41+,42+,43+,44+/m1/s1
• InChI Key: OATMJDBYGOZZPL-LGKRPLJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₄O₂₃
• Molecular Weight: 961.00 g/mol
• Exact Mass: 960.38383828 g/mol
• Topological Polar Surface Area (TPSA): 343.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.44
• H-Bond Acceptor: 23
• H-Bond Donor: 9
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6121	61.21%
Caco-2	-	0.8645	86.45%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7333	73.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7195	71.95%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9469	94.69%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.7194	71.94%
CYP3A4 substrate	+	0.7126	71.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.6778	67.78%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.8637	86.37%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.8990	89.90%
CYP2C8 inhibition	+	0.7028	70.28%
CYP inhibitory promiscuity	-	0.9664	96.64%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7394	73.94%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9017	90.17%
Skin irritation	-	0.7202	72.02%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7646	76.46%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6352	63.52%
skin sensitisation	-	0.8856	88.56%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7397	73.97%
Acute Oral Toxicity (c)	III	0.5436	54.36%
Estrogen receptor binding	+	0.7968	79.68%
Androgen receptor binding	+	0.7086	70.86%
Thyroid receptor binding	+	0.5687	56.87%
Glucocorticoid receptor binding	+	0.7649	76.49%
Aromatase binding	+	0.5480	54.80%
PPAR gamma	+	0.7956	79.56%
Honey bee toxicity	-	0.6523	65.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9573	95.73%

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	98.43%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.79%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.08%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.69%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.37%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	90.37%	97.79%
CHEMBL220	P22303	Acetylcholinesterase	90.21%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	89.67%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.50%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.38%	89.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.25%	85.31%
CHEMBL226	P30542	Adenosine A1 receptor	87.98%	95.93%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.11%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.80%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.35%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.25%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	85.68%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.53%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.44%	97.53%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.27%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.10%	96.61%
CHEMBL5028	O14672	ADAM10	84.71%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.16%	86.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.49%	80.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.85%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.71%	95.89%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.26%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.00%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.74%	97.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.41%	95.17%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.55%	95.71%

Plants that contains it

• Jasminum urophyllum

Cross-Links

• PubChem: 101937092
• LOTUS: LTS0150483
• wikiData: Q105188801