methyl (4S,5E,6S)-5-ethylidene-4-[2-[(2S)-2-[(1R,7S,8E,9S,14S,15S,17R)-8-ethylidene-17-methyl-3,11-dioxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6,12-trioxatricyclo[12.2.1.04,9]heptadec-4-en-15-yl]propoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: fb5a22fa-6cf3-4b92-8340-1c5ce293c07f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[(2S)-2-[(1R,7S,8E,9S,14S,15S,17R)-8-ethylidene-17-methyl-3,11-dioxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6,12-trioxatricyclo[12.2.1.04,9]heptadec-4-en-15-yl]propoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C2CC(=O)OCC3C(C(CC3C(C)COC(=O)CC4C(=COC(C4=CC)OC5C(C(C(C(O5)CO)O)O)O)C(=O)OC)OC(=O)C2=COC1OC6C(C(C(C(O6)CO)O)O)O)C
• SMILES (Isomeric): C/C=C/1\[C@@H]2CC(=O)OC[C@@H]3[C@H]([C@@H](C[C@H]3[C@H](C)COC(=O)C[C@@H]\4C(=CO[C@H](/C4=C/C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C(=O)OC)OC(=O)C2=CO[C@H]1O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C
• InChI: InChI=1S/C43H60O22/c1-6-19-22(25(38(54)56-5)15-59-40(19)64-42-36(52)34(50)32(48)28(11-44)62-42)9-30(46)57-13-17(3)21-8-27-18(4)24(21)14-58-31(47)10-23-20(7-2)41(60-16-26(23)39(55)61-27)65-43-37(53)35(51)33(49)29(12-45)63-43/h6-7,15-18,21-24,27-29,32-37,40-45,48-53H,8-14H2,1-5H3/b19-6+,20-7+/t17-,18-,21+,22+,23+,24-,27-,28-,29-,32-,33-,34+,35+,36-,37-,40+,41+,42+,43+/m1/s1
• InChI Key: GZBCQRQJJVIXDD-XNKWJWSISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₀O₂₂
• Molecular Weight: 928.90 g/mol
• Exact Mass: 928.35762354 g/mol
• Topological Polar Surface Area (TPSA): 322.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.90
• H-Bond Acceptor: 22
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7074	70.74%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7593	75.93%
OATP1B3 inhibitior	+	0.9182	91.82%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8806	88.06%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	+	0.7366	73.66%
CYP3A4 substrate	+	0.7155	71.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.8445	84.45%
CYP2C9 inhibition	-	0.9220	92.20%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8717	87.17%
CYP2C8 inhibition	+	0.6978	69.78%
CYP inhibitory promiscuity	-	0.9365	93.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9032	90.32%
Skin irritation	-	0.6980	69.80%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	+	0.5668	56.68%
Human Ether-a-go-go-Related Gene inhibition	+	0.7594	75.94%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9033	90.33%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6149	61.49%
Acute Oral Toxicity (c)	III	0.4985	49.85%
Estrogen receptor binding	+	0.7781	77.81%
Androgen receptor binding	+	0.6995	69.95%
Thyroid receptor binding	+	0.5538	55.38%
Glucocorticoid receptor binding	+	0.7740	77.40%
Aromatase binding	+	0.5561	55.61%
PPAR gamma	+	0.7803	78.03%
Honey bee toxicity	-	0.6232	62.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9561	95.61%

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	97.46%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.38%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.27%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.19%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	90.57%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.48%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.89%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.65%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.00%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.40%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.27%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.31%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.41%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	83.89%	97.79%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.76%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	82.29%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.80%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.73%	94.73%

Plants that contains it

• Jasminum mesnyi

Cross-Links

• PubChem: 162892705
• LOTUS: LTS0260291
• wikiData: Q105024317