(4S,5E,6S)-5-ethylidene-4-[2-[(1S,2R,3S,4S)-3-[[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxymethyl]-4-[(2S)-1-hydroxypropan-2-yl]-2-methylcyclopentyl]oxy-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid

Details

• Internal ID: a8347c64-937e-42ab-8c62-e0b40519c3b1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4S,5E,6S)-5-ethylidene-4-[2-[(1S,2R,3S,4S)-3-[[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxymethyl]-4-[(2S)-1-hydroxypropan-2-yl]-2-methylcyclopentyl]oxy-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCC3C(C(CC3C(C)CO)OC(=O)CC4C(=COC(C4=CC)OC5C(C(C(C(O5)CO)O)O)O)C(=O)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]3[C@H](C)CO)OC(=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)O)C
• InChI: InChI=1S/C43H62O23/c1-6-19-22(25(38(55)56)15-60-40(19)65-42-36(53)34(51)32(49)28(12-45)63-42)10-31(48)62-27-8-21(17(3)11-44)24(18(27)4)14-59-30(47)9-23-20(7-2)41(61-16-26(23)39(57)58-5)66-43-37(54)35(52)33(50)29(13-46)64-43/h6-7,15-18,21-24,27-29,32-37,40-46,49-54H,8-14H2,1-5H3,(H,55,56)/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: GCVHEYYKXYZLNQ-QRCWDEGMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₂O₂₃
• Molecular Weight: 946.90 g/mol
• Exact Mass: 946.36818822 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.38
• H-Bond Acceptor: 22
• H-Bond Donor: 10
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6425	64.25%
Caco-2	-	0.8679	86.79%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7953	79.53%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.7227	72.27%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9174	91.74%
P-glycoprotein inhibitior	+	0.7378	73.78%
P-glycoprotein substrate	+	0.6329	63.29%
CYP3A4 substrate	+	0.6850	68.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8907	89.07%
CYP3A4 inhibition	-	0.8532	85.32%
CYP2C9 inhibition	-	0.8960	89.60%
CYP2C19 inhibition	-	0.8687	86.87%
CYP2D6 inhibition	-	0.9237	92.37%
CYP1A2 inhibition	-	0.8951	89.51%
CYP2C8 inhibition	+	0.6531	65.31%
CYP inhibitory promiscuity	-	0.9299	92.99%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7158	71.58%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.7666	76.66%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	+	0.5223	52.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6947	69.47%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7477	74.77%
skin sensitisation	-	0.9046	90.46%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6615	66.15%
Acute Oral Toxicity (c)	III	0.5273	52.73%
Estrogen receptor binding	+	0.8028	80.28%
Androgen receptor binding	+	0.6886	68.86%
Thyroid receptor binding	+	0.5473	54.73%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.5627	56.27%
PPAR gamma	+	0.7774	77.74%
Honey bee toxicity	-	0.7030	70.30%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9428	94.28%

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	98.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.88%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.63%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.74%	86.33%
CHEMBL5028	O14672	ADAM10	87.24%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	87.14%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.27%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.23%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.91%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.72%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.36%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	85.18%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	84.79%	91.19%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.64%	97.53%
CHEMBL5255	O00206	Toll-like receptor 4	81.36%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.63%	95.83%

Plants that contains it

• Jasminum nudiflorum

Cross-Links

• PubChem: 162973281
• LOTUS: LTS0244913
• wikiData: Q105006492