2-[(2S,3R,4S)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid

Details

• Internal ID: 8738a3b7-5a7f-4bd9-95cb-5c28c7e6fc11
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[(2S,3R,4S)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=COC(C(C4CC(=O)O)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CO[C@H]([C@@H]([C@@H]4CC(=O)O)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C33H46O20/c1-4-12-13(6-20(36)37)15(9-47-30(12)52-32-26(42)24(40)22(38)18(7-34)50-32)29(45)49-17-5-14-16(28(44)46-3)10-48-31(21(14)11(17)2)53-33-27(43)25(41)23(39)19(8-35)51-33/h4,9-14,17-19,21-27,30-35,38-43H,1,5-8H2,2-3H3,(H,36,37)/t11-,12+,13-,14+,17-,18+,19+,21+,22+,23+,24-,25-,26+,27+,30-,31-,32-,33-/m0/s1
• InChI Key: ZWQKSBAPLOZUOM-HOLUWDGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₆O₂₀
• Molecular Weight: 762.70 g/mol
• Exact Mass: 762.25824385 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -3.65
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4701	47.01%
Caco-2	-	0.8860	88.60%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5826	58.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3552	35.52%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5667	56.67%
P-glycoprotein inhibitior	+	0.6438	64.38%
P-glycoprotein substrate	-	0.5216	52.16%
CYP3A4 substrate	+	0.6719	67.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8853	88.53%
CYP3A4 inhibition	-	0.8337	83.37%
CYP2C9 inhibition	-	0.9076	90.76%
CYP2C19 inhibition	-	0.8853	88.53%
CYP2D6 inhibition	-	0.9151	91.51%
CYP1A2 inhibition	-	0.8966	89.66%
CYP2C8 inhibition	+	0.6122	61.22%
CYP inhibitory promiscuity	-	0.9256	92.56%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7390	73.90%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9167	91.67%
Skin irritation	-	0.7317	73.17%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5424	54.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7751	77.51%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6716	67.16%
skin sensitisation	-	0.8536	85.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6784	67.84%
Acute Oral Toxicity (c)	III	0.5376	53.76%
Estrogen receptor binding	+	0.8005	80.05%
Androgen receptor binding	+	0.6337	63.37%
Thyroid receptor binding	-	0.5077	50.77%
Glucocorticoid receptor binding	+	0.5887	58.87%
Aromatase binding	-	0.4926	49.26%
PPAR gamma	+	0.6813	68.13%
Honey bee toxicity	-	0.7717	77.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7571	75.71%

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	98.15%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.69%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.53%	96.00%
CHEMBL2581	P07339	Cathepsin D	86.93%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.78%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.56%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.26%	94.73%
CHEMBL5028	O14672	ADAM10	86.08%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.09%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.59%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.24%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.75%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	81.68%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.66%	91.24%
CHEMBL5255	O00206	Toll-like receptor 4	80.28%	92.50%

Plants that contains it

• Strychnos axillaris

Cross-Links

• PubChem: 101844699
• LOTUS: LTS0267626
• wikiData: Q105385160