methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: a0a0553a-3511-4c7c-9365-cbba02d2fec5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)COC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C\C5=CC=C(C=C5)O)O)O)O)O)O)O
• InChI: InChI=1S/C32H40O17/c1-43-29(42)18-11-45-30(22-15(10-33)5-8-17(18)22)49-32-28(41)26(39)24(37)20(48-32)13-46-31-27(40)25(38)23(36)19(47-31)12-44-21(35)9-4-14-2-6-16(34)7-3-14/h2-7,9,11,17,19-20,22-28,30-34,36-41H,8,10,12-13H2,1H3/b9-4-/t17-,19-,20-,22-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1
• InChI Key: QIWWLKDHHMGRQL-SKMDTYRSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₁₇
• Molecular Weight: 696.60 g/mol
• Exact Mass: 696.22654980 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.43
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6367	63.67%
Caco-2	-	0.8931	89.31%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7156	71.56%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8091	80.91%
OATP1B3 inhibitior	+	0.9711	97.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4842	48.42%
P-glycoprotein inhibitior	-	0.4304	43.04%
P-glycoprotein substrate	-	0.5097	50.97%
CYP3A4 substrate	+	0.6902	69.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8916	89.16%
CYP2C9 inhibition	-	0.8823	88.23%
CYP2C19 inhibition	-	0.7339	73.39%
CYP2D6 inhibition	-	0.8899	88.99%
CYP1A2 inhibition	-	0.8398	83.98%
CYP2C8 inhibition	+	0.7704	77.04%
CYP inhibitory promiscuity	-	0.7701	77.01%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6237	62.37%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.8038	80.38%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7012	70.12%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8391	83.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6867	68.67%
Acute Oral Toxicity (c)	III	0.5120	51.20%
Estrogen receptor binding	+	0.7879	78.79%
Androgen receptor binding	+	0.6666	66.66%
Thyroid receptor binding	-	0.5249	52.49%
Glucocorticoid receptor binding	+	0.6516	65.16%
Aromatase binding	+	0.5841	58.41%
PPAR gamma	+	0.6938	69.38%
Honey bee toxicity	-	0.7715	77.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9330	93.30%

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	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.07%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.84%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.90%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.87%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.61%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.84%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	88.43%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	87.81%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	85.48%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	84.69%	91.49%
CHEMBL2581	P07339	Cathepsin D	84.60%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.50%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.87%	95.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.14%	95.89%

Plants that contains it

• Gardenia jasminoides
• Ziziphus jujuba

Cross-Links

• PubChem: 10842393
• NPASS: NPC294881