[(1S,2R,4S,5R,6S,10S)-6-hydroxy-2-methyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 1371ff90-a443-48d6-b00b-bb7d25bde192
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,2R,4S,5R,6S,10S)-6-hydroxy-2-methyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)OC3C4C(O4)(C5C3(C=COC5OC6C(C(C(C(O6)CO)O)O)O)O)C)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O[C@@H]3[C@H]4[C@](O4)([C@@H]5[C@]3(C=CO[C@H]5O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O
• InChI: InChI=1S/C31H44O19/c1-29(41)4-3-10-11(9-44-25(14(10)29)48-26-19(38)17(36)15(34)12(7-32)45-26)24(40)47-23-22-30(2,50-22)21-28(43-6-5-31(21,23)42)49-27-20(39)18(37)16(35)13(8-33)46-27/h5-6,9-10,12-23,25-28,32-39,41-42H,3-4,7-8H2,1-2H3/t10-,12-,13-,14-,15-,16-,17+,18+,19-,20-,21-,22+,23-,25+,26+,27+,28+,29+,30-,31+/m1/s1
• InChI Key: FDHKIHNRBMODHH-ZHOGSEEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₉
• Molecular Weight: 720.70 g/mol
• Exact Mass: 720.24767917 g/mol
• Topological Polar Surface Area (TPSA): 297.00 Ų
• XlogP: -4.40
• Atomic LogP (AlogP): -5.06
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6840	68.40%
Caco-2	-	0.8886	88.86%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6928	69.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7615	76.15%
OATP1B3 inhibitior	+	0.9233	92.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7629	76.29%
BSEP inhibitior	-	0.6230	62.30%
P-glycoprotein inhibitior	+	0.6449	64.49%
P-glycoprotein substrate	-	0.5769	57.69%
CYP3A4 substrate	+	0.7020	70.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.9248	92.48%
CYP2C9 inhibition	-	0.8487	84.87%
CYP2C19 inhibition	-	0.8853	88.53%
CYP2D6 inhibition	-	0.9097	90.97%
CYP1A2 inhibition	-	0.8596	85.96%
CYP2C8 inhibition	+	0.6504	65.04%
CYP inhibitory promiscuity	-	0.9056	90.56%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9205	92.05%
Skin irritation	-	0.6231	62.31%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7720	77.20%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8573	85.73%
skin sensitisation	-	0.8705	87.05%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7236	72.36%
Acute Oral Toxicity (c)	I	0.5527	55.27%
Estrogen receptor binding	+	0.7810	78.10%
Androgen receptor binding	+	0.7247	72.47%
Thyroid receptor binding	-	0.5277	52.77%
Glucocorticoid receptor binding	+	0.5917	59.17%
Aromatase binding	+	0.5882	58.82%
PPAR gamma	+	0.6934	69.34%
Honey bee toxicity	-	0.7799	77.99%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7319	73.19%

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	97.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.50%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.76%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.55%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.91%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.47%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.59%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	88.34%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.60%	91.24%
CHEMBL5255	O00206	Toll-like receptor 4	85.96%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.72%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.10%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.05%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.82%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.45%	95.83%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.95%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.91%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.71%	86.92%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.59%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	80.50%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.10%	100.00%

Plants that contains it

• Kickxia elatine

Cross-Links

• PubChem: 163074293
• LOTUS: LTS0064229
• wikiData: Q104993588