[(1S,4aS,5R,7S,7aS)-1-[(2S,3S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-oxooxan-2-yl]oxy-4a,5-dihydroxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate

Details

• Internal ID: 72fdb3cf-f245-41ac-a09e-370d3f709222
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aS,5R,7S,7aS)-1-[(2S,3S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-oxooxan-2-yl]oxy-4a,5-dihydroxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate
• InChI: InChI=1S/C17H24O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-10,12-15,18,20-21,23-24H,5-6H2,1-2H3/t8-,9-,10-,12-,13-,14+,15+,16+,17-/m1/s1
• InChI Key: QLFIQFQWHOHGGW-MJKUXPPISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5102	51.02%
Caco-2	-	0.8706	87.06%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6456	64.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8637	86.37%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7526	75.26%
P-glycoprotein inhibitior	-	0.8247	82.47%
P-glycoprotein substrate	-	0.7339	73.39%
CYP3A4 substrate	+	0.6466	64.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8784	87.84%
CYP3A4 inhibition	-	0.8049	80.49%
CYP2C9 inhibition	-	0.9381	93.81%
CYP2C19 inhibition	-	0.9442	94.42%
CYP2D6 inhibition	-	0.9565	95.65%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	-	0.7491	74.91%
CYP inhibitory promiscuity	-	0.9323	93.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6285	62.85%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9561	95.61%
Skin irritation	-	0.7258	72.58%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7066	70.66%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5473	54.73%
skin sensitisation	-	0.8922	89.22%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7106	71.06%
Acute Oral Toxicity (c)	III	0.5492	54.92%
Estrogen receptor binding	+	0.7168	71.68%
Androgen receptor binding	+	0.6226	62.26%
Thyroid receptor binding	+	0.5720	57.20%
Glucocorticoid receptor binding	+	0.6306	63.06%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.5401	54.01%
Honey bee toxicity	-	0.8605	86.05%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.7110	71.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.66%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.91%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.48%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.39%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.34%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.53%	97.25%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.05%	97.28%
CHEMBL2581	P07339	Cathepsin D	83.31%	98.95%

Plants that contains it

• Caryopteris incana

Cross-Links

• PubChem: 100982868
• LOTUS: LTS0057843
• wikiData: Q105223541