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

Details

• Internal ID: 022f42fe-287a-4959-9ba9-38c942f9ab67
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl] acetate
• InChI: InChI=1S/C17H24O10/c1-7(20)25-10-4-8(5-18)12-9(10)2-3-24-16(12)27-17-15(23)14(22)13(21)11(6-19)26-17/h2-4,9-19,21-23H,5-6H2,1H3/t9-,10+,11+,12+,13+,14-,15+,16-,17-/m0/s1
• InChI Key: DSSROTZNBIUOAZ-QHDSNVNLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.23
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5120	51.20%
Caco-2	-	0.8862	88.62%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7177	71.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7993	79.93%
OATP1B3 inhibitior	+	0.9650	96.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7926	79.26%
P-glycoprotein inhibitior	-	0.8687	86.87%
P-glycoprotein substrate	-	0.8168	81.68%
CYP3A4 substrate	+	0.5935	59.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.9604	96.04%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.8556	85.56%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	-	0.8797	87.97%
CYP2C8 inhibition	-	0.7427	74.27%
CYP inhibitory promiscuity	-	0.6799	67.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6850	68.50%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9711	97.11%
Skin irritation	-	0.8021	80.21%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.5991	59.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7315	73.15%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.8199	81.99%
skin sensitisation	-	0.8848	88.48%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6481	64.81%
Acute Oral Toxicity (c)	III	0.4307	43.07%
Estrogen receptor binding	+	0.5335	53.35%
Androgen receptor binding	-	0.6004	60.04%
Thyroid receptor binding	-	0.5556	55.56%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6223	62.23%
PPAR gamma	+	0.5359	53.59%
Honey bee toxicity	-	0.7632	76.32%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6905	69.05%
Fish aquatic toxicity	-	0.4601	46.01%

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	96.43%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.22%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.35%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.93%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.46%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.85%	99.17%

Plants that contains it

• Pedicularis condensata

Cross-Links

• PubChem: 11143582
• LOTUS: LTS0179847
• wikiData: Q104987998