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

Details

• Internal ID: 1eb9c2d8-ea88-482b-aea6-e2cc5c5df48a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl acetate
• InChI: InChI=1S/C17H24O10/c1-7(19)25-6-8-4-10(20)9-2-3-24-16(12(8)9)27-17-15(23)14(22)13(21)11(5-18)26-17/h2-4,9-18,20-23H,5-6H2,1H3/t9-,10+,11+,12+,13+,14-,15+,16-,17-/m0/s1
• InChI Key: NTXYRYAVOMIMPH-QHDSNVNLSA-N
• Popularity: 2 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	+	0.6066	60.66%
Caco-2	-	0.8990	89.90%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6935	69.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8277	82.77%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7490	74.90%
P-glycoprotein inhibitior	-	0.8493	84.93%
P-glycoprotein substrate	-	0.8516	85.16%
CYP3A4 substrate	+	0.5957	59.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.9718	97.18%
CYP2C9 inhibition	-	0.9176	91.76%
CYP2C19 inhibition	-	0.8668	86.68%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.8531	85.31%
CYP2C8 inhibition	-	0.7109	71.09%
CYP inhibitory promiscuity	-	0.7219	72.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7257	72.57%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9668	96.68%
Skin irritation	-	0.7769	77.69%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.6491	64.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.6037	60.37%
Micronuclear	-	0.7841	78.41%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8887	88.87%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7967	79.67%
Acute Oral Toxicity (c)	III	0.4285	42.85%
Estrogen receptor binding	+	0.5670	56.70%
Androgen receptor binding	-	0.5233	52.33%
Thyroid receptor binding	-	0.5959	59.59%
Glucocorticoid receptor binding	-	0.6606	66.06%
Aromatase binding	+	0.5545	55.45%
PPAR gamma	-	0.5751	57.51%
Honey bee toxicity	-	0.7928	79.28%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7705	77.05%
Fish aquatic toxicity	+	0.6938	69.38%

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	96.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.75%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.05%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.11%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.96%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.94%	95.56%
CHEMBL2581	P07339	Cathepsin D	80.27%	98.95%

Plants that contains it

• Plantago loeflingii

Cross-Links

• PubChem: 101085814
• LOTUS: LTS0027120
• wikiData: Q105185742