ethyl (1S,4aS,5R,7aS)-5-hydroxy-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-4-carboxylate

Details

• Internal ID: ac8e3970-8ab9-4fff-89ed-be6a05c0449c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: ethyl (1S,4aS,5R,7aS)-5-hydroxy-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-4-carboxylate
• InChI: InChI=1S/C18H26O11/c1-2-26-16(25)8-6-27-17(11-7(4-19)3-9(21)12(8)11)29-18-15(24)14(23)13(22)10(5-20)28-18/h3,6,9-15,17-24H,2,4-5H2,1H3/t9-,10-,11-,12+,13-,14+,15-,17+,18+/m1/s1
• InChI Key: PIFFAIMSAYMMCE-FUIAOSIISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₁₁
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.14751164 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -2.87
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6266	62.66%
Caco-2	-	0.8746	87.46%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6799	67.99%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.7687	76.87%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9095	90.95%
P-glycoprotein inhibitior	-	0.8848	88.48%
P-glycoprotein substrate	-	0.8670	86.70%
CYP3A4 substrate	+	0.5849	58.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.9575	95.75%
CYP2C9 inhibition	-	0.8784	87.84%
CYP2C19 inhibition	-	0.7959	79.59%
CYP2D6 inhibition	-	0.9173	91.73%
CYP1A2 inhibition	-	0.8485	84.85%
CYP2C8 inhibition	-	0.7153	71.53%
CYP inhibitory promiscuity	-	0.6184	61.84%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6833	68.33%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9483	94.83%
Skin irritation	-	0.7917	79.17%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5910	59.10%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8797	87.97%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6313	63.13%
Acute Oral Toxicity (c)	III	0.4904	49.04%
Estrogen receptor binding	+	0.6212	62.12%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6295	62.95%
Glucocorticoid receptor binding	-	0.6005	60.05%
Aromatase binding	+	0.5662	56.62%
PPAR gamma	-	0.6354	63.54%
Honey bee toxicity	-	0.8186	81.86%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7505	75.05%
Fish aquatic toxicity	-	0.3779	37.79%

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	94.74%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.06%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	84.79%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.57%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.54%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.58%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.26%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.83%	95.56%
CHEMBL2581	P07339	Cathepsin D	80.39%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162909521
• LOTUS: LTS0263251
• wikiData: Q105209470