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

Details

• Internal ID: 586377cf-3ebe-4409-a7c9-5954aa76ed07
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C19H30O9/c1-2-3-5-25-12-7-10(8-20)14-11(12)4-6-26-18(14)28-19-17(24)16(23)15(22)13(9-21)27-19/h4,6-7,11-24H,2-3,5,8-9H2,1H3/t11-,12-,13+,14+,15+,16-,17+,18-,19-/m0/s1
• InChI Key: YNUMHOSLFIVVNZ-NRKZWZSVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₉
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.18898253 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.98
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6406	64.06%
Caco-2	-	0.7944	79.44%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5831	58.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7995	79.95%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.8194	81.94%
P-glycoprotein substrate	-	0.6845	68.45%
CYP3A4 substrate	+	0.6038	60.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.9371	93.71%
CYP2C9 inhibition	-	0.8461	84.61%
CYP2C19 inhibition	-	0.7721	77.21%
CYP2D6 inhibition	-	0.8788	87.88%
CYP1A2 inhibition	-	0.7724	77.24%
CYP2C8 inhibition	+	0.4934	49.34%
CYP inhibitory promiscuity	-	0.6494	64.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6565	65.65%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9620	96.20%
Skin irritation	-	0.7396	73.96%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4389	43.89%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8916	89.16%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5039	50.39%
Estrogen receptor binding	+	0.5728	57.28%
Androgen receptor binding	-	0.5452	54.52%
Thyroid receptor binding	-	0.5296	52.96%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6703	67.03%
PPAR gamma	+	0.5711	57.11%
Honey bee toxicity	-	0.8800	88.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6104	61.04%
Fish aquatic toxicity	+	0.7572	75.72%

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	96.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.83%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.36%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.99%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.66%	98.95%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.47%	80.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.29%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	84.07%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.79%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.82%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.68%	93.56%

Plants that contains it

• Pedicularis chinensis

Cross-Links

• PubChem: 101931838
• LOTUS: LTS0017559
• wikiData: Q105351118