methyl (1S,4aS,5R,7aS)-5-butoxy-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: a9838c50-42ab-4bc1-af18-219132eed00d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7aS)-5-butoxy-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/C21H32O11/c1-3-4-5-29-12-6-10(7-22)14-15(12)11(19(27)28-2)9-30-20(14)32-21-18(26)17(25)16(24)13(8-23)31-21/h6,9,12-18,20-26H,3-5,7-8H2,1-2H3/t12-,13-,14-,15+,16-,17+,18-,20+,21+/m1/s1
• InChI Key: RYWUDXJHHMSWPB-SIWNXJGJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₁₁
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.19446183 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7179	71.79%
Caco-2	-	0.8103	81.03%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6771	67.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7410	74.10%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8874	88.74%
P-glycoprotein inhibitior	-	0.7396	73.96%
P-glycoprotein substrate	-	0.5991	59.91%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.9240	92.40%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.8252	82.52%
CYP2D6 inhibition	-	0.8845	88.45%
CYP1A2 inhibition	-	0.8335	83.35%
CYP2C8 inhibition	+	0.5348	53.48%
CYP inhibitory promiscuity	-	0.7473	74.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7112	71.12%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9515	95.15%
Skin irritation	-	0.7404	74.04%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4396	43.96%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8885	88.85%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6851	68.51%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.6040	60.40%
Androgen receptor binding	-	0.4871	48.71%
Thyroid receptor binding	-	0.5846	58.46%
Glucocorticoid receptor binding	-	0.4667	46.67%
Aromatase binding	+	0.5731	57.31%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8874	88.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7297	72.97%

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	97.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.41%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.10%	99.17%
CHEMBL2581	P07339	Cathepsin D	90.29%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.07%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.71%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.78%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	81.60%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.49%	86.33%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 102507166
• LOTUS: LTS0266144
• wikiData: Q105248187