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

Details

• Internal ID: 2bf8b36b-20b0-4a20-99c0-7fb1158af32b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C17H26O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,8-14,16-22H,3-6H2,1H3/t8-,9?,10-,11-,12-,13+,14-,16?,17+/m1/s1
• InChI Key: DKUJPZVAHYXRHF-HWQNNDOISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₀
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.15259702 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.50
• 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	-	0.5091	50.91%
Caco-2	-	0.8490	84.90%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7457	74.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9181	91.81%
P-glycoprotein inhibitior	-	0.9057	90.57%
P-glycoprotein substrate	-	0.7525	75.25%
CYP3A4 substrate	+	0.6156	61.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9461	94.61%
CYP2C9 inhibition	-	0.9247	92.47%
CYP2C19 inhibition	-	0.8362	83.62%
CYP2D6 inhibition	-	0.9099	90.99%
CYP1A2 inhibition	-	0.8761	87.61%
CYP2C8 inhibition	-	0.7789	77.89%
CYP inhibitory promiscuity	-	0.8138	81.38%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6806	68.06%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9688	96.88%
Skin irritation	-	0.7949	79.49%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7175	71.75%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8760	87.60%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5909	59.09%
Acute Oral Toxicity (c)	III	0.4685	46.85%
Estrogen receptor binding	+	0.5426	54.26%
Androgen receptor binding	+	0.6429	64.29%
Thyroid receptor binding	-	0.6118	61.18%
Glucocorticoid receptor binding	-	0.5737	57.37%
Aromatase binding	+	0.5281	52.81%
PPAR gamma	-	0.5938	59.38%
Honey bee toxicity	-	0.7674	76.74%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.7382	73.82%

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	97.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	85.91%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.29%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	84.98%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.59%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.18%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	82.77%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.14%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.23%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.00%	94.33%

Plants that contains it

• Phlomoides umbrosa

Cross-Links

• PubChem: 6325240
• NPASS: NPC159426