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

Details

• Internal ID: 233ccbf9-64a4-4432-8d52-5be5c424cef2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (1S,6S,7S,7aS)-6,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C17H24O11/c1-17(24)9(19)3-6-7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h3,5,8-13,15-16,18-22,24H,4H2,1-2H3/t8-,9+,10-,11-,12+,13-,15+,16+,17-/m1/s1
• InChI Key: KSQVTHWVSWYGNQ-OANLTPPESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.12
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6867	68.67%
Caco-2	-	0.8478	84.78%
Blood Brain Barrier	-	0.6892	68.92%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7520	75.20%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.7978	79.78%
OATP1B3 inhibitior	+	0.9373	93.73%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9541	95.41%
P-glycoprotein inhibitior	-	0.8702	87.02%
P-glycoprotein substrate	-	0.7653	76.53%
CYP3A4 substrate	+	0.6520	65.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.9248	92.48%
CYP2C9 inhibition	-	0.9050	90.50%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.8964	89.64%
CYP1A2 inhibition	-	0.8825	88.25%
CYP2C8 inhibition	-	0.5642	56.42%
CYP inhibitory promiscuity	-	0.7574	75.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6360	63.60%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.7305	73.05%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5852	58.52%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8547	85.47%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5366	53.66%
Acute Oral Toxicity (c)	III	0.4552	45.52%
Estrogen receptor binding	+	0.5687	56.87%
Androgen receptor binding	-	0.4936	49.36%
Thyroid receptor binding	-	0.5171	51.71%
Glucocorticoid receptor binding	-	0.4778	47.78%
Aromatase binding	+	0.5919	59.19%
PPAR gamma	+	0.5222	52.22%
Honey bee toxicity	-	0.8527	85.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.5000	50.00%

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	97.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.64%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.17%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.87%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.73%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.37%	86.33%
CHEMBL4208	P20618	Proteasome component C5	82.16%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.18%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.05%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.44%	91.24%

Plants that contains it

• Gentiana lutea

Cross-Links

• PubChem: 101324899
• NPASS: NPC4553