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

Details

• Internal ID: 15da34a1-f3c4-4cfd-ac7d-320d55fa23b9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,7aR)-4a,6-dihydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,7a-dihydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C17H22O12/c1-5-8-15(29-16-12(22)11(21)10(20)7(3-18)28-16)27-4-6(14(24)26-2)17(8,25)13(23)9(5)19/h4,7-8,10-12,15-16,18-22,25H,3H2,1-2H3/t7-,8+,10-,11+,12-,15+,16+,17+/m1/s1
• InChI Key: STHQIPXYCDNWIY-ONLDKOTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₁₂
• Molecular Weight: 418.30 g/mol
• Exact Mass: 418.11112613 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -3.02
• H-Bond Acceptor: 12
• 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	+	0.5530	55.30%
Caco-2	-	0.8585	85.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7235	72.35%
OATP2B1 inhibitior	-	0.8514	85.14%
OATP1B1 inhibitior	+	0.7712	77.12%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6979	69.79%
P-glycoprotein inhibitior	-	0.8399	83.99%
P-glycoprotein substrate	-	0.7856	78.56%
CYP3A4 substrate	+	0.6416	64.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.9105	91.05%
CYP2C9 inhibition	-	0.9033	90.33%
CYP2C19 inhibition	-	0.8981	89.81%
CYP2D6 inhibition	-	0.9280	92.80%
CYP1A2 inhibition	-	0.9220	92.20%
CYP2C8 inhibition	+	0.4702	47.02%
CYP inhibitory promiscuity	-	0.8275	82.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6586	65.86%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9347	93.47%
Skin irritation	-	0.7445	74.45%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7050	70.50%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.6699	66.99%
skin sensitisation	-	0.8605	86.05%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4596	45.96%
Estrogen receptor binding	+	0.5517	55.17%
Androgen receptor binding	+	0.5353	53.53%
Thyroid receptor binding	-	0.5725	57.25%
Glucocorticoid receptor binding	+	0.5844	58.44%
Aromatase binding	+	0.5870	58.70%
PPAR gamma	-	0.5754	57.54%
Honey bee toxicity	-	0.7936	79.36%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.4378	43.78%

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	98.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.15%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.63%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.14%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.08%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.07%	86.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.87%	96.90%
CHEMBL4040	P28482	MAP kinase ERK2	82.49%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.67%	89.00%

Plants that contains it

• Verbena officinalis

Cross-Links

• PubChem: 101875572
• NPASS: NPC112498