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

Details

• Internal ID: 0733f850-53c3-4c30-b61e-2ffa2ff686fc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7S,7aS)-7-hydroxy-5,7-dimethyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C18H28O10/c1-7-4-18(2,24)11-10(7)8(15(23)25-3)6-26-16(11)28-17-14(22)13(21)12(20)9(5-19)27-17/h6-7,9-14,16-17,19-22,24H,4-5H2,1-3H3/t7-,9-,10-,11-,12-,13+,14-,16+,17+,18+/m1/s1
• InChI Key: LKEDDJNDLLFHTN-FMBBYTRZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₁₀
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.16824709 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.76
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7126	71.26%
Caco-2	-	0.8135	81.35%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6065	60.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8039	80.39%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8857	88.57%
P-glycoprotein inhibitior	-	0.8188	81.88%
P-glycoprotein substrate	-	0.7490	74.90%
CYP3A4 substrate	+	0.6470	64.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.9139	91.39%
CYP2C9 inhibition	-	0.9219	92.19%
CYP2C19 inhibition	-	0.9009	90.09%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.9103	91.03%
CYP2C8 inhibition	-	0.7025	70.25%
CYP inhibitory promiscuity	-	0.8772	87.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6249	62.49%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9753	97.53%
Skin irritation	-	0.6947	69.47%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5666	56.66%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.8098	80.98%
skin sensitisation	-	0.8637	86.37%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4480	44.80%
Estrogen receptor binding	-	0.4755	47.55%
Androgen receptor binding	-	0.5257	52.57%
Thyroid receptor binding	-	0.5588	55.88%
Glucocorticoid receptor binding	-	0.6543	65.43%
Aromatase binding	-	0.5399	53.99%
PPAR gamma	-	0.5385	53.85%
Honey bee toxicity	-	0.7791	77.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.4412	44.12%

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	98.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL4208	P20618	Proteasome component C5	88.44%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.38%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.13%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.23%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	83.86%	92.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.39%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.77%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.69%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	80.50%	94.73%

Plants that contains it

• Pedicularis densispica

Cross-Links

• PubChem: 162877060
• LOTUS: LTS0172640
• wikiData: Q105153022