Methyl 7-(benzoyloxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: e1e6bd29-e098-412c-b313-a27dabafb65d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-(benzoyloxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C24H28O11/c1-31-22(30)15-11-33-23(35-24-20(28)19(27)18(26)16(9-25)34-24)17-13(7-8-14(15)17)10-32-21(29)12-5-3-2-4-6-12/h2-7,11,14,16-20,23-28H,8-10H2,1H3
• InChI Key: PXHQKPVBAUDOSK-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₁
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.16316171 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.36
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.8837	88.37%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7427	74.27%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.8134	81.34%
OATP1B3 inhibitior	+	0.9703	97.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7070	70.70%
P-glycoprotein inhibitior	-	0.5554	55.54%
P-glycoprotein substrate	-	0.7075	70.75%
CYP3A4 substrate	+	0.6368	63.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.9266	92.66%
CYP2C9 inhibition	-	0.8979	89.79%
CYP2C19 inhibition	-	0.7860	78.60%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8544	85.44%
CYP2C8 inhibition	+	0.6673	66.73%
CYP inhibitory promiscuity	-	0.8238	82.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6634	66.34%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9530	95.30%
Skin irritation	-	0.8121	81.21%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.6737	67.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3638	36.38%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.7823	78.23%
skin sensitisation	-	0.8637	86.37%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7874	78.74%
Acute Oral Toxicity (c)	III	0.4913	49.13%
Estrogen receptor binding	+	0.8196	81.96%
Androgen receptor binding	+	0.6360	63.60%
Thyroid receptor binding	-	0.5576	55.76%
Glucocorticoid receptor binding	+	0.6093	60.93%
Aromatase binding	-	0.5187	51.87%
PPAR gamma	+	0.6687	66.87%
Honey bee toxicity	-	0.8171	81.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9036	90.36%

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	95.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.96%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.20%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.59%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.49%	94.73%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.28%	97.09%
CHEMBL5028	O14672	ADAM10	85.82%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.94%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.74%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	82.39%	90.17%
CHEMBL4208	P20618	Proteasome component C5	81.27%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.12%	95.83%

Plants that contains it

• Oldenlandia corymbosa

Cross-Links

• PubChem: 73324203
• LOTUS: LTS0245320
• wikiData: Q105216189