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

Details

• Internal ID: 1cdd649e-4fd3-48de-ad3f-347aa998accf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 5-hydroxy-7-[(4-hydroxybenzoyl)oxymethyl]-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C24H28O13/c1-33-22(32)13-9-35-23(37-24-20(30)19(29)18(28)15(7-25)36-24)16-11(6-14(27)17(13)16)8-34-21(31)10-2-4-12(26)5-3-10/h2-6,9,14-20,23-30H,7-8H2,1H3
• InChI Key: HKMDXFWRIFPDKR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₃
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.15299094 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5850	58.50%
Caco-2	-	0.9182	91.82%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6140	61.40%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.7485	74.85%
OATP1B3 inhibitior	+	0.9747	97.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4768	47.68%
P-glycoprotein inhibitior	-	0.6102	61.02%
P-glycoprotein substrate	-	0.6414	64.14%
CYP3A4 substrate	+	0.6282	62.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.8157	81.57%
CYP2C19 inhibition	-	0.7410	74.10%
CYP2D6 inhibition	-	0.8971	89.71%
CYP1A2 inhibition	-	0.8714	87.14%
CYP2C8 inhibition	+	0.7120	71.20%
CYP inhibitory promiscuity	-	0.6656	66.56%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5909	59.09%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.7977	79.77%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4730	47.30%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8367	83.67%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7836	78.36%
Acute Oral Toxicity (c)	III	0.5724	57.24%
Estrogen receptor binding	+	0.7852	78.52%
Androgen receptor binding	+	0.6597	65.97%
Thyroid receptor binding	-	0.5051	50.51%
Glucocorticoid receptor binding	+	0.5633	56.33%
Aromatase binding	-	0.5440	54.40%
PPAR gamma	+	0.6714	67.14%
Honey bee toxicity	-	0.8019	80.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	+	0.7724	77.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	93.93%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.07%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.82%	86.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	89.48%	85.00%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.38%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.38%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.34%	97.09%
CHEMBL4208	P20618	Proteasome component C5	80.10%	90.00%

Plants that contains it

• Oldenlandia corymbosa

Cross-Links

• PubChem: 163032787
• LOTUS: LTS0011019
• wikiData: Q105029763