3-[7-hydroxy-4-methoxycarbonyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-7-carbonyl]oxy-2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

Details

• Internal ID: 3d58f68f-4fe9-4f99-9a94-9ea95f1c65f4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 3-[7-hydroxy-4-methoxycarbonyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-7-carbonyl]oxy-2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=COC(=O)C2(C=CC3C2C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)O)C(=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=COC(=O)C2(C=CC3C2C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)O)C(=O)O)O
• InChI: InChI=1S/C27H30O16/c1-38-16-7-11(3-4-15(16)29)13(22(33)34)9-41-26(36)27(37)6-5-12-14(23(35)39-2)10-40-24(18(12)27)43-25-21(32)20(31)19(30)17(8-28)42-25/h3-7,9-10,12,17-21,24-25,28-32,37H,8H2,1-2H3,(H,33,34)
• InChI Key: CLSONMZJGDJYSR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.87
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7193	71.93%
Caco-2	-	0.9087	90.87%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5959	59.59%
OATP2B1 inhibitior	-	0.5764	57.64%
OATP1B1 inhibitior	+	0.7730	77.30%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7060	70.60%
P-glycoprotein inhibitior	-	0.4337	43.37%
P-glycoprotein substrate	+	0.5332	53.32%
CYP3A4 substrate	+	0.6754	67.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.8434	84.34%
CYP2C9 inhibition	-	0.7582	75.82%
CYP2C19 inhibition	-	0.7158	71.58%
CYP2D6 inhibition	-	0.8859	88.59%
CYP1A2 inhibition	-	0.7978	79.78%
CYP2C8 inhibition	+	0.7934	79.34%
CYP inhibitory promiscuity	-	0.6700	67.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6616	66.16%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9141	91.41%
Skin irritation	-	0.7679	76.79%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6748	67.48%
Micronuclear	+	0.5733	57.33%
Hepatotoxicity	-	0.6341	63.41%
skin sensitisation	-	0.8116	81.16%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6082	60.82%
Acute Oral Toxicity (c)	III	0.4538	45.38%
Estrogen receptor binding	+	0.7925	79.25%
Androgen receptor binding	+	0.6657	66.57%
Thyroid receptor binding	+	0.5927	59.27%
Glucocorticoid receptor binding	+	0.6521	65.21%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7000	70.00%
Honey bee toxicity	-	0.7729	77.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6966	69.66%
Fish aquatic toxicity	+	0.8701	87.01%

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	99.34%	91.11%
CHEMBL4208	P20618	Proteasome component C5	95.78%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.36%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.14%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.33%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.20%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.89%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.75%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	87.61%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.29%	95.89%
CHEMBL3194	P02766	Transthyretin	86.61%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	85.96%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.27%	96.90%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.39%	91.07%
CHEMBL2581	P07339	Cathepsin D	83.78%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.85%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	80.65%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.35%	95.56%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 73088338
• LOTUS: LTS0185346
• wikiData: Q104963890