7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-[(6-hydroxy-2,6-dimethylocta-2,7-dienoyl)oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 3cb423f8-33e2-418b-b59f-46f5e07a8488
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-[(6-hydroxy-2,6-dimethylocta-2,7-dienoyl)oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC(=CCCC(C)(C=C)O)C(=O)OCC1C(C(C(C(O1)OC2C3C(CCC3(C)O)C(=CO2)C(=O)O)O)O)O
• SMILES (Isomeric): CC(=CCCC(C)(C=C)O)C(=O)OCC1C(C(C(C(O1)OC2C3C(CCC3(C)O)C(=CO2)C(=O)O)O)O)O
• InChI: InChI=1S/C26H38O12/c1-5-25(3,33)9-6-7-13(2)22(32)35-12-16-18(27)19(28)20(29)24(37-16)38-23-17-14(8-10-26(17,4)34)15(11-36-23)21(30)31/h5,7,11,14,16-20,23-24,27-29,33-34H,1,6,8-10,12H2,2-4H3,(H,30,31)
• InChI Key: AXRQCSKKDBKXEL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₁₂
• Molecular Weight: 542.60 g/mol
• Exact Mass: 542.23632664 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.12
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7558	75.58%
Caco-2	-	0.8544	85.44%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7205	72.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7576	75.76%
OATP1B3 inhibitior	+	0.8989	89.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7079	70.79%
BSEP inhibitior	+	0.7060	70.60%
P-glycoprotein inhibitior	-	0.4386	43.86%
P-glycoprotein substrate	-	0.6266	62.66%
CYP3A4 substrate	+	0.7046	70.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.7987	79.87%
CYP2C9 inhibition	-	0.8572	85.72%
CYP2C19 inhibition	-	0.9145	91.45%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.9011	90.11%
CYP2C8 inhibition	+	0.7088	70.88%
CYP inhibitory promiscuity	-	0.9248	92.48%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6461	64.61%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9415	94.15%
Skin irritation	+	0.5596	55.96%
Skin corrosion	-	0.9154	91.54%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4635	46.35%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5463	54.63%
skin sensitisation	-	0.8810	88.10%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6843	68.43%
Acute Oral Toxicity (c)	III	0.5469	54.69%
Estrogen receptor binding	+	0.8049	80.49%
Androgen receptor binding	+	0.5901	59.01%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6786	67.86%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.5807	58.07%
Honey bee toxicity	-	0.7560	75.60%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9457	94.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.11%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.41%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.53%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.78%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.62%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.73%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	88.66%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	87.45%	92.50%
CHEMBL5028	O14672	ADAM10	86.41%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.80%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.43%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.53%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.40%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.81%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.07%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.03%	96.95%
CHEMBL2581	P07339	Cathepsin D	81.71%	98.95%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.68%	90.93%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.38%	96.90%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.81%	93.04%
CHEMBL4208	P20618	Proteasome component C5	80.13%	90.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.02%	85.00%

Plants that contains it

• Veronica bellidioides

Cross-Links

• PubChem: 74095038
• LOTUS: LTS0180560
• wikiData: Q104920730