[8-[7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-3,7-dimethylocta-3,7-dienyl] 6-hydroxy-7-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 2444593d-1f8c-461f-87fa-f0d10dbac705
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [8-[7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-3,7-dimethylocta-3,7-dienyl] 6-hydroxy-7-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=CCCC(=COC(=O)C1=COC(C2C1CCC2(C)O)OC3C(C(C(C(O3)CO)O)O)O)C)CCOC(=O)C4=COC(C5C4CC(C5=C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC(=CCCC(=COC(=O)C1=COC(C2C1CCC2(C)O)OC3C(C(C(C(O3)CO)O)O)O)C)CCOC(=O)C4=COC(C5C4CC(C5=C)O)OC6C(C(C(C(O6)CO)O)O)O
• InChI: InChI=1S/C42H60O20/c1-18(9-11-55-36(52)24-17-57-38(28-20(3)25(45)12-22(24)28)61-40-34(50)32(48)30(46)26(13-43)59-40)6-5-7-19(2)15-56-37(53)23-16-58-39(29-21(23)8-10-42(29,4)54)62-41-35(51)33(49)31(47)27(14-44)60-41/h6,15-17,21-22,25-35,38-41,43-51,54H,3,5,7-14H2,1-2,4H3
• InChI Key: JKRLDDRTCWKVQS-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₀O₂₀
• Molecular Weight: 884.90 g/mol
• Exact Mass: 884.36779430 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6584	65.84%
Caco-2	-	0.8666	86.66%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7734	77.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7797	77.97%
OATP1B3 inhibitior	+	0.8845	88.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6298	62.98%
BSEP inhibitior	+	0.8004	80.04%
P-glycoprotein inhibitior	+	0.7425	74.25%
P-glycoprotein substrate	+	0.5670	56.70%
CYP3A4 substrate	+	0.7277	72.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8712	87.12%
CYP3A4 inhibition	-	0.8497	84.97%
CYP2C9 inhibition	-	0.9019	90.19%
CYP2C19 inhibition	-	0.9180	91.80%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.9138	91.38%
CYP2C8 inhibition	+	0.7277	72.77%
CYP inhibitory promiscuity	-	0.9681	96.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6641	66.41%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9047	90.47%
Skin irritation	+	0.5458	54.58%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7462	74.62%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6736	67.36%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7937	79.37%
Acute Oral Toxicity (c)	I	0.4943	49.43%
Estrogen receptor binding	+	0.7998	79.98%
Androgen receptor binding	+	0.7496	74.96%
Thyroid receptor binding	+	0.5832	58.32%
Glucocorticoid receptor binding	+	0.7621	76.21%
Aromatase binding	+	0.6610	66.10%
PPAR gamma	+	0.8072	80.72%
Honey bee toxicity	-	0.6560	65.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9713	97.13%

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	98.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.20%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.79%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.20%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.11%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.38%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.21%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.63%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.93%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.79%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.62%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.08%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.05%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.82%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.01%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.50%	97.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.46%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.23%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.22%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	83.11%	97.79%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.32%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	82.16%	94.73%
CHEMBL2581	P07339	Cathepsin D	82.03%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.60%	90.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.92%	96.90%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.62%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.55%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.49%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.14%	90.00%

Plants that contains it

• Premna odorata

Cross-Links

• PubChem: 162912883
• LOTUS: LTS0137104
• wikiData: Q105130496