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

Details

• Internal ID: d8f8dfdb-e2c1-4ca9-b851-d44af0cdb856
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2S,6R)-8-[(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-2,6-dimethyloctyl] (1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-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(C)COC(=O)C1=COC(C2C1CC(C2=C)O)OC3C(C(C(C(O3)CO)O)O)O)CCOC(=O)C4=COC(C5C4CCC5(C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@H](CCC[C@H](C)COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@@H](C2=C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CCOC(=O)C4=CO[C@H]([C@H]5[C@@H]4CC[C@]5(C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C42H64O20/c1-18(9-11-55-36(52)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)6-5-7-19(2)15-56-37(53)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/h16-19,21-22,25-35,38-41,43-51,54H,3,5-15H2,1-2,4H3/t18-,19+,21-,22-,25+,26-,27-,28-,29-,30-,31-,32+,33+,34-,35-,38+,39+,40+,41+,42+/m1/s1
• InChI Key: ACZFDOMPWNLLHA-CIBBSCMUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₂₀
• Molecular Weight: 888.90 g/mol
• Exact Mass: 888.39909443 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 17

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	-	0.8665	86.65%
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	+	0.7925	79.25%
OATP1B3 inhibitior	+	0.8845	88.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6298	62.98%
BSEP inhibitior	+	0.8247	82.47%
P-glycoprotein inhibitior	+	0.7426	74.26%
P-glycoprotein substrate	+	0.5878	58.78%
CYP3A4 substrate	+	0.7265	72.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8740	87.40%
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	+	0.6158	61.58%
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	-	0.9044	90.44%
Skin irritation	+	0.5458	54.58%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7297	72.97%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7750	77.50%
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	+	0.6466	64.66%
Acute Oral Toxicity (c)	I	0.4943	49.43%
Estrogen receptor binding	+	0.8243	82.43%
Androgen receptor binding	+	0.7414	74.14%
Thyroid receptor binding	+	0.5369	53.69%
Glucocorticoid receptor binding	+	0.7552	75.52%
Aromatase binding	+	0.6909	69.09%
PPAR gamma	+	0.7657	76.57%
Honey bee toxicity	-	0.7427	74.27%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.67%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.22%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.37%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	93.56%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.16%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.69%	96.21%
CHEMBL2581	P07339	Cathepsin D	90.12%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.89%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	89.66%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.51%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.11%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	87.86%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.94%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.74%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.11%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	85.81%	92.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.72%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.36%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.63%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.39%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.96%	92.94%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.78%	96.90%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.50%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.21%	86.33%
CHEMBL2514	O95665	Neurotensin receptor 2	81.16%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.03%	92.88%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.97%	94.97%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.46%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	80.42%	94.75%

Plants that contains it

• Premna odorata

Cross-Links

• PubChem: 162912824
• LOTUS: LTS0055237
• wikiData: Q104909422