(2E,6E)-3,7-Dimethyl-2,6-octadiene-1,8-diol 1-[[(1S)-1alpha-(beta-D-glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydro-7alpha-hydroxy-7beta-methylcyclopenta[c]pyran]-4-carboxylate]8-[[(1S)-1alpha-(beta-D-glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydro-6alpha-hydroxy-7-methylenecyclopenta[c]pyran]-4-carboxylate]

Details

• Internal ID: a2d59162-9215-4580-8580-5c4e6582d79e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2E,6E)-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-dimethylocta-2,6-dienyl] (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(=CCOC(=O)C1=COC(C2C1CCC2(C)O)OC3C(C(C(C(O3)CO)O)O)O)CCC=C(C)COC(=O)C4=COC(C5C4CC(C5=C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C/C(=C\COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC[C@]2(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)/CC/C=C(\C)/COC(=O)C4=CO[C@H]([C@H]5[C@@H]4C[C@@H](C5=C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C42H60O20/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/h7,9,16-17,21-22,25-35,38-41,43-51,54H,3,5-6,8,10-15H2,1-2,4H3/b18-9+,19-7+/t21-,22-,25+,26-,27-,28-,29-,30-,31-,32+,33+,34-,35-,38+,39+,40+,41+,42+/m1/s1
• InChI Key: JLXHTCVHBYWAHE-XPBCPRNJSA-N
• Popularity: 0 references 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: -1.20
• Atomic LogP (AlogP): -1.81
• 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	-	0.8654	86.54%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7734	77.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7838	78.38%
OATP1B3 inhibitior	+	0.8845	88.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6298	62.98%
BSEP inhibitior	+	0.8197	81.97%
P-glycoprotein inhibitior	+	0.7431	74.31%
P-glycoprotein substrate	+	0.5335	53.35%
CYP3A4 substrate	+	0.7249	72.49%
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	+	0.7418	74.18%
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	-	0.9043	90.43%
Skin irritation	+	0.5458	54.58%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6871	68.71%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7236	72.36%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7831	78.31%
Acute Oral Toxicity (c)	I	0.4943	49.43%
Estrogen receptor binding	+	0.8086	80.86%
Androgen receptor binding	+	0.7449	74.49%
Thyroid receptor binding	+	0.5661	56.61%
Glucocorticoid receptor binding	+	0.7495	74.95%
Aromatase binding	+	0.6844	68.44%
PPAR gamma	+	0.7919	79.19%
Honey bee toxicity	-	0.6462	64.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
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	97.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.03%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.08%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.56%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.05%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.03%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.28%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.66%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.01%	91.19%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	85.54%	92.50%
CHEMBL1937	Q92769	Histone deacetylase 2	84.67%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.56%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.46%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.91%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.83%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.09%	90.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.02%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	80.26%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	80.26%	97.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.23%	92.94%

Plants that contains it

• Achillea millefolium
• Premna odorata

Cross-Links

• PubChem: 101006165
• NPASS: NPC270204
• LOTUS: LTS0022567
• wikiData: Q105131178