2-[3-ethenyl-5-methoxycarbonyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethyl 6-[2-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 2e3f276b-77f7-47eb-9b12-80f90e9a8881
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[3-ethenyl-5-methoxycarbonyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethyl 6-[2-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OCCC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): CC1C(CC2C1C(OC=C2C(=O)OCCC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)O
• InChI: InChI=1S/C46H62O27/c1-4-17-18(21(39(60)63-3)14-65-42(17)72-45-37(58)34(55)31(52)26(12-48)70-45)8-9-64-40(61)22-15-66-43(73-46-38(59)35(56)32(53)27(13-49)71-46)28-16(2)24(10-20(22)28)67-41(62)19-6-5-7-23(29(19)50)68-44-36(57)33(54)30(51)25(11-47)69-44/h4-7,14-18,20,24-28,30-38,42-59H,1,8-13H2,2-3H3
• InChI Key: ZZEMLPUURHSGBP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₂O₂₇
• Molecular Weight: 1047.00 g/mol
• Exact Mass: 1046.34784670 g/mol
• Topological Polar Surface Area (TPSA): 416.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -4.99
• H-Bond Acceptor: 27
• H-Bond Donor: 13
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6234	62.34%
Caco-2	-	0.8699	86.99%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6525	65.25%
OATP2B1 inhibitior	-	0.8660	86.60%
OATP1B1 inhibitior	+	0.7483	74.83%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9373	93.73%
P-glycoprotein inhibitior	+	0.7343	73.43%
P-glycoprotein substrate	+	0.6999	69.99%
CYP3A4 substrate	+	0.7274	72.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.8875	88.75%
CYP2C9 inhibition	-	0.7809	78.09%
CYP2C19 inhibition	-	0.7188	71.88%
CYP2D6 inhibition	-	0.8881	88.81%
CYP1A2 inhibition	-	0.7177	71.77%
CYP2C8 inhibition	+	0.8281	82.81%
CYP inhibitory promiscuity	-	0.7629	76.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7354	73.54%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.7659	76.59%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7497	74.97%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5483	54.83%
Acute Oral Toxicity (c)	III	0.4961	49.61%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6892	68.92%
Thyroid receptor binding	+	0.6137	61.37%
Glucocorticoid receptor binding	+	0.7395	73.95%
Aromatase binding	+	0.5502	55.02%
PPAR gamma	+	0.8016	80.16%
Honey bee toxicity	-	0.6986	69.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9340	93.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.42%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.34%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.30%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.65%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.36%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	87.23%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.53%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	86.26%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	84.88%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.46%	99.17%
CHEMBL5028	O14672	ADAM10	84.15%	97.50%
CHEMBL3891	P07384	Calpain 1	83.25%	93.04%
CHEMBL4530	P00488	Coagulation factor XIII	83.16%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.67%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.77%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.51%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.44%	90.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.72%	82.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.31%	94.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.00%	89.62%

Plants that contains it

• Gentiana depressa

Cross-Links

• PubChem: 162926433
• LOTUS: LTS0100794
• wikiData: Q105386744