[(2R,3R,4R,5S,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 1846d9ff-cd05-460d-bf2e-3e523e366731
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2R,3R,4R,5S,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C=C(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)CO)O)OC(=O)C=CC5=CC(=C(C=C5)OC)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2C=C([C@@H]3[C@H]2C=CO[C@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)O)OC(=O)/C=C/C5=CC(=C(C=C5)OC)O)O
• InChI: InChI=1S/C31H40O16/c1-13-23(36)28(46-21(35)6-4-14-3-5-18(41-2)17(34)9-14)27(40)31(43-13)44-19-10-15(11-32)22-16(19)7-8-42-29(22)47-30-26(39)25(38)24(37)20(12-33)45-30/h3-10,13,16,19-20,22-34,36-40H,11-12H2,1-2H3/b6-4+/t13-,16-,19+,20+,22+,23-,24+,25-,26+,27+,28+,29-,30-,31-/m0/s1
• InChI Key: BMOKZWFNXYQOGE-REKXUBECSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₆
• Molecular Weight: 668.60 g/mol
• Exact Mass: 668.23163518 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.97
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6784	67.84%
Caco-2	-	0.8847	88.47%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5787	57.87%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8276	82.76%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6473	64.73%
P-glycoprotein inhibitior	-	0.4601	46.01%
P-glycoprotein substrate	+	0.5990	59.90%
CYP3A4 substrate	+	0.6817	68.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8699	86.99%
CYP2C9 inhibition	-	0.8350	83.50%
CYP2C19 inhibition	-	0.6454	64.54%
CYP2D6 inhibition	-	0.8471	84.71%
CYP1A2 inhibition	-	0.8311	83.11%
CYP2C8 inhibition	+	0.7318	73.18%
CYP inhibitory promiscuity	+	0.5231	52.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6980	69.80%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.8010	80.10%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7406	74.06%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8067	80.67%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8947	89.47%
Acute Oral Toxicity (c)	III	0.5747	57.47%
Estrogen receptor binding	+	0.7669	76.69%
Androgen receptor binding	-	0.4890	48.90%
Thyroid receptor binding	+	0.5152	51.52%
Glucocorticoid receptor binding	+	0.6315	63.15%
Aromatase binding	-	0.5183	51.83%
PPAR gamma	+	0.6599	65.99%
Honey bee toxicity	-	0.7109	71.09%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.7948	79.48%

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	99.46%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.92%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.90%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.96%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.96%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.48%	91.49%
CHEMBL3194	P02766	Transthyretin	89.12%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.77%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.95%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.66%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.18%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.90%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.71%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.78%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	81.55%	94.73%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.63%	98.00%
CHEMBL4208	P20618	Proteasome component C5	80.49%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.07%	97.09%

Plants that contains it

• Verbascum nigrum

Cross-Links

• PubChem: 44715578
• LOTUS: LTS0182914
• wikiData: Q104938473