[(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-phenylprop-2-enoate

Details

• Internal ID: 4402f7a9-33f0-4f88-8b96-81059a0149c6
• 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-phenylprop-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=CC=C5)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=CC=C5)O
• InChI: InChI=1S/C30H38O14/c1-14-22(34)27(43-20(33)8-7-15-5-3-2-4-6-15)26(38)30(40-14)41-18-11-16(12-31)21-17(18)9-10-39-28(21)44-29-25(37)24(36)23(35)19(13-32)42-29/h2-11,14,17-19,21-32,34-38H,12-13H2,1H3/b8-7+/t14-,17-,18+,19+,21+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1
• InChI Key: RUFZYMSKBXORQX-JXXSAGFBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₄
• Molecular Weight: 622.60 g/mol
• Exact Mass: 622.22615588 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5575	55.75%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7025	70.25%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8054	80.54%
OATP1B3 inhibitior	+	0.9660	96.60%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6019	60.19%
P-glycoprotein inhibitior	-	0.5254	52.54%
P-glycoprotein substrate	-	0.5545	55.45%
CYP3A4 substrate	+	0.6552	65.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.9510	95.10%
CYP2C9 inhibition	-	0.8827	88.27%
CYP2C19 inhibition	-	0.7887	78.87%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	-	0.8349	83.49%
CYP2C8 inhibition	+	0.6564	65.64%
CYP inhibitory promiscuity	-	0.5586	55.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6603	66.03%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9266	92.66%
Skin irritation	-	0.8065	80.65%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6491	64.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7796	77.96%
Micronuclear	-	0.6341	63.41%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8344	83.44%
Acute Oral Toxicity (c)	III	0.5052	50.52%
Estrogen receptor binding	+	0.7842	78.42%
Androgen receptor binding	+	0.5464	54.64%
Thyroid receptor binding	+	0.5151	51.51%
Glucocorticoid receptor binding	+	0.5869	58.69%
Aromatase binding	-	0.5060	50.60%
PPAR gamma	+	0.6418	64.18%
Honey bee toxicity	-	0.7374	73.74%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.7507	75.07%

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	98.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.19%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.79%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.43%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.92%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.54%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.80%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.10%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.20%	97.36%
CHEMBL5028	O14672	ADAM10	84.73%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.15%	90.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.83%	91.71%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	82.58%	88.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.92%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.11%	99.17%

Plants that contains it

• Verbascum nigrum

Cross-Links

• PubChem: 21591414
• LOTUS: LTS0249993
• wikiData: Q105245591