[(1S,4aR,5S,6R,7S,7aS)-5,6,7-trihydroxy-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-7-yl]methyl (E)-3-phenylprop-2-enoate

Details

• Internal ID: b0e76699-5c20-47f7-99f3-85e63d1d130b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5S,6R,7S,7aS)-5,6,7-trihydroxy-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-7-yl]methyl (E)-3-phenylprop-2-enoate
• SMILES (Canonical): C1=CC=C(C=C1)C=CC(=O)OCC2(C3C(C=COC3OC4C(C(C(C(O4)CO)O)O)O)C(C2O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)/C=C/C(=O)OC[C@]2([C@@H]3[C@@H](C=CO[C@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@@H]([C@H]2O)O)O
• InChI: InChI=1S/C24H30O12/c25-10-14-18(28)19(29)20(30)23(35-14)36-22-16-13(8-9-33-22)17(27)21(31)24(16,32)11-34-15(26)7-6-12-4-2-1-3-5-12/h1-9,13-14,16-23,25,27-32H,10-11H2/b7-6+/t13-,14-,16-,17+,18-,19+,20-,21-,22+,23+,24-/m1/s1
• InChI Key: NRCZKVGMFVNDIY-JJWUYXHRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₂
• Molecular Weight: 510.50 g/mol
• Exact Mass: 510.17372639 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5504	55.04%
Caco-2	-	0.8906	89.06%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5737	57.37%
OATP2B1 inhibitior	-	0.8491	84.91%
OATP1B1 inhibitior	+	0.8251	82.51%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5079	50.79%
P-glycoprotein inhibitior	-	0.6529	65.29%
P-glycoprotein substrate	-	0.7602	76.02%
CYP3A4 substrate	+	0.6242	62.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.9316	93.16%
CYP2C9 inhibition	-	0.9558	95.58%
CYP2C19 inhibition	-	0.8504	85.04%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	-	0.9195	91.95%
CYP2C8 inhibition	+	0.6566	65.66%
CYP inhibitory promiscuity	-	0.8850	88.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6047	60.47%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9474	94.74%
Skin irritation	-	0.8009	80.09%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5464	54.64%
Micronuclear	-	0.6041	60.41%
Hepatotoxicity	-	0.7657	76.57%
skin sensitisation	-	0.8500	85.00%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6538	65.38%
Acute Oral Toxicity (c)	III	0.4807	48.07%
Estrogen receptor binding	+	0.6620	66.20%
Androgen receptor binding	+	0.5795	57.95%
Thyroid receptor binding	-	0.5282	52.82%
Glucocorticoid receptor binding	-	0.5777	57.77%
Aromatase binding	+	0.6605	66.05%
PPAR gamma	+	0.6867	68.67%
Honey bee toxicity	-	0.7557	75.57%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	-	0.4400	44.00%

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	98.27%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.47%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.74%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.60%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	94.17%	90.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	92.98%	94.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.88%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.98%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.11%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.87%	89.00%
CHEMBL5028	O14672	ADAM10	83.79%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.92%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.01%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.75%	100.00%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.21%	88.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.23%	99.17%

Plants that contains it

• Globularia alypum

Cross-Links

• PubChem: 21603204
• LOTUS: LTS0181238
• wikiData: Q105184437