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

Details

• Internal ID: 7c9e9561-7625-4ddb-a247-e44a7b738758
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(4aS,5R,7S)-4a,5-dihydroxy-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@]2(C1C(OC=C2)O[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC
• InChI: InChI=1S/C25H32O13/c1-24(38-17(29)6-4-12-3-5-13(27)14(9-12)34-2)10-16(28)25(33)7-8-35-23(21(24)25)37-22-20(32)19(31)18(30)15(11-26)36-22/h3-9,15-16,18-23,26-28,30-33H,10-11H2,1-2H3/b6-4+/t15-,16+,18-,19+,20-,21?,22+,23?,24-,25+/m0/s1
• InChI Key: XEAHABRMMIVTAK-VJHFJEQXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₃
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.18429107 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.49
• H-Bond Acceptor: 13
• 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	+	0.7567	75.67%
Caco-2	-	0.8924	89.24%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5174	51.74%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8742	87.42%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5072	50.72%
P-glycoprotein inhibitior	-	0.6221	62.21%
P-glycoprotein substrate	-	0.5902	59.02%
CYP3A4 substrate	+	0.6807	68.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.7980	79.80%
CYP2C9 inhibition	-	0.9250	92.50%
CYP2C19 inhibition	-	0.8799	87.99%
CYP2D6 inhibition	-	0.8572	85.72%
CYP1A2 inhibition	-	0.8165	81.65%
CYP2C8 inhibition	+	0.7335	73.35%
CYP inhibitory promiscuity	-	0.8378	83.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5976	59.76%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9416	94.16%
Skin irritation	-	0.7681	76.81%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7364	73.64%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.7717	77.17%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8550	85.50%
Acute Oral Toxicity (c)	III	0.5478	54.78%
Estrogen receptor binding	+	0.7892	78.92%
Androgen receptor binding	+	0.6797	67.97%
Thyroid receptor binding	+	0.6356	63.56%
Glucocorticoid receptor binding	+	0.6922	69.22%
Aromatase binding	+	0.6516	65.16%
PPAR gamma	+	0.7121	71.21%
Honey bee toxicity	-	0.7980	79.80%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.8121	81.21%

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	99.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.66%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.29%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.11%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.25%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.79%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.28%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.34%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.94%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.99%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.88%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.01%	96.21%
CHEMBL3194	P02766	Transthyretin	84.89%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.46%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.06%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.72%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.71%	95.89%

Plants that contains it

• Harpagophytum procumbens
• Scrophularia ningpoensis

Cross-Links

• PubChem: 24893235
• NPASS: NPC244601