[(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7R,7aR)-4-formyl-4a-hydroxy-7-methyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: c11ef2a8-fb87-4ebc-94f5-6a321870f01f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7R,7aR)-4-formyl-4a-hydroxy-7-methyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1CCC2(C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=C(C=C4)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@@H]1[C@@H](OC=C2C=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C/C4=CC=C(C=C4)O)O
• InChI: InChI=1S/C25H30O11/c1-13-8-9-25(32)15(10-26)12-33-23(19(13)25)36-24-22(21(31)20(30)17(11-27)34-24)35-18(29)7-4-14-2-5-16(28)6-3-14/h2-7,10,12-13,17,19-24,27-28,30-32H,8-9,11H2,1H3/b7-4+/t13-,17-,19+,20-,21+,22-,23+,24+,25+/m1/s1
• InChI Key: GNTMWOQKWXXPHF-SZSBDVJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₁
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.17881177 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8275	82.75%
Caco-2	-	0.8783	87.83%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7306	73.06%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.7660	76.60%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7651	76.51%
BSEP inhibitior	+	0.6619	66.19%
P-glycoprotein inhibitior	-	0.5368	53.68%
P-glycoprotein substrate	-	0.5735	57.35%
CYP3A4 substrate	+	0.6874	68.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.8157	81.57%
CYP2C19 inhibition	-	0.8532	85.32%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.7887	78.87%
CYP2C8 inhibition	+	0.7062	70.62%
CYP inhibitory promiscuity	-	0.8459	84.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5793	57.93%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.6258	62.58%
Skin corrosion	-	0.9276	92.76%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6567	65.67%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.8732	87.32%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8647	86.47%
Acute Oral Toxicity (c)	I	0.4504	45.04%
Estrogen receptor binding	+	0.7303	73.03%
Androgen receptor binding	+	0.7018	70.18%
Thyroid receptor binding	+	0.5892	58.92%
Glucocorticoid receptor binding	+	0.6481	64.81%
Aromatase binding	+	0.5863	58.63%
PPAR gamma	+	0.6279	62.79%
Honey bee toxicity	-	0.7958	79.58%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9345	93.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.73%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.45%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.56%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.26%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.74%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.11%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.94%	100.00%
CHEMBL4208	P20618	Proteasome component C5	86.77%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.68%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	86.66%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	85.35%	92.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.33%	89.67%
CHEMBL206	P03372	Estrogen receptor alpha	83.75%	97.64%
CHEMBL242	Q92731	Estrogen receptor beta	83.42%	98.35%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.28%	94.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.23%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.02%	85.00%
CHEMBL3194	P02766	Transthyretin	81.76%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.37%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.34%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.32%	94.80%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.14%	94.08%

Plants that contains it

• Baccharis latifolia
• Calea szyszylowiczii
• Clibadium armanii
• Geraea canescens
• Liatris acidota
• Ligularia fischeri
• Ligularia veitchiana
• Morithamnus crassus
• Ophryosporus heptanthus
• Ophryosporus lorentzii
• Penstemon eximius
• Penstemon parryi
• Pojarkovia pojarkovae
• Tagetes erecta
• Tussilago farfara
• Xenophyllum ciliolatum

Cross-Links

• PubChem: 101677404
• LOTUS: LTS0006835
• wikiData: Q104995303