methyl (1R,4aR,7R,7aR)-7-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 3cd4a805-2f07-4e58-8d84-52e48848450d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1R,4aR,7R,7aR)-7-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CCC2COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@@H]([C@@H]2[C@H]1CC[C@H]2COC(=O)/C=C\C3=CC=C(C=C3)O)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O
• InChI: InChI=1S/C26H32O12/c1-34-24(33)17-12-36-25(38-26-23(32)22(31)21(30)18(10-27)37-26)20-14(5-8-16(17)20)11-35-19(29)9-4-13-2-6-15(28)7-3-13/h2-4,6-7,9,12,14,16,18,20-23,25-28,30-32H,5,8,10-11H2,1H3/b9-4-/t14-,16-,18-,20-,21-,22+,23-,25+,26+/m0/s1
• InChI Key: COQOXCPEJJIULA-HENKLDSMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.18
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6016	60.16%
Caco-2	-	0.8884	88.84%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.7997	79.97%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.7616	76.16%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7550	75.50%
P-glycoprotein inhibitior	-	0.5647	56.47%
P-glycoprotein substrate	-	0.5983	59.83%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.9301	93.01%
CYP2C9 inhibition	-	0.8879	88.79%
CYP2C19 inhibition	-	0.7232	72.32%
CYP2D6 inhibition	-	0.8644	86.44%
CYP1A2 inhibition	-	0.7062	70.62%
CYP2C8 inhibition	+	0.7583	75.83%
CYP inhibitory promiscuity	-	0.8118	81.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6198	61.98%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9469	94.69%
Skin irritation	-	0.8030	80.30%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.6340	63.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8203	82.03%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7478	74.78%
skin sensitisation	-	0.8567	85.67%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6144	61.44%
Acute Oral Toxicity (c)	III	0.4868	48.68%
Estrogen receptor binding	+	0.8043	80.43%
Androgen receptor binding	+	0.6942	69.42%
Thyroid receptor binding	-	0.5278	52.78%
Glucocorticoid receptor binding	-	0.4748	47.48%
Aromatase binding	+	0.5414	54.14%
PPAR gamma	+	0.6843	68.43%
Honey bee toxicity	-	0.8305	83.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9002	90.02%

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	98.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.36%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.78%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.39%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.19%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.25%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	90.45%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.41%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.01%	95.83%
CHEMBL5255	O00206	Toll-like receptor 4	87.68%	92.50%
CHEMBL2581	P07339	Cathepsin D	87.36%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.31%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.27%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.61%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.39%	86.92%
CHEMBL4208	P20618	Proteasome component C5	84.00%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.40%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.96%	95.89%

Plants that contains it

• Viburnum luzonicum

Cross-Links

• PubChem: 163186434
• LOTUS: LTS0269885
• wikiData: Q104967227