Methyl 4a,7-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: c9afc6cb-3a06-4f4f-a87a-64c67ef13dd9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 4a,7-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(C(CC2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O)O
• SMILES (Isomeric): CC1(C(CC2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O)O
• InChI: InChI=1S/C26H32O14/c1-25(34)16(39-17(29)8-5-12-3-6-13(28)7-4-12)9-26(35)14(22(33)36-2)11-37-24(21(25)26)40-23-20(32)19(31)18(30)15(10-27)38-23/h3-8,11,15-16,18-21,23-24,27-28,30-32,34-35H,9-10H2,1-2H3
• InChI Key: NQXDDVZOWBZZHN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₄
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.17920569 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 14
• 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	+	0.8160	81.60%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5543	55.43%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8050	80.50%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6161	61.61%
P-glycoprotein inhibitior	-	0.5507	55.07%
P-glycoprotein substrate	-	0.5156	51.56%
CYP3A4 substrate	+	0.6998	69.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8591	85.91%
CYP2C9 inhibition	-	0.8666	86.66%
CYP2C19 inhibition	-	0.8875	88.75%
CYP2D6 inhibition	-	0.8996	89.96%
CYP1A2 inhibition	-	0.8225	82.25%
CYP2C8 inhibition	+	0.7463	74.63%
CYP inhibitory promiscuity	-	0.8524	85.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6431	64.31%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9335	93.35%
Skin irritation	-	0.7076	70.76%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3941	39.41%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.8120	81.20%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7452	74.52%
Acute Oral Toxicity (c)	I	0.4052	40.52%
Estrogen receptor binding	+	0.8124	81.24%
Androgen receptor binding	+	0.6724	67.24%
Thyroid receptor binding	+	0.5618	56.18%
Glucocorticoid receptor binding	+	0.6713	67.13%
Aromatase binding	+	0.6016	60.16%
PPAR gamma	+	0.7008	70.08%
Honey bee toxicity	-	0.7365	73.65%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8708	87.08%

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	99.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.71%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.05%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.73%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.02%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.89%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.69%	97.28%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.45%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.18%	89.67%
CHEMBL2581	P07339	Cathepsin D	85.50%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.04%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.60%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.39%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.59%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.84%	94.33%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.77%	88.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.68%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.32%	90.00%

Plants that contains it

• Bouchea pseudogervao
• Duranta erecta

Cross-Links

• PubChem: 74124637
• LOTUS: LTS0024039
• wikiData: Q105184170