methyl (1S,3'R,4'R,4aS,7S,7aS)-3'-hydroxy-4'-[(4-hydroxyphenyl)methyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxolane]-4-carboxylate

Details

• Internal ID: 5fcd888c-8c44-49d7-957a-950647afc437
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,3'R,4'R,4aS,7S,7aS)-3'-hydroxy-4'-[(4-hydroxyphenyl)methyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxolane]-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C=CC23C(C(C(=O)O3)CC4=CC=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C=C[C@@]23[C@@H]([C@H](C(=O)O3)CC4=CC=C(C=C4)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C26H30O13/c1-35-22(33)15-10-36-24(38-25-20(31)19(30)18(29)16(9-27)37-25)17-13(15)6-7-26(17)21(32)14(23(34)39-26)8-11-2-4-12(28)5-3-11/h2-7,10,13-14,16-21,24-25,27-32H,8-9H2,1H3/t13-,14-,16-,17-,18-,19+,20-,21-,24+,25+,26+/m1/s1
• InChI Key: LDPOHYHZJSBJQD-YONCCBDYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₃
• Molecular Weight: 550.50 g/mol
• Exact Mass: 550.16864101 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.76
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7577	75.77%
Caco-2	-	0.9187	91.87%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7037	70.37%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.7453	74.53%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5095	50.95%
P-glycoprotein inhibitior	-	0.5493	54.93%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6967	69.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8661	86.61%
CYP3A4 inhibition	-	0.8655	86.55%
CYP2C9 inhibition	-	0.7707	77.07%
CYP2C19 inhibition	-	0.7641	76.41%
CYP2D6 inhibition	-	0.9005	90.05%
CYP1A2 inhibition	-	0.8652	86.52%
CYP2C8 inhibition	+	0.7289	72.89%
CYP inhibitory promiscuity	-	0.6292	62.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9349	93.49%
Skin irritation	-	0.7627	76.27%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6735	67.35%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6707	67.07%
skin sensitisation	-	0.8145	81.45%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8126	81.26%
Acute Oral Toxicity (c)	III	0.5234	52.34%
Estrogen receptor binding	+	0.8052	80.52%
Androgen receptor binding	+	0.6800	68.00%
Thyroid receptor binding	+	0.5180	51.80%
Glucocorticoid receptor binding	+	0.6696	66.96%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6817	68.17%
Honey bee toxicity	-	0.7132	71.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8306	83.06%

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	98.72%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.51%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	93.59%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.47%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.51%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.96%	89.67%
CHEMBL4208	P20618	Proteasome component C5	88.63%	90.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.79%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.68%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.10%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.74%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.35%	89.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.93%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.14%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.91%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.57%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.22%	95.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.62%	94.00%

Plants that contains it

• Dunnia sinensis

Cross-Links

• PubChem: 102237316
• LOTUS: LTS0160108
• wikiData: Q105150318