methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: bcd232e4-9dd2-4043-9bd4-ed5ec222fdfa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O
• InChI: InChI=1S/C22H32O14/c1-31-18(29)11-5-32-19(13-9(4-23)2-3-10(11)13)36-20-16(27)15(26)14(25)12(35-20)6-33-21-17(28)22(30,7-24)8-34-21/h2,5,10,12-17,19-21,23-28,30H,3-4,6-8H2,1H3/t10-,12-,13-,14-,15+,16-,17+,19+,20+,21-,22-/m1/s1
• InChI Key: OOUBSPPBTVIADD-IDPBDCHGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₁₄
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.17920569 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -3.76
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6500	65.00%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7412	74.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8436	84.36%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7929	79.29%
P-glycoprotein inhibitior	-	0.6769	67.69%
P-glycoprotein substrate	-	0.5423	54.23%
CYP3A4 substrate	+	0.6832	68.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9720	97.20%
CYP2C9 inhibition	-	0.9350	93.50%
CYP2C19 inhibition	-	0.8594	85.94%
CYP2D6 inhibition	-	0.9076	90.76%
CYP1A2 inhibition	-	0.9207	92.07%
CYP2C8 inhibition	+	0.5549	55.49%
CYP inhibitory promiscuity	-	0.8997	89.97%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5997	59.97%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9408	94.08%
Skin irritation	-	0.7552	75.52%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7420	74.20%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8619	86.19%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.8229	82.29%
Acute Oral Toxicity (c)	III	0.3751	37.51%
Estrogen receptor binding	+	0.7091	70.91%
Androgen receptor binding	+	0.5728	57.28%
Thyroid receptor binding	-	0.5717	57.17%
Glucocorticoid receptor binding	-	0.4727	47.27%
Aromatase binding	+	0.6478	64.78%
PPAR gamma	+	0.5361	53.61%
Honey bee toxicity	-	0.7980	79.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.6792	67.92%

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	98.25%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.07%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.23%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.44%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	85.45%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.79%	94.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.64%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.18%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.05%	96.90%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.03%	96.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.70%	95.83%
CHEMBL5028	O14672	ADAM10	83.41%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	82.84%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.55%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.51%	99.23%
CHEMBL4208	P20618	Proteasome component C5	82.12%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.91%	94.45%
CHEMBL2581	P07339	Cathepsin D	81.74%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.14%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.13%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.11%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.89%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	80.86%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.76%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.69%	97.21%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 71552450
• NPASS: NPC86095
• LOTUS: LTS0136539
• wikiData: Q105195596