methyl (1S,4aR,7aR)-4a-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 8700bcdb-9d63-4222-8809-49eb843900bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,7aR)-4a-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1(CC=C2COC3C(C(C(C(O3)CO)O)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@]1(CC=C2CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C23H34O16/c1-34-19(32)9-7-36-20(39-22-18(31)16(29)14(27)11(5-25)38-22)12-8(2-3-23(9,12)33)6-35-21-17(30)15(28)13(26)10(4-24)37-21/h2,7,10-18,20-22,24-31,33H,3-6H2,1H3/t10-,11-,12+,13-,14-,15+,16+,17-,18-,20+,21-,22+,23+/m1/s1
• InChI Key: AKTHOIDCOGDWER-CCAZCNPQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₁₆
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.18468499 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -4.50
• Atomic LogP (AlogP): -5.29
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5830	58.30%
Caco-2	-	0.8886	88.86%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7181	71.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8269	82.69%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7263	72.63%
P-glycoprotein inhibitior	-	0.6234	62.34%
P-glycoprotein substrate	-	0.7146	71.46%
CYP3A4 substrate	+	0.6478	64.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9781	97.81%
CYP2C9 inhibition	-	0.9398	93.98%
CYP2C19 inhibition	-	0.8545	85.45%
CYP2D6 inhibition	-	0.9105	91.05%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	-	0.5665	56.65%
CYP inhibitory promiscuity	-	0.9294	92.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6510	65.10%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9330	93.30%
Skin irritation	-	0.7602	76.02%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7475	74.75%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7199	71.99%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5715	57.15%
Acute Oral Toxicity (c)	III	0.3747	37.47%
Estrogen receptor binding	+	0.6496	64.96%
Androgen receptor binding	+	0.6277	62.77%
Thyroid receptor binding	-	0.5213	52.13%
Glucocorticoid receptor binding	+	0.5427	54.27%
Aromatase binding	+	0.7071	70.71%
PPAR gamma	+	0.5479	54.79%
Honey bee toxicity	-	0.7906	79.06%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.3706	37.06%

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	98.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.10%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.42%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.98%	96.61%
CHEMBL2581	P07339	Cathepsin D	87.21%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.50%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.39%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.91%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.18%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.55%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	82.32%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.81%	99.17%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.48%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.39%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.22%	94.00%

Plants that contains it

• Cryptomeria japonica
• Cycas beddomei
• Cycas revoluta
• Libocedrus bidwillii
• Selaginella uncinata

Cross-Links

• PubChem: 10325616
• LOTUS: LTS0189695
• wikiData: Q105135556