ethyl (1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 90473692-87e2-44a1-8a71-366878a1af58
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: ethyl (1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CCOC(=O)C1=COC(C2C1C(C=C2COC(=O)C)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CCOC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@H](C=C2COC(=O)C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C20H28O12/c1-3-28-18(27)10-7-30-19(13-9(6-29-8(2)22)4-11(23)14(10)13)32-20-17(26)16(25)15(24)12(5-21)31-20/h4,7,11-17,19-21,23-26H,3,5-6H2,1-2H3/t11-,12+,13+,14-,15+,16-,17+,19-,20-/m0/s1
• InChI Key: CWBXOWNEYBLJQQ-JQGWABBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₁₂
• Molecular Weight: 460.40 g/mol
• Exact Mass: 460.15807632 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.30
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6762	67.62%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7052	70.52%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.7810	78.10%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7565	75.65%
P-glycoprotein inhibitior	-	0.7725	77.25%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.6170	61.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8891	88.91%
CYP3A4 inhibition	-	0.9046	90.46%
CYP2C9 inhibition	-	0.8768	87.68%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.9219	92.19%
CYP1A2 inhibition	-	0.8725	87.25%
CYP2C8 inhibition	-	0.6132	61.32%
CYP inhibitory promiscuity	-	0.7671	76.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7308	73.08%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7488	74.88%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4403	44.03%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8833	88.33%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.8210	82.10%
Acute Oral Toxicity (c)	III	0.5363	53.63%
Estrogen receptor binding	+	0.7061	70.61%
Androgen receptor binding	+	0.5546	55.46%
Thyroid receptor binding	-	0.6345	63.45%
Glucocorticoid receptor binding	-	0.5155	51.55%
Aromatase binding	+	0.5189	51.89%
PPAR gamma	-	0.5327	53.27%
Honey bee toxicity	-	0.7757	77.57%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7605	76.05%
Fish aquatic toxicity	+	0.8494	84.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.85%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.41%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.41%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.46%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	82.62%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.51%	86.33%

Plants that contains it

• Exallage chrysotricha

Cross-Links

• PubChem: 21580986
• LOTUS: LTS0108083
• wikiData: Q104971149