2-[(2S,3S,4S)-3-[(1S)-1-acetyloxyethyl]-5-methoxycarbonyl-2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid

Details

• Internal ID: 29227f98-8c55-47b1-996e-0e564ff721bb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 2-[(2S,3S,4S)-3-[(1S)-1-acetyloxyethyl]-5-methoxycarbonyl-2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid
• SMILES (Canonical): CC(C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]([C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@H]([C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)O)OC(=O)C
• InChI: InChI=1S/C19H28O13/c1-7(30-8(2)21)13-9(4-12(22)23)10(17(27)28-3)6-29-18(13)32-19-16(26)15(25)14(24)11(5-20)31-19/h6-7,9,11,13-16,18-20,24-26H,4-5H2,1-3H3,(H,22,23)/t7-,9+,11+,13+,14+,15+,16-,18-,19-/m0/s1
• InChI Key: OPKOYMHTMXJHRG-YCXKLPKRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₁₃
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.15299094 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.13
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7692	76.92%
Caco-2	-	0.8406	84.06%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6696	66.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7636	76.36%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7982	79.82%
P-glycoprotein inhibitior	-	0.7481	74.81%
P-glycoprotein substrate	-	0.6917	69.17%
CYP3A4 substrate	+	0.6023	60.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.8777	87.77%
CYP2C9 inhibition	-	0.8997	89.97%
CYP2C19 inhibition	-	0.9151	91.51%
CYP2D6 inhibition	-	0.9143	91.43%
CYP1A2 inhibition	-	0.9396	93.96%
CYP2C8 inhibition	-	0.6887	68.87%
CYP inhibitory promiscuity	-	0.9362	93.62%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6852	68.52%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9417	94.17%
Skin irritation	-	0.7956	79.56%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5153	51.53%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	-	0.7449	74.49%
skin sensitisation	-	0.8761	87.61%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4858	48.58%
Acute Oral Toxicity (c)	III	0.6528	65.28%
Estrogen receptor binding	+	0.6797	67.97%
Androgen receptor binding	-	0.5449	54.49%
Thyroid receptor binding	-	0.5567	55.67%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5453	54.53%
PPAR gamma	-	0.5397	53.97%
Honey bee toxicity	-	0.8232	82.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.5867	58.67%

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	97.24%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.90%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.64%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.51%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.33%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.69%	96.00%
CHEMBL5028	O14672	ADAM10	83.43%	97.50%
CHEMBL3776	Q14790	Caspase-8	80.64%	97.06%

Plants that contains it

• Calycophyllum spruceanum
• Chione venosa
• Nauclea diderrichii

Cross-Links

• PubChem: 162949268
• LOTUS: LTS0092981
• wikiData: Q105196414