(3S,4S,4aS)-4-acetyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

Details

• Internal ID: 4ffaf7ae-e23f-4a7f-a734-b2e020f37766
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4S,4aS)-4-acetyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• SMILES (Canonical): CC(=O)C1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(=O)[C@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H22O10/c1-6(18)10-7-2-3-23-14(22)8(7)5-24-15(10)26-16-13(21)12(20)11(19)9(4-17)25-16/h5,7,9-13,15-17,19-21H,2-4H2,1H3/t7-,9-,10+,11-,12+,13-,15+,16+/m1/s1
• InChI Key: ONWIFIWSHIQJQH-XDQMPBQCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34 g/mol
• Exact Mass: 374.12129689 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.19
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6519	65.19%
Caco-2	-	0.8963	89.63%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8372	83.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7820	78.20%
P-glycoprotein inhibitior	-	0.8792	87.92%
P-glycoprotein substrate	-	0.8688	86.88%
CYP3A4 substrate	+	0.6030	60.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.9564	95.64%
CYP2C9 inhibition	-	0.8616	86.16%
CYP2C19 inhibition	-	0.8874	88.74%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.8356	83.56%
CYP2C8 inhibition	-	0.7693	76.93%
CYP inhibitory promiscuity	-	0.8792	87.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5866	58.66%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7494	74.94%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5810	58.10%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8822	88.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5258	52.58%
Acute Oral Toxicity (c)	III	0.5720	57.20%
Estrogen receptor binding	+	0.5882	58.82%
Androgen receptor binding	+	0.5787	57.87%
Thyroid receptor binding	-	0.5807	58.07%
Glucocorticoid receptor binding	-	0.5972	59.72%
Aromatase binding	-	0.6688	66.88%
PPAR gamma	-	0.4923	49.23%
Honey bee toxicity	-	0.8747	87.47%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.4584	45.84%

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	97.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.17%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.96%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.14%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.76%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.55%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.81%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	80.28%	94.73%

Plants that contains it

• Lamium album

Cross-Links

• PubChem: 162921845
• LOTUS: LTS0199266
• wikiData: Q105195183