methyl (1S,4S,5S,8aS,12S,12aS)-4-hydroxy-1,4,5-trimethyl-3,7-dioxo-12-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,8,8a,12,12a-hexahydropyrano[3,4-g][1,5]dioxecine-9-carboxylate

Details

• Internal ID: 4fc7af6a-05e8-4677-aea1-ef1d8444e3cc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1S,4S,5S,8aS,12S,12aS)-4-hydroxy-1,4,5-trimethyl-3,7-dioxo-12-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,8,8a,12,12a-hexahydropyrano[3,4-g][1,5]dioxecine-9-carboxylate
• SMILES (Canonical): CC1C2C(CC(=O)OC(C(C(=O)O1)(C)O)C)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=O)O[C@H]([C@](C(=O)O1)(C)O)C)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)OC
• InChI: InChI=1S/C22H32O14/c1-8-14-10(5-13(24)34-9(2)22(3,30)21(29)33-8)11(18(28)31-4)7-32-19(14)36-20-17(27)16(26)15(25)12(6-23)35-20/h7-10,12,14-17,19-20,23,25-27,30H,5-6H2,1-4H3/t8-,9-,10+,12+,14+,15+,16-,17+,19-,20-,22-/m0/s1
• InChI Key: DXAZCDQDCNQCTJ-UFRLPUKOSA-N
• Popularity: 0 references 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): 208.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.53
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5148	51.48%
Caco-2	-	0.8382	83.82%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6729	67.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7094	70.94%
OATP1B3 inhibitior	+	0.9167	91.67%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8513	85.13%
P-glycoprotein inhibitior	-	0.6027	60.27%
P-glycoprotein substrate	-	0.6073	60.73%
CYP3A4 substrate	+	0.6708	67.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.9134	91.34%
CYP2C9 inhibition	-	0.9062	90.62%
CYP2C19 inhibition	-	0.9174	91.74%
CYP2D6 inhibition	-	0.9406	94.06%
CYP1A2 inhibition	-	0.9094	90.94%
CYP2C8 inhibition	-	0.5947	59.47%
CYP inhibitory promiscuity	-	0.8823	88.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6133	61.33%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9427	94.27%
Skin irritation	-	0.7353	73.53%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4429	44.29%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8616	86.16%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.8239	82.39%
Acute Oral Toxicity (c)	III	0.6156	61.56%
Estrogen receptor binding	+	0.7731	77.31%
Androgen receptor binding	-	0.4872	48.72%
Thyroid receptor binding	-	0.5572	55.72%
Glucocorticoid receptor binding	+	0.5589	55.89%
Aromatase binding	+	0.6030	60.30%
PPAR gamma	+	0.5250	52.50%
Honey bee toxicity	-	0.7948	79.48%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5451	54.51%
Fish aquatic toxicity	-	0.4433	44.33%

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	97.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.34%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.94%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.36%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.09%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	85.54%	92.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.55%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.33%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	83.00%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.56%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.55%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.86%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.73%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.72%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.64%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.26%	95.83%

Plants that contains it

• Gonocaryum calleryanum

Cross-Links

• PubChem: 101921660
• LOTUS: LTS0237033
• wikiData: Q104990899