methyl (1R,4aS,8S,8aS)-1-methyl-3-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylate

Details

• Internal ID: bf2d8e22-a1da-433b-ad83-5e925703c43b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1R,4aS,8S,8aS)-1-methyl-3-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylate
• SMILES (Canonical): CC1C2C(CC(=O)O1)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)O1)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/C17H24O11/c1-6-11-7(3-10(19)26-6)8(15(23)24-2)5-25-16(11)28-17-14(22)13(21)12(20)9(4-18)27-17/h5-7,9,11-14,16-18,20-22H,3-4H2,1-2H3/t6-,7-,9-,11-,12-,13+,14-,16+,17+/m1/s1
• InChI Key: QZCJFXSHMSZCLH-XICRDADBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 11
• 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	-	0.5842	58.42%
Caco-2	-	0.8453	84.53%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6715	67.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3374	33.74%
OATP1B3 inhibitior	+	0.9560	95.60%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8365	83.65%
P-glycoprotein inhibitior	-	0.8371	83.71%
P-glycoprotein substrate	-	0.7427	74.27%
CYP3A4 substrate	+	0.5951	59.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8889	88.89%
CYP3A4 inhibition	-	0.8840	88.40%
CYP2C9 inhibition	-	0.8855	88.55%
CYP2C19 inhibition	-	0.9133	91.33%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.9162	91.62%
CYP2C8 inhibition	-	0.6879	68.79%
CYP inhibitory promiscuity	-	0.8450	84.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6718	67.18%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9506	95.06%
Skin irritation	-	0.7837	78.37%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5321	53.21%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.6696	66.96%
skin sensitisation	-	0.8807	88.07%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6582	65.82%
Acute Oral Toxicity (c)	III	0.5768	57.68%
Estrogen receptor binding	+	0.5417	54.17%
Androgen receptor binding	-	0.5520	55.20%
Thyroid receptor binding	-	0.6298	62.98%
Glucocorticoid receptor binding	-	0.5948	59.48%
Aromatase binding	-	0.5831	58.31%
PPAR gamma	-	0.5857	58.57%
Honey bee toxicity	-	0.8515	85.15%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4547	45.47%

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	96.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.56%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.52%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	85.65%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	84.82%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.39%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.15%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.42%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.32%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.26%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.21%	90.00%

Plants that contains it

• Citronella gongonha
• Fraxinus griffithii
• Gentiana pyrenaica
• Jasminum polyanthum
• Lamium amplexicaule
• Ligusticum lucidum
• Ligustrum japonicum
• Ligustrum lucidum
• Loasa illapelina
• Picconia excelsa
• Syringa vulgaris

Cross-Links

• PubChem: 12304886
• LOTUS: LTS0091215
• wikiData: Q104392953