methyl (3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-5-oxo-6a-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a-dihydro-2H-furo[3,2-b]furan-6-yl]-3-(4-hydroxyphenyl)propanoate

Details

• Internal ID: 63d30e57-3a4e-473d-ae52-cf0e4c2516c5
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: methyl (3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-5-oxo-6a-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a-dihydro-2H-furo[3,2-b]furan-6-yl]-3-(4-hydroxyphenyl)propanoate
• SMILES (Canonical): COC(=O)CC(C1=CC=C(C=C1)O)C2(C(=O)OC3C2(OCC3O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC(=O)C[C@H](C1=CC=C(C=C1)O)[C@]2(C(=O)O[C@H]3[C@@]2(OC[C@@H]3O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H28O14/c1-32-14(26)6-11(9-2-4-10(24)5-3-9)21(31)20(30)35-18-12(25)8-33-22(18,21)36-19-17(29)16(28)15(27)13(7-23)34-19/h2-5,11-13,15-19,23-25,27-29,31H,6-8H2,1H3/t11-,12+,13-,15-,16+,17-,18-,19-,21-,22-/m1/s1
• InChI Key: IWKUCGXPQSYUMV-WYFAWWTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₄
• Molecular Weight: 516.40 g/mol
• Exact Mass: 516.14790556 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.40
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6182	61.82%
Caco-2	-	0.8859	88.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5413	54.13%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8602	86.02%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5652	56.52%
P-glycoprotein inhibitior	-	0.7018	70.18%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6576	65.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8665	86.65%
CYP3A4 inhibition	-	0.9375	93.75%
CYP2C9 inhibition	-	0.9312	93.12%
CYP2C19 inhibition	-	0.8968	89.68%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.9129	91.29%
CYP2C8 inhibition	-	0.6638	66.38%
CYP inhibitory promiscuity	-	0.9192	91.92%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5397	53.97%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.7901	79.01%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6651	66.51%
Micronuclear	-	0.5967	59.67%
Hepatotoxicity	-	0.6954	69.54%
skin sensitisation	-	0.8739	87.39%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4840	48.40%
Acute Oral Toxicity (c)	III	0.6618	66.18%
Estrogen receptor binding	+	0.7591	75.91%
Androgen receptor binding	+	0.6855	68.55%
Thyroid receptor binding	-	0.5581	55.81%
Glucocorticoid receptor binding	+	0.6098	60.98%
Aromatase binding	+	0.6638	66.38%
PPAR gamma	+	0.6091	60.91%
Honey bee toxicity	-	0.7745	77.45%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.3994	39.94%

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	99.26%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.21%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.99%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.34%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.29%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.09%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.05%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.69%	93.10%
CHEMBL340	P08684	Cytochrome P450 3A4	86.28%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.99%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.85%	95.56%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.32%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.07%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	82.87%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.69%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.99%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.92%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.33%	94.80%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.00%	85.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.17%	96.90%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.06%	94.00%

Plants that contains it

• Viburnum wrightii

Cross-Links

• PubChem: 162901295
• LOTUS: LTS0252462
• wikiData: Q105121704