(3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-5-oxo-6a-[(2S,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)propanoic acid

Details

• Internal ID: c9959f28-0aea-4771-8609-0a9e364758a5
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-5-oxo-6a-[(2S,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)propanoic acid
• SMILES (Canonical): C1C(C2C(O1)(C(C(=O)O2)(C(CC(=O)O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]2[C@](O1)([C@](C(=O)O2)([C@H](CC(=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H26O14/c22-6-12-14(27)15(28)16(29)18(33-12)35-21-17(11(24)7-32-21)34-19(30)20(21,31)10(5-13(25)26)8-1-3-9(23)4-2-8/h1-4,10-12,14-18,22-24,27-29,31H,5-7H2,(H,25,26)/t10-,11+,12-,14-,15+,16-,17-,18+,20-,21-/m1/s1
• InChI Key: PQTDFOIAAQSUKY-ZQEZFPCCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₄
• Molecular Weight: 502.40 g/mol
• Exact Mass: 502.13225550 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.49
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5550	55.50%
Caco-2	-	0.9124	91.24%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5603	56.03%
OATP2B1 inhibitior	-	0.8503	85.03%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7271	72.71%
P-glycoprotein inhibitior	-	0.7386	73.86%
P-glycoprotein substrate	-	0.6582	65.82%
CYP3A4 substrate	+	0.6263	62.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.8867	88.67%
CYP2C9 inhibition	-	0.9386	93.86%
CYP2C19 inhibition	-	0.8695	86.95%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.9286	92.86%
CYP2C8 inhibition	-	0.7041	70.41%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5259	52.59%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9379	93.79%
Skin irritation	-	0.8090	80.90%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6400	64.00%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.6881	68.81%
skin sensitisation	-	0.8645	86.45%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7123	71.23%
Acute Oral Toxicity (c)	III	0.5545	55.45%
Estrogen receptor binding	+	0.7577	75.77%
Androgen receptor binding	+	0.6781	67.81%
Thyroid receptor binding	-	0.5718	57.18%
Glucocorticoid receptor binding	+	0.5379	53.79%
Aromatase binding	+	0.6552	65.52%
PPAR gamma	+	0.6042	60.42%
Honey bee toxicity	-	0.7566	75.66%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8050	80.50%
Fish aquatic toxicity	-	0.4106	41.06%

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	99.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.49%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.22%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.97%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.57%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.18%	94.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.01%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	83.89%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.82%	86.92%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.06%	94.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.29%	95.83%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.83%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.72%	99.17%

Plants that contains it

• Viburnum wrightii

Cross-Links

• PubChem: 10391341
• LOTUS: LTS0138294
• wikiData: Q105213438