[(1R,4S,5R,6S,7R,8S,9S)-4,5-dihydroxy-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undecan-6-yl] 4-hydroxybenzoate

Details

• Internal ID: 2f66b8d4-4a42-49ae-8561-1affd58f1d6d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(1R,4S,5R,6S,7R,8S,9S)-4,5-dihydroxy-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undecan-6-yl] 4-hydroxybenzoate
• SMILES (Canonical): C1C2C3C(OC1OCC3(C(C2OC(=O)C4=CC=C(C=C4)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1[C@@H]2[C@@H]3[C@@H](O[C@H]1OC[C@@]3([C@@H]([C@H]2OC(=O)C4=CC=C(C=C4)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C22H28O13/c23-6-11-14(25)15(26)16(27)21(32-11)35-20-13-10-5-12(33-20)31-7-22(13,30)18(28)17(10)34-19(29)8-1-3-9(24)4-2-8/h1-4,10-18,20-21,23-28,30H,5-7H2/t10-,11-,12-,13-,14-,15+,16-,17+,18-,20+,21+,22-/m1/s1
• InChI Key: VATOVCBALSEIIZ-LGBACTKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₃
• Molecular Weight: 500.40 g/mol
• Exact Mass: 500.15299094 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.83
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4857	48.57%
Caco-2	-	0.9024	90.24%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5810	58.10%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7859	78.59%
P-glycoprotein inhibitior	-	0.7480	74.80%
P-glycoprotein substrate	-	0.6319	63.19%
CYP3A4 substrate	+	0.6661	66.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8447	84.47%
CYP3A4 inhibition	-	0.8685	86.85%
CYP2C9 inhibition	-	0.9495	94.95%
CYP2C19 inhibition	-	0.7710	77.10%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.9098	90.98%
CYP2C8 inhibition	+	0.7422	74.22%
CYP inhibitory promiscuity	-	0.9432	94.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6076	60.76%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.7961	79.61%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6086	60.86%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8742	87.42%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5940	59.40%
Acute Oral Toxicity (c)	III	0.4292	42.92%
Estrogen receptor binding	+	0.7493	74.93%
Androgen receptor binding	-	0.4822	48.22%
Thyroid receptor binding	+	0.5861	58.61%
Glucocorticoid receptor binding	-	0.5072	50.72%
Aromatase binding	+	0.7873	78.73%
PPAR gamma	+	0.7320	73.20%
Honey bee toxicity	-	0.7142	71.42%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7879	78.79%

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	97.80%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.80%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.83%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	90.79%	94.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.77%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.27%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.14%	98.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.72%	85.00%
CHEMBL4208	P20618	Proteasome component C5	86.21%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.31%	99.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.70%	94.23%
CHEMBL5255	O00206	Toll-like receptor 4	84.29%	92.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.72%	97.79%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.32%	89.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.94%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.65%	91.49%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.61%	94.00%

Plants that contains it

• Catalpa bignonioides

Cross-Links

• PubChem: 101619543
• LOTUS: LTS0216488
• wikiData: Q105282979