[(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[4-hydroxy-2-[[(1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl]oxymethyl]phenoxy]-6-(hydroxymethyl)oxan-4-yl] benzoate

Details

• Internal ID: 40b74e4d-ca7d-40f6-9eb8-c75f4a7cc5c5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[4-hydroxy-2-[[(1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl]oxymethyl]phenoxy]-6-(hydroxymethyl)oxan-4-yl] benzoate
• SMILES (Canonical): C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)O)OC(=O)C4=CC=CC=C4)O)O
• SMILES (Isomeric): C1CC(=O)[C@](C=C1)(C(=O)OCC2=C(C=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)OC(=O)C4=CC=CC=C4)O)O
• InChI: InChI=1S/C27H28O12/c28-13-19-21(31)23(39-24(33)15-6-2-1-3-7-15)22(32)25(38-19)37-18-10-9-17(29)12-16(18)14-36-26(34)27(35)11-5-4-8-20(27)30/h1-3,5-7,9-12,19,21-23,25,28-29,31-32,35H,4,8,13-14H2/t19-,21-,22-,23+,25-,27-/m1/s1
• InChI Key: LZMZVGLTYMYFFB-XEQWYTIESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₂
• Molecular Weight: 544.50 g/mol
• Exact Mass: 544.15807632 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5983	59.83%
Caco-2	-	0.9062	90.62%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7230	72.30%
OATP2B1 inhibitior	-	0.8426	84.26%
OATP1B1 inhibitior	+	0.8601	86.01%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4835	48.35%
P-glycoprotein inhibitior	+	0.6543	65.43%
P-glycoprotein substrate	-	0.6346	63.46%
CYP3A4 substrate	+	0.6711	67.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.8481	84.81%
CYP2C9 inhibition	-	0.5188	51.88%
CYP2C19 inhibition	-	0.7374	73.74%
CYP2D6 inhibition	-	0.9213	92.13%
CYP1A2 inhibition	-	0.8873	88.73%
CYP2C8 inhibition	+	0.7495	74.95%
CYP inhibitory promiscuity	-	0.7184	71.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9428	94.28%
Carcinogenicity (trinary)	Non-required	0.6538	65.38%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8970	89.70%
Skin irritation	-	0.8400	84.00%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5217	52.17%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.5677	56.77%
skin sensitisation	-	0.8458	84.58%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6318	63.18%
Acute Oral Toxicity (c)	III	0.6578	65.78%
Estrogen receptor binding	+	0.7176	71.76%
Androgen receptor binding	+	0.7208	72.08%
Thyroid receptor binding	-	0.5743	57.43%
Glucocorticoid receptor binding	+	0.5749	57.49%
Aromatase binding	-	0.5062	50.62%
PPAR gamma	+	0.6309	63.09%
Honey bee toxicity	-	0.7698	76.98%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.8494	84.94%

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	99.04%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.74%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.49%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.49%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.97%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.19%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.21%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.43%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.41%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.33%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.31%	94.00%
CHEMBL3891	P07384	Calpain 1	85.17%	93.04%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.82%	83.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.30%	94.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.83%	92.62%
CHEMBL4208	P20618	Proteasome component C5	82.93%	90.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.06%	89.67%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.67%	95.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.97%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	80.17%	95.93%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.06%	97.33%

Plants that contains it

• Itoa orientalis

Cross-Links

• PubChem: 162982613
• LOTUS: LTS0184672
• wikiData: Q105160017