[2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyphenyl]methyl (1R,2R,6R)-1,2,6-trihydroxy-5-oxocyclohex-3-ene-1-carboxylate

Details

• Internal ID: 85f64d40-312a-4a4e-a35b-2132f283d793
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyphenyl]methyl (1R,2R,6R)-1,2,6-trihydroxy-5-oxocyclohex-3-ene-1-carboxylate
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)OC2C(C(C(OC2OC3=C(C=C(C=C3)O)COC(=O)C4(C(C=CC(=O)C4O)O)O)CO)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C(C=C(C=C3)O)COC(=O)[C@]4([C@@H](C=CC(=O)[C@@H]4O)O)O)CO)O)O
• InChI: InChI=1S/C27H28O14/c28-11-18-20(32)21(33)22(41-24(35)13-4-2-1-3-5-13)25(40-18)39-17-8-6-15(29)10-14(17)12-38-26(36)27(37)19(31)9-7-16(30)23(27)34/h1-10,18-23,25,28-29,31-34,37H,11-12H2/t18-,19-,20-,21+,22-,23+,25-,27-/m1/s1
• InChI Key: DLBOMVFEFWKKHS-MUZBHQQFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₄
• Molecular Weight: 576.50 g/mol
• Exact Mass: 576.14790556 g/mol
• Topological Polar Surface Area (TPSA): 230.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.93
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7343	73.43%
Caco-2	-	0.9155	91.55%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6258	62.58%
OATP2B1 inhibitior	-	0.8412	84.12%
OATP1B1 inhibitior	+	0.8179	81.79%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8015	80.15%
P-glycoprotein inhibitior	+	0.6144	61.44%
P-glycoprotein substrate	-	0.6026	60.26%
CYP3A4 substrate	+	0.6771	67.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8779	87.79%
CYP3A4 inhibition	-	0.8524	85.24%
CYP2C9 inhibition	-	0.8099	80.99%
CYP2C19 inhibition	-	0.8260	82.60%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.9131	91.31%
CYP2C8 inhibition	+	0.7173	71.73%
CYP inhibitory promiscuity	-	0.8019	80.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6658	66.58%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9184	91.84%
Skin irritation	-	0.8533	85.33%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3824	38.24%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7987	79.87%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5905	59.05%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	+	0.7461	74.61%
Androgen receptor binding	+	0.6902	69.02%
Thyroid receptor binding	+	0.5164	51.64%
Glucocorticoid receptor binding	+	0.5526	55.26%
Aromatase binding	-	0.4881	48.81%
PPAR gamma	+	0.6336	63.36%
Honey bee toxicity	-	0.7319	73.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6149	61.49%
Fish aquatic toxicity	+	0.9179	91.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.57%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.37%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.56%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.80%	94.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.43%	86.33%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	89.64%	97.53%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.47%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.05%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.75%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.38%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.22%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.45%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.71%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.41%	95.89%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.32%	94.08%
CHEMBL3891	P07384	Calpain 1	84.15%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.53%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.53%	83.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.36%	89.67%

Plants that contains it

• Alstonia lanceolifera
• Flacourtia indica

Cross-Links

• PubChem: 71575417
• NPASS: NPC57072
• ChEMBL: CHEMBL2316620
• LOTUS: LTS0020728
• wikiData: Q105028090