(2S,3R,4S,5S,6R)-6-((Cinnamoyloxy)methyl)-4,5-dihydroxy-2-(4-(3-oxobutyl)phenoxy)tetrahydro-2H-pyran-3-yl 3,4,5-trihydroxybenzoate

Details

• Internal ID: e8d12857-7dea-4156-966e-25f16562ef62
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[4-(3-oxobutyl)phenoxy]-6-[[(E)-3-phenylprop-2-enoyl]oxymethyl]oxan-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC(=O)CCC1=CC=C(C=C1)OC2C(C(C(C(O2)COC(=O)C=CC3=CC=CC=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• SMILES (Isomeric): CC(=O)CCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC=CC=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• InChI: InChI=1S/C32H32O12/c1-18(33)7-8-20-9-12-22(13-10-20)42-32-30(44-31(40)21-15-23(34)27(37)24(35)16-21)29(39)28(38)25(43-32)17-41-26(36)14-11-19-5-3-2-4-6-19/h2-6,9-16,25,28-30,32,34-35,37-39H,7-8,17H2,1H3/b14-11+/t25-,28-,29+,30-,32-/m1/s1
• InChI Key: AHLBWJHZDLMJOJ-SIHJTGPPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₂O₁₂
• Molecular Weight: 608.60 g/mol
• Exact Mass: 608.18937645 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• 105274-15-5
• (2S,3R,4S,5S,6R)-6-((Cinnamoyloxy)methyl)-4,5-dihydroxy-2-(4-(3-oxobutyl)phenoxy)tetrahydro-2H-pyran-3-yl 3,4,5-trihydroxybenzoate
• [(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[4-(3-oxobutyl)phenoxy]-6-[[(E)-3-phenylprop-2-enoyl]oxymethyl]oxan-3-yl] 3,4,5-trihydroxybenzoate
• 2-Butanone, 4-[4-[[6-O-[(2E)-1-oxo-3-phenyl-2-propen-1-yl]-2-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]oxy]phenyl]-
• DTXSID301105705
• AKOS037515322
• 4-(3-Oxobutyl)phenyl 2-O-galloyl-6-O-cinnamoyl-beta-D-glucopyranoside
• 4-[4-[[6-O-[(2E)-1-Oxo-3-phenyl-2-propen-1-yl]-2-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]oxy]phenyl]-2-butanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5365	53.65%
Caco-2	-	0.8802	88.02%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7992	79.92%
OATP2B1 inhibitior	-	0.7075	70.75%
OATP1B1 inhibitior	+	0.7282	72.82%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7873	78.73%
P-glycoprotein inhibitior	+	0.7201	72.01%
P-glycoprotein substrate	-	0.5943	59.43%
CYP3A4 substrate	+	0.6643	66.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8740	87.40%
CYP3A4 inhibition	-	0.7481	74.81%
CYP2C9 inhibition	-	0.6401	64.01%
CYP2C19 inhibition	-	0.7353	73.53%
CYP2D6 inhibition	-	0.8854	88.54%
CYP1A2 inhibition	-	0.5927	59.27%
CYP2C8 inhibition	+	0.8549	85.49%
CYP inhibitory promiscuity	-	0.7851	78.51%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7370	73.70%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.7855	78.55%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6900	69.00%
Micronuclear	-	0.7326	73.26%
Hepatotoxicity	-	0.7738	77.38%
skin sensitisation	-	0.8424	84.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9899	98.99%
Acute Oral Toxicity (c)	III	0.7400	74.00%
Estrogen receptor binding	+	0.7889	78.89%
Androgen receptor binding	+	0.7331	73.31%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6275	62.75%
Aromatase binding	-	0.5204	52.04%
PPAR gamma	+	0.6718	67.18%
Honey bee toxicity	-	0.7355	73.55%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9859	98.59%

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	99.68%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	99.04%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	98.62%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.96%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.63%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.38%	96.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	93.18%	83.00%
CHEMBL3401	O75469	Pregnane X receptor	93.17%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.64%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	91.37%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.69%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.72%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.33%	97.21%
CHEMBL3194	P02766	Transthyretin	88.48%	90.71%
CHEMBL4208	P20618	Proteasome component C5	88.04%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.92%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.73%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.39%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.87%	97.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.81%	95.64%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.07%	95.17%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.63%	94.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.44%	89.34%

Plants that contains it

• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 10258149
• NPASS: NPC31013