Prunetin 4'-O-glucoside

Details

• Internal ID: cf9f1c7a-67ba-4f8c-890e-a1edfd659e9d
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-7-methoxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-12-6-14(24)17-15(7-12)30-9-13(18(17)25)10-2-4-11(5-3-10)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1
• InChI Key: OFUWGCQDMVDLIR-RECXWPGBSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• Prunetin 4'-O-glucoside
• Trifoside
• CHEBI:78742
• 154-36-9
• prunitrin
• 5-hydroxy-7-methoxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• MLS001165137
• CHEMBL1568702
• DTXSID201318705
• HMS2883M16
• HY-N7645
• AKOS002181851
• 5-hydroxy-7-methoxy-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4H-chromen-4-one
• MS-28046
• SMR000540442
• CS-0134949
• VU0510097-1
• Q27147936
• 4'-(beta-D-glucosyloxy)- 5-hydroxy-7-methoxyisoflavone
• F3139-0724
• 5,4'-dihydroxy-7-methoxyisoflavone 4'-O-beta-D-glucoside
• 4-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)phenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8486	84.86%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5639	56.39%
OATP1B1 inhibitior	+	0.9458	94.58%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7491	74.91%
P-glycoprotein inhibitior	-	0.5571	55.71%
P-glycoprotein substrate	-	0.8735	87.35%
CYP3A4 substrate	+	0.6130	61.30%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6060	60.60%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5933	59.33%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6434	64.34%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7190	71.90%
Androgen receptor binding	+	0.7181	71.81%
Thyroid receptor binding	+	0.5795	57.95%
Glucocorticoid receptor binding	+	0.5866	58.66%
Aromatase binding	+	0.5446	54.46%
PPAR gamma	+	0.8040	80.40%
Honey bee toxicity	-	0.8161	81.61%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7079	70.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	1584.9 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3981.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.51%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.72%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.27%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.42%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.73%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.72%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.47%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.97%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.75%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.13%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.20%	96.21%
CHEMBL4208	P20618	Proteasome component C5	86.52%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	85.65%	93.31%
CHEMBL226	P30542	Adenosine A1 receptor	84.93%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.75%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.35%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	81.21%	94.73%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.68%	97.28%

Plants that contains it

• Achillea lycaonica
• Albizia gummifera
• Citrus maxima
• Dalbergia sissoo
• Ducrosia ismaelis
• Styphnolobium japonicum
• Trifolium pratense

Cross-Links

• PubChem: 16398538
• NPASS: NPC73511
• ChEMBL: CHEMBL1568702
• LOTUS: LTS0150791
• wikiData: Q27147936