Quercetin pentaacetate

Details

• Internal ID: 58508f2b-d230-4a9c-b7de-86ccb22b3dc3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: [2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate
• SMILES (Canonical): CC(=O)OC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H20O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10H,1-5H3
• InChI Key: JQUHMSXLZZWRHU-UHFFFAOYSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₀O₁₂
• Molecular Weight: 512.40 g/mol
• Exact Mass: 512.09547607 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 1064-06-8
• 3,3',4',5,7-Pentaacetoxyflavone
• G0B9KJ0VKI
• 4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-(3,4-bis(acetyloxy)phenyl)-
• FLAVONE, 3,3',4',5,7-PENTAHYDROXY-, PENTAACETATE
• DTXSID30147593
• RefChem:930461
• DTXCID9070084
• Pentaacetylquercetin
• Quercetin acetate
• QUERCETINPENTAACETATE
• NSC-115919
• [2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate
• 3,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-5-yl acetate
• C25H20O12
• NSC 115919
• BRN 0380215
• 3,3',4',5,7-Pentahydroxyflavone pentaacetate
• UNII-G0B9KJ0VKI
• 5-18-05-00510 (Beilstein Handbook Reference)
• CHEMBL19074
• orb1303683
• SCHEMBL4064499
• BDBM50404746
• MFCD00219362
• NSC115919
• NSC718503
• STL513054
• AKOS000365733
• NSC-718503
• ST024701
• TS-08894
• DS-005360
• HY-124512
• CS-0086730
• E87525
• Q63409134
• 3,5,7-Triacetoxy-2-(3,4-diacetoxyphenyl)-4H-1-benzopyran-4-one
• [2-acetoxy-4-(3,5,7-triacetoxy-4-oxo-chromen-2-yl)phenyl] acetate
• [5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl] acetate
• [5,7-Diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl]acetate
• 2-[3,4-bis(acetyloxy)phenyl]-4-oxo-4H-chromene-3,5,7-triyl triacetate
• 4H-1-Benzopyran-4-one,5,7-tris(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-
• 3,5,7-TRIS(ACETYLOXY)-2-(3,4-BIS(ACETYLOXY)PHENYL)-4H-1-BENZOPYRAN-4-ONE
• 4H-1-benzopyran-4-one,3,5,7-tris(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	-	0.6616	66.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6644	66.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9540	95.40%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8960	89.60%
P-glycoprotein inhibitior	+	0.9217	92.17%
P-glycoprotein substrate	-	0.8371	83.71%
CYP3A4 substrate	+	0.5517	55.17%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8827	88.27%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9872	98.72%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.7177	71.77%
CYP inhibitory promiscuity	+	0.5054	50.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5717	57.17%
Eye corrosion	-	0.9827	98.27%
Eye irritation	-	0.8407	84.07%
Skin irritation	-	0.7923	79.23%
Skin corrosion	-	0.9783	97.83%
Ames mutagenesis	+	0.5136	51.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.8385	83.85%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5229	52.29%
Acute Oral Toxicity (c)	III	0.4839	48.39%
Estrogen receptor binding	+	0.8773	87.73%
Androgen receptor binding	+	0.8509	85.09%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8266	82.66%
Aromatase binding	-	0.5463	54.63%
PPAR gamma	+	0.6429	64.29%
Honey bee toxicity	-	0.7671	76.71%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5949	59.49%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.13%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.35%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.07%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.91%	86.33%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.13%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.05%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.59%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.85%	94.45%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.94%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.96%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.89%	99.17%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.87%	87.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.47%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.27%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.21%	96.09%

Plants that contains it

• Byrsonima coccolobifolia
• Rhamnus

Cross-Links

• PubChem: 14005
• NPASS: NPC177839
• ChEMBL: CHEMBL19074