Acetic acid 5,7-diacetoxy-2-(3,4-diacetoxy-phenyl)-4-oxo-4H-chromen-3-yl ester

ID: ALA19074

Chembl Id: CHEMBL19074

Cas Number: 1064-06-8

PubChem CID: 14005

Max Phase: Preclinical

Molecular Formula: C25H20O12

Molecular Weight: 512.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-115919 | Quercetin pentaacetate|1064-06-8|Pentaacetylquercetin|Quercetin acetate|3,3',4',5,7-Pentaacetoxyflavone|NSC-115919|G0B9KJ0VKI|QUERCETINPENTAACETATE|[2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate|4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-(3,4-bis(acetyloxy)phenyl)-|FLAVONE, 3,3',4',5,7-PENTAHYDROXY-, PENTAACETATE|NSC 115919|BRN 0380215|3,3',4',5,7-Pentahydroxyflavone pentaacetate|UNII-G0B9KJ0VKI|5-18-05-00510 (Beilstein Handbook Reference)|CHEMBL19074|SCHEMShow More⌵

Canonical SMILES:  CC(=O)Oc1cc(OC(C)=O)c2c(=O)c(OC(C)=O)c(-c3ccc(OC(C)=O)c(OC(C)=O)c3)oc2c1

Standard 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

Standard InChI Key:  JQUHMSXLZZWRHU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA19074

   PENTAACETYLQUERCETIN

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 512.42

Molecular Weight (Monoisotopic): 512.0955

AlogP: 3.09

#Rotatable Bonds: 6

Polar Surface Area: 161.71

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.06

CX LogD: 1.06

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.35

Np Likeness Score: 0.68

References

1. Picq M, Prigent AF, Némoz G, André AC, Pacheco H..  (1982)  Pentasubstituted quercetin analogues as selective inhibitors of particulate 3':5'-cyclic-AMP phosphodiesterase from rat brain.,  25  (10): [PMID:6292419] [10.1021/jm00352a019]

2. Kohli E, Raj HG, Kumari R, Rohil V, Kaushik NK, Prasad AK, Parmar VS..  (2002)  Comparison of the prevention of aflatoxin b(1)-induced genotoxicity by quercetin and quercetin pentaacetate.,  12  (18): [PMID:12182864] [10.1016/s0960-894x(02)00478-x]

3. Biasutto L, Marotta E, De Marchi U, Zoratti M, Paradisi C..  (2007)  Ester-based precursors to increase the bioavailability of quercetin.,  50  (2): [PMID:17228866] [10.1021/jm060912x]

4. Hayashi T, Sawa K, Kawasaki M, Arisawa M, Shimizu M, Morita N..  (1988)  Inhibition of cow's milk xanthine oxidase by flavonoids.,  51  (2): [PMID:3379415] [10.1021/np50056a030]

5. Edwards JM, Raffauf RF, Le Quesne PW..  (1979)  Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones.,  42  (1): [PMID:469554] [10.1021/np50001a002]

6. Chung MI, Gan KH, Lin CN, Ko FN, Teng CM..  (1993)  Antiplatelet effects and vasorelaxing action of some constituents of Formosan plants.,  56  (6): [PMID:8350094] [10.1021/np50096a018]

7. Marín C, Boutaleb-Charki S, Díaz JG, Huertas O, Rosales MJ, Pérez-Cordon G, Guitierrez-Sánchez R, Sánchez-Moreno M..  (2009)  Antileishmaniasis activity of flavonoids from Consolida oliveriana.,  72  (6): [PMID:19489596] [10.1021/np8008122]

8. Carver JA, Duggan PJ, Ecroyd H, Liu Y, Meyer AG, Tranberg CE..  (2010)  Carboxymethylated-kappa-casein: a convenient tool for the identification of polyphenolic inhibitors of amyloid fibril formation.,  18  (1): [PMID:19931462] [10.1016/j.bmc.2009.10.063]

9. de Sousa LR, Ramalho SD, Burger MC, Nebo L, Fernandes JB, da Silva MF, Iemma MR, Corrêa CJ, de Souza DH, Lima MI, Vieira PC..  (2014)  Isolation of arginase inhibitors from the bioactivity-guided fractionation of Byrsonima coccolobifolia leaves and stems.,  77  (2): [PMID:24521209] [10.1021/np400717m]

Source

Source(1):

• Scientific Literature