ID: ALA471282

Max Phase: Preclinical

Molecular Formula: C20H18O11

Molecular Weight: 434.35

Molecule Type: Small molecule

Representations

Synonyms (1): Avicularin
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1c(O[C@@H]2O[C@@H](CO)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12

Standard InChI:  InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1

Standard InChI Key:  BDCDNTVZSILEOY-UXYNSRGZSA-N

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

Properties

Molecular Weight: 434.35

Molecular Weight (Monoisotopic): 434.0849

AlogP: 0.10

#Rotatable Bonds: 4

Polar Surface Area: 190.28

Molecular Species: ACID

HBA: 11

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.37

CX Basic pKa:

CX LogP: 0.49

CX LogD: -0.67

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 2.21

References

1. 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]

2. Tanaka N, Takaishi Y, Shikishima Y, Nakanishi Y, Bastow K, Lee KH, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O..  (2004)  Prenylated benzophenones and xanthones from Hypericum scabrum.,  67  (11): [PMID:15568778] [10.1021/np040024+]

3. Saito K, Matsumoto M, Sekine T, Murakoshi I, Morisaki N, Iwasaki S.  (1989)  Inhibitory Substances from Myriophyllum brasiliense on Growth of Blue-Green Algae,  52  (6): [10.1021/np50066a004]

4. Lale A, Herbert JM, Augereau JM, Billon M, Leconte M, Gleye J..  (1996)  Ability of different flavonoids to inhibit the procoagulant activity of adherent human monocytes.,  59  (3): [PMID:8882428] [10.1021/np960057s]

5. Naeem S, Hylands P, Barlow D..  (2012)  Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase.,  20  (3): [PMID:22261024] [10.1016/j.bmc.2011.12.033]

6. Abramson HN..  (2011)  The lipogenesis pathway as a cancer target.,  54  (16): [PMID:21726077] [10.1021/jm2005805]

7. Bhakat S, Karubiu W, Jayaprakash V, Soliman ME..  (2014)  A perspective on targeting non-structural proteins to combat neglected tropical diseases: Dengue, West Nile and Chikungunya viruses.,  87  [PMID:25305334] [10.1016/j.ejmech.2014.10.010]

8. Feng XH, Wang ZH, Meng DL, Li X..  (2015)  Cytotoxic and antioxidant constituents from the leaves of Psidium guajava.,  25  (10): [PMID:25862199] [10.1016/j.bmcl.2015.03.058]

9. Jin YS..  (2019)  Recent advances in natural antifungal flavonoids and their derivatives.,  29  (19): [PMID:31427220] [10.1016/j.bmcl.2019.07.048]

10. Araki M, Kanda N, Iwata H, Sagae Y, Masuda K, Okuno Y..  (2020)  Identification of a new class of non-electrophilic TRPA1 agonists by a structure-based virtual screening approach.,  30  (11): [PMID:32249116] [10.1016/j.bmcl.2020.127142]

Source

Source(1):

• Scientific Literature