ID: ALA221907

Max Phase: Preclinical

Molecular Formula: C25H24O6

Molecular Weight: 420.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)=CCc1c(-c2ccc(O)cc2O)oc2cc3c(c(O)c2c1=O)C=CC(C)(C)O3

Standard InChI:  InChI=1S/C25H24O6/c1-13(2)5-7-17-23(29)21-20(30-24(17)15-8-6-14(26)11-18(15)27)12-19-16(22(21)28)9-10-25(3,4)31-19/h5-6,8-12,26-28H,7H2,1-4H3

Standard InChI Key:  XIWCDUHPYMOFIL-UHFFFAOYSA-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: 420.46

Molecular Weight (Monoisotopic): 420.1573

AlogP: 5.27

#Rotatable Bonds: 3

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.19

CX Basic pKa:

CX LogP: 5.22

CX LogD: 4.76

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: 2.63

References

1. Park KH, Park YD, Han JM, Im KR, Lee BW, Jeong IY, Jeong TS, Lee WS..  (2006)  Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata.,  16  (21): [PMID:16919944] [10.1016/j.bmcl.2006.08.032]

2. Hwang JH, Hong SS, Han XH, Hwang JS, Lee D, Lee H, Yun YP, Kim Y, Ro JS, Hwang BY..  (2007)  Prenylated xanthones from the root bark of Cudrania tricuspidata.,  70  (7): [PMID:17608532] [10.1021/np070059k]

3. Ryu YB, Curtis-Long MJ, Lee JW, Ryu HW, Kim JY, Lee WS, Park KH..  (2009)  Structural characteristics of flavanones and flavones from Cudrania tricuspidata for neuraminidase inhibition.,  19  (17): [PMID:19660948] [10.1016/j.bmcl.2009.07.098]

4. PubChem BioAssay data set, 

5. Hošek J, Bartos M, Chudík S, Dall'Acqua S, Innocenti G, Kartal M, Kokoška L, Kollár P, Kutil Z, Landa P, Marek R, Závalová V, Žemlička M, Šmejkal K..  (2011)  Natural compound cudraflavone B shows promising anti-inflammatory properties in vitro.,  74  (4): [PMID:21319773] [10.1021/np100638h]

6. Hošek J, Toniolo A, Neuwirth O, Bolego C..  (2013)  Prenylated and geranylated flavonoids increase production of reactive oxygen species in mouse macrophages but inhibit the inflammatory response.,  76  (9): [PMID:23947936] [10.1021/np400242e]

7. Zelová H, Hanáková Z, Čermáková Z, Šmejkal K, Dalĺ Acqua S, Babula P, Cvačka J, Hošek J..  (2014)  Evaluation of anti-inflammatory activity of prenylated substances isolated from Morus alba and Morus nigra.,  77  (6): [PMID:24901948] [10.1021/np401025f]

8. Toume K, Habu T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M..  (2015)  Prenylated flavonoids and resveratrol derivatives isolated from Artocarpus communis with the ability to overcome TRAIL resistance.,  78  (1): [PMID:25537111] [10.1021/np500734t]

9. Kishore N, Kumar P, Shanker K, Verma AK..  (2019)  Human disorders associated with inflammation and the evolving role of natural products to overcome.,  179  [PMID:31255927] [10.1016/j.ejmech.2019.06.034]

10. Qu KJ, Wang B, Jiang CS, Xie BG, Liu AH, Li SW, Guo YW, Li J, Mao SC..  (2021)  Rearranged Diels-Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra.,  84  (8.0): [PMID:34279099] [10.1021/acs.jnatprod.1c00403]

11. Dong H, Wu M, Xiang S, Song T, Li Y, Long B, Feng C, Shi Z..  (2022)  Total Syntheses and Antibacterial Evaluations of Neocyclomorusin and Related Flavones.,  85  (9.0): [PMID:36062892] [10.1021/acs.jnatprod.2c00658]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays