ID: ALA72617

Max Phase: Preclinical

Molecular Formula: C26H28O6

Molecular Weight: 436.50

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  COc1cc2oc(-c3ccc(O)cc3O)c(CC=C(C)C)c(=O)c2c(O)c1/C=C/C(C)C

Standard InChI:  InChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+

Standard InChI Key:  KRGDFVQWQJIMEK-RMKNXTFCSA-N

Molecule Features

Natural Product: No

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: 436.50

Molecular Weight (Monoisotopic): 436.1886

AlogP: 5.76

#Rotatable Bonds: 6

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: 7.24

CX Basic pKa:

CX LogP: 6.01

CX LogD: 5.59

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: 1.98

References

1. Karton Y, Jiang JL, Ji XD, Melman N, Olah ME, Stiles GL, Jacobson KA..  (1996)  Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.,  39  (12): [PMID:8691424] [10.1021/jm950923i]

2. Wang YH, Hou AJ, Chen L, Chen DF, Sun HD, Zhao QS, Bastow KF, Nakanish Y, Wang XH, Lee KH..  (2004)  New isoprenylated flavones, artochamins A--E, and cytotoxic principles from Artocarpus chama.,  67  (5): [PMID:15165133] [10.1021/np030467y]

3. Lin CN, Lu CM, Lin HC, Fang SC, Shieh BJ, Hsu MF, Wang JP, Ko FN, Teng CM..  (1996)  Novel antiplatelet constituents from formosan moraceous plants.,  59  (9): [PMID:8864236] [10.1021/np960376j]

4. Han AR, Kang YJ, Windono T, Lee SK, Seo EK..  (2006)  Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production.,  69  (4): [PMID:16643064] [10.1021/np0600346]

5. PubChem BioAssay data set, 

6. Nguyen MTT, Le TH, Nguyen HX, Dang PH, Do TNV, Abe M, Takagi R, Nguyen NT..  (2017)  Artocarmins G-M, Prenylated 4-Chromenones from the Stems of Artocarpus rigida and Their Tyrosinase Inhibitory Activities.,  80  (12): [PMID:29227656] [10.1021/acs.jnatprod.7b00453]

7. Meenu MT, Kaul G, Akhir A, Shukla M, Radhakrishnan KV, Chopra S..  (2022)  Developing the Natural Prenylflavone Artocarpin from Artocarpus hirsutus as a Potential Lead Targeting Pathogenic, Multidrug-Resistant Staphylococcus aureus, Persisters and Biofilms with No Detectable Resistance.,  85  (10.0): [PMID:36222797] [10.1021/acs.jnatprod.2c00621]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays