5,6-dehydrokawain

ID: ALA254218

Chembl Id: CHEMBL254218

Cas Number: 15345-89-8

PubChem CID: 5273621

Product Number: D132399

Max Phase: Preclinical

Molecular Formula: C14H12O3

Molecular Weight: 228.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5,6-Dehydrokawain | 5,6-Dehydrokawin | Desmethoxyyangonin | Desmethoxyyangonin|5,6-Dehydrokawain|Demethoxyyangonin|15345-89-8|Desmethoxy Yangonin|5,6-Dehydrokavain|(E)-4-Methoxy-6-styryl-2H-pyran-2-one|1952-41-6|Yangonin, demethoxy-|4-Methoxy-6-styryl-2H-pyran-2-one|NSC 112161|F2MBQ8QRUN|UNII-F2MBQ8QRUN|2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-phenylethenyl]-|4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one|2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)-|CCRIS 9369|DTXSID4033390|(E)-4-Methoxy-6-(2-pShow More⌵

Canonical SMILES:  COc1cc(/C=C/c2ccccc2)oc(=O)c1

Standard InChI:  InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

Standard InChI Key:  DKKJNZYHGRUXBS-BQYQJAHWSA-N

Alternative Forms

1. Parent:

   

   ALA254218

   DESMETHOXYYANGONIN

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

Calculated Properties

Molecular Weight: 228.25

Molecular Weight (Monoisotopic): 228.0786

AlogP: 2.82

#Rotatable Bonds: 3

Polar Surface Area: 39.44

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.81

Np Likeness Score: 0.61

References

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3. Ali MS, Tezuka Y, Awale S, Banskota AH, Kadota S..  (2001)  Six new diarylheptanoids from the seeds of Alpinia blepharocalyx.,  64  (3): [PMID:11277741] [10.1021/np000496y]

4. Shaik AA, Hermanson DL, Xing C..  (2009)  Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.,  19  (19): [PMID:19716299] [10.1016/j.bmcl.2009.08.003]

5. Ohtsuki T, Kikuchi H, Koyano T, Kowithayakorn T, Sakai T, Ishibashi M..  (2009)  Death receptor 5 promoter-enhancing compounds isolated from Catimbium speciosum and their enhancement effect on TRAIL-induced apoptosis.,  17  (18): [PMID:19682913] [10.1016/j.bmc.2009.07.041]

6. PubChem BioAssay data set, 

7. McCracken ST, Kaiser M, Boshoff HI, Boyd PD, Copp BR..  (2012)  Synthesis and antimalarial and antituberculosis activities of a series of natural and unnatural 4-methoxy-6-styryl-pyran-2-ones, dihydro analogues and photo-dimers.,  20  (4): [PMID:22285027] [10.1016/j.bmc.2011.12.053]

8. Iwai Y, Murakami K, Gomi Y, Hashimoto T, Asakawa Y, Okuno Y, Ishikawa T, Hatakeyama D, Echigo N, Kuzuhara T..  (2011)  Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.,  6  (5): [PMID:21625478] [10.1371/journal.pone.0019825]

9. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

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11. Tawata S, Taira S, Kobamoto N, Ishihara M, Toyama S..  (1996)  Syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives.,  60  (10): [PMID:8987662] [10.1271/bbb.60.1643]

12. Ahmad I, Thakur JP, Chanda D, Saikia D, Khan F, Dixit S, Kumar A, Konwar R, Negi AS, Gupta A..  (2013)  Syntheses of lipophilic chalcones and their conformationally restricted analogues as antitubercular agents.,  23  (5): [PMID:23369537] [10.1016/j.bmcl.2012.12.096]

13. PubChem BioAssay data set, 

14. Kumagai M, Nishikawa K, Mishima T, Yoshida I, Ide M, Koizumi K, Nakamura M, Morimoto Y..  (2017)  Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms.,  27  (11): [PMID:28427810] [10.1016/j.bmcl.2017.04.016]

15. Karhu E, Isojärvi J, Vuorela P, Hanski L, Fallarero A..  (2017)  Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.,  80  (10): [PMID:29043803] [10.1021/acs.jnatprod.6b01052]

16. Gény C, Abou Samra A, Retailleau P, Iorga BI, Nedev H, Awang K, Roussi F, Litaudon M, Dumontet V..  (2017)  (+)- and (-)-Ecarlottones, Uncommon Chalconoids from Fissistigma latifolium with Pro-Apoptotic Activity.,  80  (12): [PMID:29160716] [10.1021/acs.jnatprod.7b00494]

17. Matsumoto T, Kitagawa T, Imahori D, Matsuzaki A, Saito Y, Ohta T, Yoshida T, Nakayama Y, Ashihara E, Watanabe T..  (2021)  Linderapyrone: A Wnt signal inhibitor isolated from Lindera umbellata.,  45  [PMID:34062253] [10.1016/j.bmcl.2021.128161]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays