Meleagrin information

Meleagrin
Identifiers
CAS Number	71751-77-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70399;
ChemSpider	23510990;
PubChem CID	115080;
UNII	5780K492K3 ;
CompTox Dashboard (EPA)	DTXSID80891812 ;
	InChI InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1 Key: JTJJJLSLKZFEPJ-ZAYCRUKZSA-N; InChI=1/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1 Key: JTJJJLSLKZFEPJ-ZAYCRUKZBE;
	SMILES CC(C)(C=C)[C@@]12C=C(C(=O)N\3[C@]1(NC(=O)/C3=C\c4c[nH]cn4)N(c5c2cccc5)OC)O;
Properties
Chemical formula	C23H23N5O4
Molar mass	433.468 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Meleagrin and its derivatives such as oxaline are bio-active benzylisoquinoline alkaloids made by various species of Penicillium fungi.^[1] It is similar to other fungal alkaloids, such as Roquefortine C, which is made as an intermediate in the same biosynthetic pathway.

It was suggested to have inhibitory activity on fatty acid synthesis for the bacteria Staphylococcus aureus and Streptococcus pneumoniae.^[2]

^ Du, L; Feng, T; Zhao, B; Li, D; Cai, S; Zhu, T; Wang, F; Xiao, X; Gu, Q (April 2010). "Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities". The Journal of Antibiotics. 63 (4): 165–70. doi:10.1038/ja.2010.11. PMID 20186171. S2CID 12744541.
^ Zheng, CJ; Sohn, MJ; Lee, S; Kim, WG (2013). "Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action". PLOS ONE. 8 (11): e78922. Bibcode:2013PLoSO...878922Z. doi:10.1371/journal.pone.0078922. PMC 3842914. PMID 24312171.

[1] Du, L; Feng, T; Zhao, B; Li, D; Cai, S; Zhu, T; Wang, F; Xiao, X; Gu, Q (April 2010). "Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities". The Journal of Antibiotics. 63 (4): 165–70. doi:10.1038/ja.2010.11. PMID 20186171. S2CID 12744541.

[2] Zheng, CJ; Sohn, MJ; Lee, S; Kim, WG (2013). "Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action". PLOS ONE. 8 (11): e78922. Bibcode:2013PLoSO...878922Z. doi:10.1371/journal.pone.0078922. PMC 3842914. PMID 24312171.

Meleagrin information

and 6 Related for: Meleagrin information

Meleagrin

Penicillium chrysogenum

Oxaline

Penicillium tulipae

Aspergillus brevipes

Fungal isolate

Identifiers

CAS Number	71751-77-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70399
ChemSpider	23510990
PubChem CID	115080
UNII	5780K492K3^Y
CompTox Dashboard (EPA)	DTXSID80891812
InChI InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1 Key: JTJJJLSLKZFEPJ-ZAYCRUKZSA-N InChI=1/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1 Key: JTJJJLSLKZFEPJ-ZAYCRUKZBE
SMILES CC(C)(C=C)[C@@]12C=C(C(=O)N\3[C@]1(NC(=O)/C3=C\c4c[nH]cn4)N(c5c2cccc5)OC)O
Properties
Chemical formula	C₂₃H₂₃N₅O₄
Molar mass	433.468 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references