Dragomabin

Dragomabin
Identifiers
CAS Number	(revised): 942039-60-3;
3D model (JSmol)	(revised): Interactive image;
ChEBI	(originally proposed): CHEBI:65583;
ChEMBL	(originally proposed): ChEMBL391000;
ChemSpider	(originally proposed): 20568904;
PubChem CID	(originally proposed): 16737469;
CompTox Dashboard (EPA)	DTXSID501045725 ;
	InChI (revised): InChI=1S/C37H51N5O6/c1-9-10-11-13-16-25(2)35(45)42(7)32(24-28-17-14-12-15-18-28)34(44)39-26(3)36(46)40(5)27(4)37(47)41(6)31(33(38)43)23-29-19-21-30(48-8)22-20-29/h1,12,14-15,17-22,25-27,31-32H,10-11,13,16,23-24H2,2-8H3,(H2,38,43)(H,39,44)/t25-,26+,27+,31+,32+/m1/s1 Key: JAYHQHZOWYDLDQ-WLVJZVJWSA-N;
	SMILES (revised): [C@@H](CC1=CC=CC=C1)(N(C([C@@H](CCCCC#C)C)=O)C)C(N[C@H](C(N([C@H](C(N([C@@H](CC2=CC=C(OC)C=C2)C(N)=O)C)=O)C)C)=O)C)=O;
Properties
Chemical formula	C37H51N5O6
Molar mass	661.844 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

Dragomabin is a lipopeptide isolated from the marine cyanobacteria Lyngbya majuscula.^[1] It has in vitro antimalarial activity.^[1] In 2018, a laboratory synthesis of dragomabin was reported.^[2] The synthesis identified a misassignment of the configuration of the stereogenic center on the alkyne-bearing fragment and it was revised from (S) to (R).^[2]

References

^ ^a ^b McPhail, Kerry L.; Correa, Jhonny; Linington, Roger G.; González, José; Ortega-Barría, Eduardo; Capson, Todd L.; Gerwick, William H. (June 2007). "Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium". Journal of Natural Products. 70 (6): 984–988. doi:10.1021/np0700772. PMC 2745555. PMID 17441769.
^ ^a ^b Ye, Baijun; Jiang, Peng; Zhang, Tingrong; Sun, Yuanjun; Hao, Xin; Cui, Yingjun; Wang, Liang; Chen, Yue (2018). "Total Synthesis of the Highly N-Methylated Peptides Carmabin a and Dragomabin". Marine Drugs. 16 (9): 338. doi:10.3390/md16090338. PMC 6164609. PMID 30227592.

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[McPhail-1] McPhail, Kerry L.; Correa, Jhonny; Linington, Roger G.; González, José; Ortega-Barría, Eduardo; Capson, Todd L.; Gerwick, William H. (June 2007). "Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium". Journal of Natural Products. 70 (6): 984–988. doi:10.1021/np0700772. PMC 2745555. PMID 17441769.

[Ye-2] Ye, Baijun; Jiang, Peng; Zhang, Tingrong; Sun, Yuanjun; Hao, Xin; Cui, Yingjun; Wang, Liang; Chen, Yue (2018). "Total Synthesis of the Highly N-Methylated Peptides Carmabin a and Dragomabin". Marine Drugs. 16 (9): 338. doi:10.3390/md16090338. PMC 6164609. PMID 30227592.

[1]

[2]

Identifiers

CAS Number	(revised): 942039-60-3
3D model (JSmol)	(revised): Interactive image
ChEBI	(originally proposed): CHEBI:65583
ChEMBL	(originally proposed): ChEMBL391000
ChemSpider	(originally proposed): 20568904
PubChem CID	(originally proposed): 16737469
CompTox Dashboard (EPA)	DTXSID501045725
InChI (revised): InChI=1S/C37H51N5O6/c1-9-10-11-13-16-25(2)35(45)42(7)32(24-28-17-14-12-15-18-28)34(44)39-26(3)36(46)40(5)27(4)37(47)41(6)31(33(38)43)23-29-19-21-30(48-8)22-20-29/h1,12,14-15,17-22,25-27,31-32H,10-11,13,16,23-24H2,2-8H3,(H2,38,43)(H,39,44)/t25-,26+,27+,31+,32+/m1/s1 Key: JAYHQHZOWYDLDQ-WLVJZVJWSA-N
SMILES (revised): [C@@H](CC1=CC=CC=C1)(N(C([C@@H](CCCCC#C)C)=O)C)C(N[C@H](C(N([C@H](C(N([C@@H](CC2=CC=C(OC)C=C2)C(N)=O)C)=O)C)C)=O)C)=O
Properties
Chemical formula	C₃₇H₅₁N₅O₆
Molar mass	661.844 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