Hoiamides

Hoiamides
	; Hoiamide A (R = H) and hoiamide B (R = methyl)
	; Hoiamide C (R = ethyl) and hoiamide D (R = H)
Identifiers
3D model (JSmol)	A: Interactive image; B: Interactive image; C: Interactive image; D: Interactive image;
ChEMBL	A: ChEMBL1215858; B: ChEMBL1215859; C: ChEMBL1215860; D: ChEMBL1935083;
ChemSpider	A: 27024431; B: 25059566; C: 25032428; D: 28185012;
PubChem CID	A: 49864267; B: 46919100; C: 46919101; D: 56835050;
	InChI A: InChI=1S/C44H71N5O10S3/c1-14-16-23(6)33(51)25(8)36-24(7)29(57-13)17-30-45-28(18-60-30)38-48-44(12,20-61-38)42-49-43(11,19-62-42)41(56)47-31(22(5)15-2)34(52)26(9)39(54)58-35(21(3)4)37(53)46-32(27(10)50)40(55)59-36/h18,21-27,29,31-36,50-52H,14-17,19-20H2,1-13H3,(H,46,53)(H,47,56)/t22-,23+,24-,25-,26+,27+,29-,31-,32-,33-,34-,35-,36-,43+,44+/m0/s1 Key: AJORQYDPWJZVAU-KCIYAEAGSA-N; B: InChI=1S/C45H73N5O10S3/c1-14-17-24(6)34(52)26(8)37-25(7)30(58-13)18-31-46-29(19-61-31)39-49-45(12,21-62-39)43-50-44(11,20-63-43)42(57)48-32(22(4)15-2)35(53)27(9)40(55)59-36(23(5)16-3)38(54)47-33(28(10)51)41(56)60-37/h19,22-28,30,32-37,51-53H,14-18,20-21H2,1-13H3,(H,47,54)(H,48,57)/t22-,23-,24+,25-,26-,27+,28+,30-,32-,33-,34-,35-,36-,37-,44+,45+/m0/s1 Key: KNGPFNUOXXLKCN-ZNCJFREWSA-N; C: InChI=1S/C37H62N4O7S3/c1-12-15-21(5)29(42)23(7)30(43)22(6)26(47-11)16-27-38-25(17-49-27)32-40-37(10,19-50-32)35-41-36(9,18-51-35)34(46)39-28(20(4)13-2)31(44)24(8)33(45)48-14-3/h17,20-24,26,28-31,42-44H,12-16,18-19H2,1-11H3,(H,39,46)/t20-,21+,22-,23-,24+,26-,28-,29-,30-,31-,36+,37+/m0/s1 Key: STGNMXQTWDOGSE-FUVSMVGWSA-N; D: InChI=1S/C35H58N4O7S3/c1-11-13-19(4)27(40)21(6)28(41)20(5)24(46-10)14-25-36-23(15-47-25)30-38-35(9,17-48-30)33-39-34(8,16-49-33)32(45)37-26(18(3)12-2)29(42)22(7)31(43)44/h15,18-22,24,26-29,40-42H,11-14,16-17H2,1-10H3,(H,37,45)(H,43,44)/t18-,19+,20-,21-,22+,24-,26-,27-,28-,29-,34+,35+/m0/s1 Key: QJJZOVMGNCPTJN-WDSAYIENSA-N;
	SMILES A: CCC[C@@H](C)[C@@H]([C@H](C)[C@@H]1[C@H]([C@H](CC2=NC(=CS2)C3=N[C@](CS3)(C4=N[C@](CS4)(C(=O)N[C@H]([C@H]([C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O1)[C@@H](C)O)C(C)C)C)O)[C@@H](C)CC)C)C)OC)C)O; B: CCC[C@@H](C)[C@@H]([C@H](C)[C@@H]1[C@H]([C@H](CC2=NC(=CS2)C3=N[C@](CS3)(C4=N[C@](CS4)(C(=O)N[C@H]([C@H]([C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O1)[C@@H](C)O)[C@@H](C)CC)C)O)[C@@H](C)CC)C)C)OC)C)O; C: CCC[C@@H](C)[C@@H]([C@H](C)[C@H]([C@@H](C)[C@H](CC1=NC(=CS1)C2=N[C@@](CS2)(C)C3=N[C@@](CS3)(C)C(=O)N[C@@H]([C@@H](C)CC)[C@H]([C@@H](C)C(=O)OCC)O)OC)O)O; D: CCC[C@@H](C)[C@@H]([C@H](C)[C@H]([C@@H](C)[C@H](CC1=NC(=CS1)C2=N[C@@](CS2)(C)C3=N[C@@](CS3)(C)C(=O)N[C@@H]([C@@H](C)CC)[C@H]([C@@H](C)C(=O)O)O)OC)O)O;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The hoiamides are a class of small molecules recently characterized from isolations of secondary metabolites of cyanobacteria that feature a triheterocyclic system. Hoiamide A and B are cyclic while hoiamide C and D are linear. Hoiamide A and B demonstrate neurotoxicity by acting on mammalian voltage gated sodium channels, while hoiamide D shows inhibition of the p53/MDM2 complex. The hoiamides are promising therapeutic targets, making their total synthesis an attractive feat.

Identifiers
Hoiamide A (R = H) and hoiamide B (R = methyl)
Hoiamide C (R = ethyl) and hoiamide D (R = H)
3D model (JSmol)	A: Interactive image B: Interactive image C: Interactive image D: Interactive image
ChEMBL	A: ChEMBL1215858 B: ChEMBL1215859 C: ChEMBL1215860 D: ChEMBL1935083
ChemSpider	A: 27024431 B: 25059566 C: 25032428 D: 28185012
PubChem CID	A: 49864267 B: 46919100 C: 46919101 D: 56835050
InChI A: InChI=1S/C44H71N5O10S3/c1-14-16-23(6)33(51)25(8)36-24(7)29(57-13)17-30-45-28(18-60-30)38-48-44(12,20-61-38)42-49-43(11,19-62-42)41(56)47-31(22(5)15-2)34(52)26(9)39(54)58-35(21(3)4)37(53)46-32(27(10)50)40(55)59-36/h18,21-27,29,31-36,50-52H,14-17,19-20H2,1-13H3,(H,46,53)(H,47,56)/t22-,23+,24-,25-,26+,27+,29-,31-,32-,33-,34-,35-,36-,43+,44+/m0/s1 Key: AJORQYDPWJZVAU-KCIYAEAGSA-N B: InChI=1S/C45H73N5O10S3/c1-14-17-24(6)34(52)26(8)37-25(7)30(58-13)18-31-46-29(19-61-31)39-49-45(12,21-62-39)43-50-44(11,20-63-43)42(57)48-32(22(4)15-2)35(53)27(9)40(55)59-36(23(5)16-3)38(54)47-33(28(10)51)41(56)60-37/h19,22-28,30,32-37,51-53H,14-18,20-21H2,1-13H3,(H,47,54)(H,48,57)/t22-,23-,24+,25-,26-,27+,28+,30-,32-,33-,34-,35-,36-,37-,44+,45+/m0/s1 Key: KNGPFNUOXXLKCN-ZNCJFREWSA-N C: InChI=1S/C37H62N4O7S3/c1-12-15-21(5)29(42)23(7)30(43)22(6)26(47-11)16-27-38-25(17-49-27)32-40-37(10,19-50-32)35-41-36(9,18-51-35)34(46)39-28(20(4)13-2)31(44)24(8)33(45)48-14-3/h17,20-24,26,28-31,42-44H,12-16,18-19H2,1-11H3,(H,39,46)/t20-,21+,22-,23-,24+,26-,28-,29-,30-,31-,36+,37+/m0/s1 Key: STGNMXQTWDOGSE-FUVSMVGWSA-N D: InChI=1S/C35H58N4O7S3/c1-11-13-19(4)27(40)21(6)28(41)20(5)24(46-10)14-25-36-23(15-47-25)30-38-35(9,17-48-30)33-39-34(8,16-49-33)32(45)37-26(18(3)12-2)29(42)22(7)31(43)44/h15,18-22,24,26-29,40-42H,11-14,16-17H2,1-10H3,(H,37,45)(H,43,44)/t18-,19+,20-,21-,22+,24-,26-,27-,28-,29-,34+,35+/m0/s1 Key: QJJZOVMGNCPTJN-WDSAYIENSA-N
SMILES A: CCC[C@@H](C)[C@@H]([C@H](C)[C@@H]1[C@H]([C@H](CC2=NC(=CS2)C3=N[C@](CS3)(C4=N[C@](CS4)(C(=O)N[C@H]([C@H]([C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O1)[C@@H](C)O)C(C)C)C)O)[C@@H](C)CC)C)C)OC)C)O B: CCC[C@@H](C)[C@@H]([C@H](C)[C@@H]1[C@H]([C@H](CC2=NC(=CS2)C3=N[C@](CS3)(C4=N[C@](CS4)(C(=O)N[C@H]([C@H]([C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O1)[C@@H](C)O)[C@@H](C)CC)C)O)[C@@H](C)CC)C)C)OC)C)O C: CCC[C@@H](C)[C@@H]([C@H](C)[C@H]([C@@H](C)[C@H](CC1=NC(=CS1)C2=N[C@@](CS2)(C)C3=N[C@@](CS3)(C)C(=O)N[C@@H]([C@@H](C)CC)[C@H]([C@@H](C)C(=O)OCC)O)OC)O)O D: CCC[C@@H](C)[C@@H]([C@H](C)[C@H]([C@@H](C)[C@H](CC1=NC(=CS1)C2=N[C@@](CS2)(C)C3=N[C@@](CS3)(C)C(=O)N[C@@H]([C@@H](C)CC)[C@H]([C@@H](C)C(=O)O)O)OC)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references