Chemistry:Mirabamide

Mirabamide
	; Mirabamide A–D
Identifiers
3D model (JSmol)	A: Interactive image; B: Interactive image; C: Interactive image; D: Interactive image; E: Interactive image;
ChEBI	C: CHEBI:68407; E: CHEBI:68403;
ChEMBL	A: ChEMBL429406; B: ChEMBL249470; D: ChEMBL398500; E: ChEMBL1689426;
ChemSpider	B: 29213836; E: 26393785;
PubChem CID	A: 24179735; B: 24179622; C: 24179849; D: 24179734; E: 51041750;
	InChI A: InChI=1S/C72H114ClN13O25/c1-17-32(4)26-33(5)18-23-46(89)72(13,106)71(105)77-29-48(91)80-51(38(10)87)64(99)82-50(36(8)74)63(98)81-49(34(6)35(7)60(75)95)62(97)83-52-58(31(2)3)111-69(104)45-27-42(73)24-25-86(45)68(103)53(59(108-16)41-19-21-43(22-20-41)110-70-57(94)56(93)55(92)40(12)109-70)84-66(101)54(39(11)88)85(14)67(102)37(9)78-47(90)28-76-61(96)44(30-107-15)79-65(52)100/h18-23,26,31-32,34-40,42,44-46,49-59,70,87-89,92-94,106H,17,24-25,27-30,74H2,1-16H3,(H2,75,95)(H,76,96)(H,77,105)(H,78,90)(H,79,100)(H,80,91)(H,81,98)(H,82,99)(H,83,97)(H,84,101)/b23-18-,33-26+/t32?,34-,35+,36+,37-,38+,39+,40-,42-,44+,45-,46?,49-,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Computed by InChI 1.0.6 (PubChem release 2021.05.07) Key: PYYXFJVIXGKIPV-IATOIQLISA-N; B: InChI=1S/C72H111ClN12O25/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)76-30-49(90)80-51(38(10)86)64(98)78-44(18-2)62(96)81-50(35(7)36(8)60(74)94)63(97)82-52-58(32(3)4)110-69(103)46-28-42(73)25-26-85(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)83-66(100)54(39(11)87)84(14)67(101)37(9)77-48(89)29-75-61(95)45(31-106-15)79-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,86-88,91-93,105H,17,25-26,28-31H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,98)(H,79,99)(H,80,90)(H,81,96)(H,82,97)(H,83,100)/b24-19-,34-27+,44-18-/t33?,35-,36+,37-,38+,39+,40-,42-,45+,46-,47?,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: UHQCAXFLMDVFDC-NAUJABJQSA-N; C: InChI=1S/C66H104ClN13O21/c1-16-31(4)25-32(5)17-22-44(84)66(12,98)65(97)71-28-46(86)74-49(37(10)81)59(91)76-48(35(8)68)58(90)75-47(33(6)34(7)55(69)87)57(89)77-50-53(30(2)3)101-64(96)43-26-40(67)23-24-80(43)63(95)51(54(100-15)39-18-20-41(83)21-19-39)78-61(93)52(38(11)82)79(13)62(94)36(9)72-45(85)27-70-56(88)42(29-99-14)73-60(50)92/h17-22,25,30-31,33-38,40,42-44,47-54,81-84,98H,16,23-24,26-29,68H2,1-15H3,(H2,69,87)(H,70,88)(H,71,97)(H,72,85)(H,73,92)(H,74,86)(H,75,90)(H,76,91)(H,77,89)(H,78,93)/b22-17-,32-25+/t31?,33-,34+,35+,36-,37+,38+,40-,42+,43-,44?,47-,48-,49?,50+,51+,52-,53+,54+,66?/m0/s1 Key: VEJZPSFCBFZXDK-QGPFMVGKSA-N; D: InChI=1S/C72H115N13O25/c1-17-33(4)28-34(5)21-26-46(88)72(13,105)71(104)76-30-48(90)79-51(39(10)86)64(98)81-50(37(8)73)63(97)80-49(35(6)36(7)60(74)94)62(96)82-52-58(32(2)3)110-69(103)45-20-18-19-27-85(45)68(102)53(59(107-16)42-22-24-43(25-23-42)109-70-57(93)56(92)55(91)41(12)108-70)83-66(100)54(40(11)87)84(14)67(101)38(9)77-47(89)29-75-61(95)44(31-106-15)78-65(52)99/h21-26,28,32-33,35-41,44-46,49-59,70,86-88,91-93,105H,17-20,27,29-31,73H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,99)(H,79,90)(H,80,97)(H,81,98)(H,82,96)(H,83,100)/b26-21-,34-28+/t33?,35-,36+,37+,38-,39+,40+,41-,44+,45-,46?,49-,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: NAEQWXPETBQBMW-WVBSTJMVSA-N; E: InChI=1S/C72H112ClN13O24/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)77-30-49(90)79-44(18-2)62(96)82-51(37(9)74)64(98)81-50(35(7)36(8)60(75)94)63(97)83-52-58(32(3)4)110-69(103)46-28-42(73)25-26-86(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)84-66(100)54(39(11)87)85(14)67(101)38(10)78-48(89)29-76-61(95)45(31-106-15)80-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,87-88,91-93,105H,17,25-26,28-31,74H2,1-16H3,(H2,75,94)(H,76,95)(H,77,104)(H,78,89)(H,79,90)(H,80,99)(H,81,98)(H,82,96)(H,83,97)(H,84,100)/b24-19-,34-27+,44-18-/t33?,35-,36+,37-,38-,39+,40-,42-,45+,46-,47?,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: APTOZTHRCLKEEQ-OJHSLUOMSA-N;
	SMILES A: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@H](CCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)Cl)C(C)C)O)O; B: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N/C(=C\C)/C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@H](CCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)Cl)C(C)C)O)O; C: CCC(C)\C=C(C)\C=C/C(O)C(C)(O)C(=O)NCC(=O)NC([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)c1ccc(O)cc1)C(C)C; D: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2CCCCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)C(C)C)O)O; E: CCC(C)\C=C(C)\C=C/C(O)C(C)(O)C(=O)NCC(=O)N\C(=C/C)C(=O)N[C@@H]([C@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)c1ccc(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1)C(C)C;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Mirabamides are sea sponge isolates that inhibit HIV-1 fusion.^[1] Variants A to D are known from Siliquariaspongia mirabilis and E throuh H are derived from Stelletta clavosa.^[2] Mirabamides have a macrocyclic region closed through an ester bond between the C-terminus and a 𝛽-hydroxyl group, and terminated with a polyketide moiety or a more simple branched aliphatic acid.^[3]

Mirabamide G is a fusion of several amino acids: 2,3 diamino butanoic acid, 3-hydroxyleucine, N-methylthreonine, 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid, 3-methoxy alanine, β-methoxytyrosine, 3,4-dimethylglutamine.^[4]

References

↑ Plaza, A; Gustchina, E; Baker, HL; Kelly, M; Bewley, CA (2007). "Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion". Journal of Natural Products 70 (11): 1753–60. doi:10.1021/np070306k. PMID 17963357.
↑ Lu, Zhenyu; Van Wagoner, Ryan M.; Harper, Mary Kay; Baker, Heather L.; Hooper, John N. A.; Bewley, Carole A.; Ireland, Chris M. (25 February 2011). "Mirabamides E−H, HIV-Inhibitory Depsipeptides from the Sponge Stelletta clavosa". Journal of Natural Products 74 (2): 185–193. doi:10.1021/np100613p. PMID 21280591.
↑ Frau, Juan; Flores-Holguín, Norma; Glossman-Mitnik, Daniel (28 August 2018). "Chemical Reactivity Properties, pKa Values, AGEs Inhibitor Abilities and Bioactivity Scores of the Mirabamides A–H Peptides of Marine Origin Studied by Means of Conceptual DFT". Marine Drugs 16 (9): 302. doi:10.3390/md16090302. PMID 30154377.
↑ Lazcano-Perez, Fernando; Roman-Gonzalez, Sergio A.; Sanchez-Puig, Nuria; Espinosa, Roberto Arreguin- (2012). "Bioactive Peptides from Marine Organisms: A Short Overview". Protein and Peptide Letters 19 (7): 700–707. doi:10.2174/092986612800793208. PMID 22489781.

attribution: Contains text from the CC/BY/4.0 licensed "Chemical Reactivity Properties, pK_a Values, AGEs Inhibitor Abilities and Bioactivity Scores of the Mirabamides A–H Peptides of Marine Origin Studied by Means of Conceptual DFT" by Lazcano-Perez et al.

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[1] Plaza, A; Gustchina, E; Baker, HL; Kelly, M; Bewley, CA (2007). "Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion". Journal of Natural Products 70 (11): 1753–60. doi:10.1021/np070306k. PMID 17963357.

[2] Lu, Zhenyu; Van Wagoner, Ryan M.; Harper, Mary Kay; Baker, Heather L.; Hooper, John N. A.; Bewley, Carole A.; Ireland, Chris M. (25 February 2011). "Mirabamides E−H, HIV-Inhibitory Depsipeptides from the Sponge Stelletta clavosa". Journal of Natural Products 74 (2): 185–193. doi:10.1021/np100613p. PMID 21280591.

[3] Frau, Juan; Flores-Holguín, Norma; Glossman-Mitnik, Daniel (28 August 2018). "Chemical Reactivity Properties, pKa Values, AGEs Inhibitor Abilities and Bioactivity Scores of the Mirabamides A–H Peptides of Marine Origin Studied by Means of Conceptual DFT". Marine Drugs 16 (9): 302. doi:10.3390/md16090302. PMID 30154377.

[4] Lazcano-Perez, Fernando; Roman-Gonzalez, Sergio A.; Sanchez-Puig, Nuria; Espinosa, Roberto Arreguin- (2012). "Bioactive Peptides from Marine Organisms: A Short Overview". Protein and Peptide Letters 19 (7): 700–707. doi:10.2174/092986612800793208. PMID 22489781.

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Chemistry:Mirabamide

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Identifiers
Mirabamide A–D
3D model (JSmol)	A: Interactive image B: Interactive image C: Interactive image D: Interactive image E: Interactive image
ChEBI	C: CHEBI:68407 E: CHEBI:68403
ChEMBL	A: ChEMBL429406 B: ChEMBL249470 D: ChEMBL398500 E: ChEMBL1689426
ChemSpider	B: 29213836 E: 26393785
PubChem CID	A: 24179735 B: 24179622 C: 24179849 D: 24179734 E: 51041750
InChI A: InChI=1S/C72H114ClN13O25/c1-17-32(4)26-33(5)18-23-46(89)72(13,106)71(105)77-29-48(91)80-51(38(10)87)64(99)82-50(36(8)74)63(98)81-49(34(6)35(7)60(75)95)62(97)83-52-58(31(2)3)111-69(104)45-27-42(73)24-25-86(45)68(103)53(59(108-16)41-19-21-43(22-20-41)110-70-57(94)56(93)55(92)40(12)109-70)84-66(101)54(39(11)88)85(14)67(102)37(9)78-47(90)28-76-61(96)44(30-107-15)79-65(52)100/h18-23,26,31-32,34-40,42,44-46,49-59,70,87-89,92-94,106H,17,24-25,27-30,74H2,1-16H3,(H2,75,95)(H,76,96)(H,77,105)(H,78,90)(H,79,100)(H,80,91)(H,81,98)(H,82,99)(H,83,97)(H,84,101)/b23-18-,33-26+/t32?,34-,35+,36+,37-,38+,39+,40-,42-,44+,45-,46?,49-,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Computed by InChI 1.0.6 (PubChem release 2021.05.07) Key: PYYXFJVIXGKIPV-IATOIQLISA-N B: InChI=1S/C72H111ClN12O25/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)76-30-49(90)80-51(38(10)86)64(98)78-44(18-2)62(96)81-50(35(7)36(8)60(74)94)63(97)82-52-58(32(3)4)110-69(103)46-28-42(73)25-26-85(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)83-66(100)54(39(11)87)84(14)67(101)37(9)77-48(89)29-75-61(95)45(31-106-15)79-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,86-88,91-93,105H,17,25-26,28-31H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,98)(H,79,99)(H,80,90)(H,81,96)(H,82,97)(H,83,100)/b24-19-,34-27+,44-18-/t33?,35-,36+,37-,38+,39+,40-,42-,45+,46-,47?,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: UHQCAXFLMDVFDC-NAUJABJQSA-N C: InChI=1S/C66H104ClN13O21/c1-16-31(4)25-32(5)17-22-44(84)66(12,98)65(97)71-28-46(86)74-49(37(10)81)59(91)76-48(35(8)68)58(90)75-47(33(6)34(7)55(69)87)57(89)77-50-53(30(2)3)101-64(96)43-26-40(67)23-24-80(43)63(95)51(54(100-15)39-18-20-41(83)21-19-39)78-61(93)52(38(11)82)79(13)62(94)36(9)72-45(85)27-70-56(88)42(29-99-14)73-60(50)92/h17-22,25,30-31,33-38,40,42-44,47-54,81-84,98H,16,23-24,26-29,68H2,1-15H3,(H2,69,87)(H,70,88)(H,71,97)(H,72,85)(H,73,92)(H,74,86)(H,75,90)(H,76,91)(H,77,89)(H,78,93)/b22-17-,32-25+/t31?,33-,34+,35+,36-,37+,38+,40-,42+,43-,44?,47-,48-,49?,50+,51+,52-,53+,54+,66?/m0/s1 Key: VEJZPSFCBFZXDK-QGPFMVGKSA-N D: InChI=1S/C72H115N13O25/c1-17-33(4)28-34(5)21-26-46(88)72(13,105)71(104)76-30-48(90)79-51(39(10)86)64(98)81-50(37(8)73)63(97)80-49(35(6)36(7)60(74)94)62(96)82-52-58(32(2)3)110-69(103)45-20-18-19-27-85(45)68(102)53(59(107-16)42-22-24-43(25-23-42)109-70-57(93)56(92)55(91)41(12)108-70)83-66(100)54(40(11)87)84(14)67(101)38(9)77-47(89)29-75-61(95)44(31-106-15)78-65(52)99/h21-26,28,32-33,35-41,44-46,49-59,70,86-88,91-93,105H,17-20,27,29-31,73H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,99)(H,79,90)(H,80,97)(H,81,98)(H,82,96)(H,83,100)/b26-21-,34-28+/t33?,35-,36+,37+,38-,39+,40+,41-,44+,45-,46?,49-,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: NAEQWXPETBQBMW-WVBSTJMVSA-N E: InChI=1S/C72H112ClN13O24/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)77-30-49(90)79-44(18-2)62(96)82-51(37(9)74)64(98)81-50(35(7)36(8)60(75)94)63(97)83-52-58(32(3)4)110-69(103)46-28-42(73)25-26-86(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)84-66(100)54(39(11)87)85(14)67(101)38(10)78-48(89)29-76-61(95)45(31-106-15)80-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,87-88,91-93,105H,17,25-26,28-31,74H2,1-16H3,(H2,75,94)(H,76,95)(H,77,104)(H,78,89)(H,79,90)(H,80,99)(H,81,98)(H,82,96)(H,83,97)(H,84,100)/b24-19-,34-27+,44-18-/t33?,35-,36+,37-,38-,39+,40-,42-,45+,46-,47?,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1 Key: APTOZTHRCLKEEQ-OJHSLUOMSA-N
SMILES A: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@H](CCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)Cl)C(C)C)O)O B: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N/C(=C\C)/C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@H](CCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)Cl)C(C)C)O)O C: CCC(C)\C=C(C)\C=C/C(O)C(C)(O)C(=O)NCC(=O)NC([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)c1ccc(O)cc1)C(C)C D: CCC(C)/C=C(\C)/C=C\C(C(C)(C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(=O)N)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2CCCCN2C(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H](NC1=O)COC)C)C)[C@@H](C)O)[C@@H](C3=CC=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC)C(C)C)O)O E: CCC(C)\C=C(C)\C=C/C(O)C(C)(O)C(=O)NCC(=O)N\C(=C/C)C(=O)N[C@@H]([C@H](C)N)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)c1ccc(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1)C(C)C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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