PRD_002430
Summary
| Name: | Darobactin 9 |
| Formula: | C49 H57 N12 O12 |
| Fomular weight: | 1006.05 |
| Component type: | peptide-like |
| Polymer sequences: | 0AF, ASN, TRP, SER, LYS, SER, TRP |
| Non-polymer components: | |
| BIRD class: | Antibiotic |
| Represented as: | polymer |
| Compound Details: | The native darobactin A producer Photorhabdus khanii HGB1456 shows very limited production under laboratory cultivation conditions. Hence scientists designed heterologous expression of the darobactin biosynthetic gene cluster (BGC) in Escherichia coli. Rational design of darA variant resulted in the production of new 'non-natural' darobactin derivatives. One of the non-natural compounds, darobactin 9, was more potent than darobactin A. |
| Program | Version | Name |
| OpenEye OEToolkits | 3.1.0.0 | 3-[(17~{S},20~{S},23~{S},26~{S},29~{S})-17-azanyl-20-(2-azanyl-2-oxidanylidene-ethyl)-26-(hydroxymethyl)-29-[[(2~{S})-1-[[(2~{S})-3-(1~{H}-indol-3-yl)-1-oxidanyl-1-oxidanylidene-propan-2-yl]amino]-3-oxidanyl-1-oxidanylidene-propan-2-yl]carbamoyl]-18,21,24,27-tetrakis(oxidanylidene)-6-oxa-2,13,19,22,25,28-hexazahexacyclo[29.3.1.0^{4,34}.0^{5,23}.0^{7,12}.0^{11,15}]pentatriaconta-1(34),3,7,9,11,14,31(35),32-octaen-30-yl]propylazanium |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| InChI | InChI | 1.06 | InChI=1S/C49H56N12O12/c50-12-4-7-26-22-10-11-28-29(19-54-32(28)14-22)42-41(61-44(66)33(16-38(52)64)56-43(65)30(51)13-23-18-55-39-27(23)6-3-9-37(39)73-42)48(70)59-36(21-63)46(68)60-40(26)47(69)58-35(20-62)45(67)57-34(49(71)72)15-24-17-53-31-8-2-1-5-25(24)31/h1-3,5-6,8-11,14,17-19,26,30,33-36,40-42,53-55,62-63H,4,7,12-13,15-16,20-21,50-51H2,(H2,52,64)(H,56,65)(H,57,67)(H,58,69)(H,59,70)(H,60,68)(H,61,66)(H,71,72)/p+1/t26-,30-,33-,34-,35-,36-,40-,41-,42+/m0/s1 |
| InChIKey | InChI | 1.06 | XINCMJVVCJHCMS-JXJNQVOLSA-O |
| SMILES_CANONICAL | CACTVS | 3.385 | N[C@H]1Cc2c[nH]c3c(O[C@H]4[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](CCC[NH3+])c5ccc6c([nH]cc46)c5)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc7c[nH]c8ccccc78)C(O)=O)cccc23 |
| SMILES | CACTVS | 3.385 | N[CH]1Cc2c[nH]c3c(O[CH]4[CH](NC(=O)[CH](CC(N)=O)NC1=O)C(=O)N[CH](CO)C(=O)N[CH]([CH](CCC[NH3+])c5ccc6c([nH]cc46)c5)C(=O)N[CH](CO)C(=O)N[CH](Cc7c[nH]c8ccccc78)C(O)=O)cccc23 |
| SMILES_CANONICAL | OpenEye OEToolkits | 2.0.7 | c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H]3C(c4ccc5c(c4)[nH]cc5C6[C@@H](C(=O)N[C@H](C(=O)N3)CO)NC(=O)[C@@H](NC(=O)[C@H](Cc7c[nH]c8c7cccc8O6)N)CC(=O)N)CCC[NH3+] |
| SMILES | OpenEye OEToolkits | 2.0.7 | c1ccc2c(c1)c(c[nH]2)CC(C(=O)O)NC(=O)C(CO)NC(=O)C3C(c4ccc5c(c4)[nH]cc5C6C(C(=O)NC(C(=O)N3)CO)NC(=O)C(NC(=O)C(Cc7c[nH]c8c7cccc8O6)N)CC(=O)N)CCC[NH3+] |
