PRD_000728
Summary
| Name: | Synthetic PYOVERDINE Fe Complex |
| Formula: | C56 H81 Fe N17 O24 |
| Fomular weight: | 1432.187 |
| Component type: | peptide-like |
| Polymer sequences: | DSN, LYS, GLY, FHO, SER, DSN, GLY, ORN, FH7, SER |
| Non-polymer components: | |
| BIRD class: | Metal Transport |
| Represented as: | polymer |
| Compound Details: | PYOVERDINES ARE A GROUP OF STRUCTURALLY RELATED SIDEROPHORES PRODUCED BY FLUORESCENT PSEUDOMONAS SPECIES. PYOVERDINE IS NECESSARY FOR INFECTION IN SEVERAL DIFFERENT DISEASE MODELS. THE OCCURRENCE OF PYOVERDINE-DEFECTIVE STRAINS IN CHRONIC INFECTIONS OF PATIENTS WITH CYSTIC FIBROSIS AND THE EXTREMELY HIGH SEQUENCE DIVERSITY OF GENES INVOLVED IN PYOVERDINE SYNTHESIS AND UPTAKE INDICATE THAT PYOVERDINE PRODUCTION IS SUBJECT TO HIGH EVOLUTIONARY PRESSURE. PYOVERDINE-DEPENDENT IRON TRANSPORT IS ALSO CRUCIAL FOR BIOFILM DEVELOPMENT, FURTHER EXPANDING THE IMPORTANCE OF THESE SIDEROPHORES IN PSEUDOMONAS BIOLOGY. |
| Description: | IN IRON-DEFICIENT CONDITIONS, PSEUDOMONAS AERUGINOSA SECRETES A MAJOR FLUORESCENT SIDEROPHORE NAMED PYOVERDIN (PVD), WHICH AFTER CHELATING IRON(III) IS TRANSPORTED BACK INTO THE CELL VIA ITS OUTER MEMBRANE RECEPTOR FPVA. FPVA IS A TONB-DEPENDENT TRANSPORT PROTEIN AND HAS THE ABILITY TO BIND PVD IN ITS APO- OR IRON-LOADED FORM. |
| Families: | FAM_000420 |
| Program | Version | Name |
| ACDLabs | 12.01 | [N-{[(1R)-5-[(3-carboxypropanoyl)amino]-8,9-di(hydroxy-kappaO)-1,2,3,4-tetrahydropyrimido[1,2-a]quinolin-11-ium-1-yl]carbonyl}-D-seryl-6-ammonio-L-norleucylglycyl-N~5~-(formyl-kappaO)-N~5~-(hydroxy-kappaO)-L-ornithyl-L-seryl-D-seryl-N-[(3S,6S,9R)-6-{3-[(formyl-kappaO)(hydroxy-kappaO)amino]propyl}-3-(hydroxymethyl)-2,5,8-trioxo-1,4,7-triazacyclododecan-9-yl]glycinamidato(4-)]iron(5+) |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=C(O)CCC(=O)Nc3cc9c2cc8o[Fe+3]615(ocn(o1)CCCC7C(=O)NC(C(=O)NCCCC(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C4[n+]2c3NCC4)CO)CCCC[NH3+])CCCn(o5)co6)CO)CO)C(=O)N7)CO)oc8c9 |
| InChI | InChI | 1.03 | InChI=1S/C56H81N17O24.Fe/c57-13-2-1-6-30(65-54(93)38(26-77)70-56(95)39-12-15-58-47-34(64-43(82)10-11-46(85)86)18-29-19-41(80)42(81)20-40(29)73(39)47)48(87)60-21-44(83)63-32(8-4-16-71(96)27-78)52(91)69-37(25-76)55(94)68-36(24-75)50(89)61-22-45(84)62-31-7-3-14-59-49(88)35(23-74)67-53(92)33(66-51(31)90)9-5-17-72(97)28-79;/h18-20,27-28,30-33,35-39,74-77H,1-17,21-26,57H2,(H15,58,59,60,61,62,63,64,65,66,67,68,69,70,80,81,82,83,84,85,86,87,88,89,90,91,92,93,94,95);/q-2;+7 |
| InChIKey | InChI | 1.03 | JWTJSISARVZWST-UHFFFAOYSA-N |
| SMILES_CANONICAL | CACTVS | 3.370 | [NH3+]CCCC[C@@H]1NC(=O)[C@@H](CO)NC(=O)[C@@H]2CCNc3c(NC(=O)CCC(O)=O)cc4cc5O[Fe+3]6|78(|O=C[N@@](CCC[C@H](NC(=O)CNC1=O)C(=O)N[C@@H](CO)C(=O)N[C@H](CO)C(=O)NCC(=O)N[C@H]9CCCNC(=O)[C@H](CO)NC(=O)[C@@H](CCC[N@](O6)C=O|7)NC9=O)O8)Oc5cc4[n+]23 |
| SMILES | CACTVS | 3.370 | [NH3+]CCCC[CH]1NC(=O)[CH](CO)NC(=O)[CH]2CCNc3c(NC(=O)CCC(O)=O)cc4cc5O[Fe+3]6|78(|O=C[N](CCC[CH](NC(=O)CNC1=O)C(=O)N[CH](CO)C(=O)N[CH](CO)C(=O)NCC(=O)N[CH]9CCCNC(=O)[CH](CO)NC(=O)[CH](CCC[N](O6)C=O|7)NC9=O)O8)Oc5cc4[n+]23 |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | c1c2cc3c4cc2[n+]5c(c1NC(=O)CCC(=O)O)NCC[C@H]5C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H]6CCCN7C=O[Fe+3]8(O3)(O4)(O7)O=CN(O8)CCC[C@@H]9C(=O)N[C@H](C(=O)NCCC[C@@H](C(=O)N9)NC(=O)CNC(=O)[C@H](NC(=O)[C@@H](NC6=O)CO)CO)CO)CCCC[NH3+])CO |
| SMILES | OpenEye OEToolkits | 1.7.6 | c1c2cc3c4cc2[n+]5c(c1NC(=O)CCC(=O)O)NCCC5C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC6CCCN7C=O[Fe+3]8(O3)(O4)(O7)O=CN(O8)CCCC9C(=O)NC(C(=O)NCCCC(C(=O)N9)NC(=O)CNC(=O)C(NC(=O)C(NC6=O)CO)CO)CO)CCCC[NH3+])CO |
