BIRD-PRD_000723: PYOVERDIN C-E Fe Complex

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000723
• Status: Status: REF ONLY
• Name: PYOVERDIN C-E Fe Complex

BIRD information

• Type: Polypeptide / Metal Transport

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.
• 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.

• Downloads: Molecular definition / Chemical definition / Family definition

Annotation

• Function: iron binding / Info source: PubMed: 19504741

Source

• PSEUDOMONAS AERUGINOSA, STRAIN PAO1, Norine: NOR00190

External info

• Norine: NOR00190

Family

PYOVERDINE

PYOVERDIN C-E CHROMOPHORE / PYOVERDIN C-E Fe Complex / PYOVERDIN 18-1 Fe Complex / PYOVERDIN R Fe Complex / BIRD: PRD_000726 / PYOVERDIN G173 Fe Complex / Synthetic PYOVERDINE Fe Complex

Chemical information

Composition

Formula: C₅₅H₈₂FeN₁₇O₂₂ / Formula weight: 1389.185

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(O)CCC(=O)Nc3cc9c2cc8o[Fe+3]615(ocn(o1)CCCC7C(=O)NC(C(=O)NC(C(=O)[NH2+]CCCCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C4[n+]2c3NCC4)CO)CCCNC(=[NH2+])\N)CO)CCCn(o5)co6)C(=O)N7)C(O)C)C(O)C)oc8c9
• CACTVS 3.370: C[CH](O)[CH]1NC(=O)[CH]2CCC[N]3O[Fe+3]456(|O=C[N](CCC[CH](NC(=O)[CH](CO)NC(=O)[CH](CCCNC(N)=[NH2+])NC(=O)[CH](CO)NC(=O)[CH]7CCNc8c(NC(=O)CCC(O)=O)cc9cc(O4)c(O5)cc9[n+]78)C(=O)N[CH](CCCC[NH2+]C(=O)[CH](NC1=O)[CH](C)O)C(=O)N2)O6)|O=C3
• OpenEye OEToolkits 1.7.6: CC(C1C(=O)[NH2+]CCCCC2C(=O)NC(CCCN3C=O[Fe+3]456(O3)O=CN(O4)CCCC(C(=O)N2)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C7CCNc8[n+]7c9cc(c(cc9cc8NC(=O)CCC(=O)O)O5)O6)CO)CCCNC(=[NH2+])N)CO)C(=O)NC(C(=O)N1)C(C)O)O

SMILES CANONICAL

• CACTVS 3.370: C[C@@H](O)[C@@H]1NC(=O)[C@@H]2CCC[N@@]3O[Fe+3]456(|O=C[N@](CCC[C@H](NC(=O)[C@@H](CO)NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H](CO)NC(=O)[C@@H]7CCNc8c(NC(=O)CCC(O)=O)cc9cc(O4)c(O5)cc9[n+]78)C(=O)N[C@@H](CCCC[NH2+]C(=O)[C@@H](NC1=O)[C@@H](C)O)C(=O)N2)O6)|O=C3
• OpenEye OEToolkits 1.7.6: C[C@H]([C@H]1C(=O)[NH2+]CCCC[C@H]2C(=O)N[C@@H](CCCN3C=O[Fe+3]456(O3)O=CN(O4)CCC[C@@H](C(=O)N2)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H]7CCNc8[n+]7c9cc(c(cc9cc8NC(=O)CCC(=O)O)O5)O6)CO)CCCNC(=[NH2+])N)CO)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)O

InChI

• InChI 1.03: InChI=1S/C55H81N17O22.Fe/c1-27(77)43-53(91)59-15-4-3-8-30(46(84)63-33(11-7-19-71(94)26-76)49(87)68-44(28(2)78)54(92)69-43)62-47(85)32(10-6-18-70(93)25-75)65-50(88)35(23-73)66-48(86)31(9-5-16-60-55(56)57)64-51(89)36(24-74)67-52(90)37-14-17-58-45-34(61-41(81)12-13-42(82)83)20-29-21-39(79)40(80)22-38(29)72(37)45;/h20-22,25-28,30-33,35-37,43-44,73-74,77-78H,3-19,23-24H2,1-2H3,(H17,56,57,58,59,60,61,62,63,64,65,66,67,68,69,79,80,81,82,83,84,85,86,87,88,89,90,91,92);/q-2;+7/p+1

InChIKey

• InChI 1.03: REEJEWYDVJJOLS-UHFFFAOYSA-O

SYSTEMATIC 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-N~5~-[amino(iminio)methyl]-L-ornithyl-D-seryl-N~5~-formyl-kappaO-N-{(3R,6S,9S,12R)-9-{3-[(formyl-kappaO)(hydroxy-kappaO)amino]propyl}-6-[(1R)-1-hydroxyethyl]-3-[(1S)-1-hydroxyethyl]-2,5,8,11-tetraoxo-4,7,10-triaza-1-azoniacyclohexadecan-12-yl}-N~5~-hydroxy-kappaO-L-ornithinamidato(4-)]iron(6+) #

PDB entries

Showing all 6 items

PDB-2iah:
Crystal structure of the ferripyoverdine receptor of the outer membrane of Pseudomonas aeruginosa bound to ferripyoverdine.

PDB-2iah:
Crystal structure of the ferripyoverdine receptor of the outer membrane of Pseudomonas aeruginosa bound to ferripyoverdine.

PDB-2iah:
Crystal structure of the ferripyoverdine receptor of the outer membrane of Pseudomonas aeruginosa bound to ferripyoverdine.

PDB-2w16:
Structures of FpvA bound to heterologous pyoverdines

PDB-2w16:
Structures of FpvA bound to heterologous pyoverdines

PDB-2w16:
Structures of FpvA bound to heterologous pyoverdines