Structure via PubChem · Public domain (PubChem)
ferrichrome
Sign in to saveFerrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.
Chemical data
- Formula
- C27H42FeN9O12
- Molecular weight
- 740.5 g/mol
- IUPAC name
- N-[3-[(2S,5S,8S)-5,8-bis[3-[acetyl(oxido)amino]propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-oxidoacetamide;iron(3+)
- SMILES
- CC(=O)N(CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)NCC(=O)NCC(=O)N1)CCCN(C(=O)C)[O-])CCCN(C(=O)C)[O-])[O-].[Fe+3]
- InChIKey
- GGUNGDGGXMHBMJ-OCIDDWSYSA-N
- Polar surface area
- 305 Ų
- H-bond donors
- 6
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
648 papers- Ferrichrome, a fungal-type siderophore, confers high ammonium tolerance to fission yeast.Scientific reports · 2022
- Probiotic-derived ferrichrome induces DDIT3-mediated antitumor effects in esophageal cancer cells.Heliyon · 2024
- Bacteria-derived ferrichrome inhibits tumor progression in sporadic colorectal neoplasms and colitis-associated cancer.Cancer cell international · 2021
- Elucidation of the ferrichrome siderophore biosynthetic pathway in albomycin-producing Streptomyces sp. ATCC 700974.The Journal of biological chemistry · 2023
- Probiotic‑derived ferrichrome inhibits the growth of refractory pancreatic cancer cells.International journal of oncology · 2020
via PubMed
Wikidata facts
- Subclass of
- siderophore
- Mass
- 740.23023
Show 4 more facts
- Commons category
- Ferrichrome
- chemical formula
- C₂₇H₄₂FeN₉O₁₂
- canonical SMILES
- CC(=O)N(CCCC1C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NCC(=O)N1)CCCN(C(=O)C)[O-])CCCN(C(=O)C)[O-])[O-].[Fe+3]
- different from
- ferrochrome
via Wikidata · CC0
~8 min read
Encyclopedic overview
6 sectionsContents
- Biological function
- Uptake
- Siderophore binding
- FhuA uptake mechanism
- See also
- References
Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.
Ferrichrome was first isolated in 1952, and has been found to be produced by fungi of the genera Aspergillus, Ustilago, and Penicillium. However, at the time there was no understanding regarding its involvement and contribution to iron transport. It was not until 1957 because of Joe Neilands' work, where he first noted that Ferrichrome was able to act as an iron transport agent.
Excerpted from Wikipedia’s “ferrichrome” article, available under the CC BY-SA 4.0 licence.