Platensimycin
Basic information
- CAS
835876-32-9- Standard SMILES
C[C@]12C[C@@]34C=CC(=O)[C@@](C)(CCC(=O)Nc5c(O)ccc(C(=O)O)c5O)[C@@H]3[C@H](C[C@@H]1C4)O2- InChIKey
CSOMAHTTWTVBFL-OFBLZTNGSA-N- Molecular formula
- C24H27NO7
- Average molar mass
- 441.5 g/mol
- Monoisotopic mass
- 441.1787522
Overview
Platensimycin is a monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase. It has a role as an antimicrobial agent, an antibacterial agent, an EC 2.3.1.85 (fatty acid synthase) inhibitor and a bacterial metabolite. It is a dihydroxybenzoic acid, a monocarboxylic acid amide, a polycyclic cage, a cyclic ether, a cyclic ketone and an aromatic amide. It is a conjugate acid of a platensimycin(1-).
Names & identifiers
- Preferred name
- Platensimycin
- IUPAC
- 3-[3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.17,10.01,6]tridec-2-en-5-yl]propanoylamino]-2,4-dihydroxybenzoic acid
- English name
- PlatensiMycin
- Molecular formula
- C24H27NO7
- Molecular weight
- 441.474
Names & synonyms
PLATENSIMYCIN835876-32-9(-)-PlatensimycinQ3DQ78KOFY3-[3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.17,10.01,6]tridec-2-en-5-yl]propanoylamino]-2,4-dihydroxybenzoic acidCHEBI:68236DTXSID80894888Benzoic acid, 3-((3-((1S,3S,4S,5aS,9S,9aR)-1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2-benzoxepin-9-yl)-1-oxopropyl)amino)-2,4-dihydroxy-3-((3-((1S,3S,4S,5AS,9S,9AR)-1,4,5,8,9,9A-HEXAHYDRO-3,9-DIMETHYL-8-OXO-3H-1,4:3,5A-DIMETHANO-2-BENZOXEPIN-9-YL)-1-OXOPROPYL)AMINO)-2,4-DIHYDROXYBENZOIC ACID3-(3-((1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo(7.2.1.17,10.01,6)tridec-2-en-5-yl)propanoylamino)-2,4-dihydroxybenzoic acidRefChem:174784DTXCID201324447
Show more names
laminomycinPlatensimycin, Streptomyces sp.Platensimycin, Streptomyces sp. - CAS 835876-32-9 - CalbiochemBenzoic acid, 3-[[3-[(1S,3S,4S,5aS,9S,9aR)-1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2-benzoxepin-9-yl]-1-oxopropyl]amino]-2,4-dihydroxy-
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 133 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 888
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 220 · 220-222 °C(Solv: nitromethane (75-52-5))
- Boiling point
- 683.1 · 683.1±55.0 °C(Predicted)
- Density
- 1.47 · 1.47±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/mL, · DMSO: soluble1mg/mL, clear, colorless
- form
- Tan solid
- pka
- 2.14 · 2.14±0.13(Predicted)
- color
- white to beige
- InChIKey
- CSOMAHTTWTVBFL-OFBLZTNGSA-N
- FDA UNII
- 3 DQ78KOFY · Q3DQ78KOFY
- UNSPSC Code
- 12352200 · 12352200
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Compounds that interfere with FATTY ACID SYNTHASE resulting in a reduction of FATTY ACIDS. This is a target mechanism in humans of some ANTINEOPLASTIC AGENTS and ANTI-OBESITY AGENTS and of some ANTI-INFECTIVE AGENTS which interfere with CELL WALL and CELL MEMBRANE formation.
Applications
UsesPlatensimycin is a novel, broad spectrum, Gram-positive antibiotic produced by strains of Streptomyces platensis. Its discovery was heralded by high profile publication and commentary in the scientific and lay press. Platensimycin was discovered by a target-based, whole-cell screening strategy using an antisense differential sensitivity assay, based on the inhibition of fatty acid synthesis. Platensimycin inhibits bacterial growth by selectively inhibiting the elongation enzyme, b-ketoacyl acyl carrier protein synthase (FabF) of the fatty acid synthesis pathway.
UsesPlatensimycin is a broad spectrum gram-positive antibiotic.
Additional notes
DefinitionChEBI: A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis a d exhibits inhibitory activity against fatty acid synthase.
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