Virginiamycin M1
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Grundinformationen
- CAS
21411-53-0- Standard-SMILES
CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1- InChIKey
DAIKHDNSXMZDCU-FQTGFAPKSA-N- Summenformel
- C28H35N3O7
- Durchschnittliche Molmasse
- 525,6 g/mol
- Monoisotopische Masse
- 525,24750046
Überblick
Pristinamycin IIA is a macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms including methicillin-resistant Staphylococcus aureus. It has a role as a Mycoplasma genitalium metabolite and an antibacterial drug. It is a secondary carboxamide, a tertiary carboxamide, a pyrroline, a lactam, a macrolide antibiotic, a macrolide, a secondary alcohol, a cyclic ketone, a member of 1,3-oxazoles and an enamide.
Namen und Bezeichner
- Bevorzugter Name
- Virginiamycin M1
- IUPAC
- (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
- Lokaler Name
- Virginiamycin M1
- Englischer Name
- VIRGINIAMYCIN M1
- Summenformel
- C28H35N3O7
- Molmasse
- 525.59
Namen und Synonyme
virginiamycin m1Streptogramin AMikamycin APristinamycin IIAVirginiamycin Factor M1VERNAMYCIN AStaphylomycin M1Antibiotic PA 114A121411-53-0Antibiotic pa 114a8W4UOL59AZPA-114A
Weitere Namen anzeigen
C11299PA 114AFactor MNSC 87432NSC 244426STAPHYLOMYCIN
NSC-87432NSC-244426RP-12536CHEBI:99978,9,14,15,24,25-Hexahydro-14-hydroxy-3-isopropyl-4,12-dimethyl-3H-21,18-nitrilo-1H,22H-pyrrolo(2,1-c)(1,8,4,19)dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetroneDTXSID30873800NSC87432Staphylomycin M
Datenbank-Bezeichner
- CAS
21411-53-0- PubChem CID
- 5459319
- DTXSID
DTXSID30873800- ChEMBL
CHEMBL1236670- ChEBI
CHEBI:9997
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,5
- Polarare Oberfläche (TPSA)
- 139 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 38
- Formalladung
- 0
- Komplexität
- 1.030
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Antibiotics
SolubilityPoorly soluble in water
Physikochemische Eigenschaften
- Schmelzpunkt
- 165 · 165-167℃
- Siedepunkt
- 825.2 · 825.2±65.0 °C(Predicted)
- Dichte
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 10 mg/mL · chloroform/methanol: soluble10mg/mL
- Aggregatzustand
- powder
- pka
- 13.18 · 13.18±0.70(Predicted)
- Farbe
- yellow to tan
- Stabilität
- Light Sensitive
- InChIKey
- DAIKHDNSXMZDCU-QHKJSJJMSA-N
- SMILES
- CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29419090
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Virginiamycin M1 is a macrocyclic lactone antibiotic that acts syngeristically with the structurally unrelated cyclic depsipeptides more commonly known as the virginiamycins B (ostreogrycin B or streptogramin B) and S to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Virginiamycin M1 has proven to be highly active against Gram positive bacteria, particularly methicillin-resistant S. aureus.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Anwendungen
VerwendenOstreogrycin A (virginiamycin M1, streptogramin A) is the major component of the virginamycin complex. In the 1950s this complex was independently discovered so many times that the literature became highly confusing. Ostreogrycin A is a macrocyclic lactone antibiotic that acts synergistically with the structurally unrelated cyclic depsipeptides, virginiamycin B (ostreogrycin B, streptogramin B) and virginiamycin S, to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Ostreogrycin A is highly active against Gram positive bacteria, particularly MRSA.
Ergänzende Hinweise
DefinitionChEBI: A macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms includ ng methicillin-resistant Staphylococcus aureus.
Zugehörige Reaktionen
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