(16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo-1,2,8,14,15,17-hexahydrochromeno[2',3':6,7]naphtho[2,1-g]oxazolo[3,2-b]isoquinolin-3a(4H)-yl)methyl 3-methylbutanoate
Basic information
- CAS
122535-63-1- Standard SMILES
COc1cc2oc3c(c(=O)c2cc1OC)C(=O)c1c(ccc2cc4c(c(O)c12)C(=O)N1C(COC(=O)CC(C)C)(C4)OC(=O)C1(C)C)C3=O- InChIKey
CWPZIGIUHZNJEJ-UHFFFAOYSA-N- Molecular formula
- C36H31NO12
- Average molar mass
- 669.6 g/mol
- Monoisotopic mass
- 669.18462542
Overview
(16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo-1,2,8,14,15,17-hexahydrochromeno[2',3':6,7]naphtho[2,1-g]oxazolo[3,2-b]isoquinolin-3a(4H)-yl)methyl 3-methylbutanoate has been reported in Micromonospora citrea with data available.
Names & identifiers
- Preferred name
- (16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo-1,2,8,14,15,17-hexahydrochromeno[2',3':6,7]naphtho[2,1-g]oxazolo[3,2-b]isoquinolin-3a(4H)-yl)methyl 3-methylbutanoate
- IUPAC
- (3-hydroxy-23,24-dimethoxy-7,7-dimethyl-5,8,18,27,29-pentaoxo-9,20-dioxa-6-azaheptacyclo[15.12.0.02,14.04,12.06,10.019,28.021,26]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaen-10-yl)methyl 3-methylbutanoate
- English name
- citreamicin alpha
- Molecular formula
- C36H31NO12
- Molecular weight
- 669.63
Names & synonyms
(16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo-1,2,8,14,15,17-hexahydrochromeno[2',3':6,7]naphtho[2,1-g]oxazolo[3,2-b]isoquinolin-3a(4H)-yl)methyl 3-methylbutanoate(3-Hydroxy-23,24-dimethoxy-7,7-dimethyl-5,8,18,27,29-pentaoxo-9,20-dioxa-6-azaheptacyclo[15.12.0.02,14.04,12.06,10.019,28.021,26]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaen-10-yl)methyl 3-methylbutanoateSCHEMBL29399873DTXSID40924195(16-Hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo-1,2,8,14,15,17-hexahydro[1]benzopyrano[2',3':6,7]naphtho[2,1-g][1,3]oxazolo[3,2-b]isoquinolin-3a(4H)-yl)methyl 3-methylbutanoateButanoic acid, 3-methyl-, (1,2,8,14,15,17-hexahydro-16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo(1)benzopyrano(2',3':6,7)naphth(2,1-g)oxazolo(3,2-b)isoquinolin-3a(4H)-yl)methyl esterLL-E-19085αCitreamicin αLL-E19085alphacitreamicin alpha3-Methylbutanoic acid [(1,2,8,14,15,17-hexahydro-16-hydroxy-11,12-dimethoxy-1,1-dimethyl-2,8,14,15,17-pentaoxo[1]benzopyrano[2',3':6,7]naphth[2,1-g]oxazolo[3,2-b]isoquinolin)-3a(4H)-yl]methyl ester
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 172 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 7
- Heavy atoms
- 49
- Formal charge
- 0
- Complexity
- 1,520
Physicochemical properties
- Boiling point
- 886.598 · 886.598±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.531 · 1.531±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 6.125 · 6.125±0.60(predicted)
Chemistry & industry
Applications
DescriptionCitreamicin alpha is an antibacterial agent isolated from Micromonospora citrea.
UsesCitreamicin alpha (LL-E 19085-alpha) is an antibiotic whose in vitro antimicrobial activity against 429 clinical isolates of Gram-positive cocci has been tested by the agar dilution method. These microorganisms included 313 strains of Staphylococci and 116 strains of Streptococci. The in vitro activity of Citreamicin alpha was compared with that of ampicillin, amoxicillin, ceftriaxone, erythromycin, and vancomycin. For Staphylococci, the MIC values of Citreamicin alpha ranged from 0.12-4.0 μg/ml, and for Streptococcus pyogenes of the genus Streptococcus, it was 0.03-0.12 μg/ml. However, enterococci were relatively resistant, requiring 2.0 μg/ml of the agent to inhibit 64% of the 62 tested strains. The in vitro activity of this antibiotic was much better than that of ampicillin, amoxicillin, ceftriaxone, and erythromycin, but comparable or slightly inferior to that of vancomycin.
Related reactions
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Compound notes
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