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Novobiocin

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Identification
Molecular formula
C31H36N2O11
CAS number
1476-53-5
IUPAC name
[(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
State
State

Novobiocin is typically in a solid state at room temperature, usually as a crystalline powder.

Melting point (Celsius)
173.90
Melting point (Kelvin)
447.10
Boiling point (Celsius)
273.30
Boiling point (Kelvin)
546.50
General information
Molecular weight
613.63g/mol
Molar mass
613.6320g/mol
Density
0.9203g/cm3
Appearence

Novobiocin appears as a white to off-white crystalline powder. It does not have a distinct odor. It exhibits slight solubility in water and better solubility in alcohol and other organic solvents.

Comment on solubility

Solubility Analysis

The compound [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate exhibits unique solubility characteristics that are pertinent to its use in various applications. Understanding the solubility of this complex molecular structure can significantly impact its biological activity and effectiveness in pharmacological contexts.

Key Solubility Considerations:

  • Polarity: The presence of numerous functional groups, including amino and methoxy, can enhance polarity, potentially leading to increased solubility in polar solvents.
  • Hydrophobic Regions: The tetracyclic framework contributes to hydrophobic characteristics, which may limit solubility in highly polar solvents.
  • Solvent Interactions: Solubility may vary dramatically in different solvents, highlighting the importance of testing in systems like water, alcohols, or organic solvents.

As a general observation, compounds like this may show the following solubility behaviors:

  1. Moderate to high solubility in polar aprotic solvents due to enhanced intermolecular interactions.
  2. Lower solubility in nonpolar solvents, stemming from the hydrophobic nature of the core structure.
  3. pH Dependence: The solubility could also fluctuate based on the pH of the solution, as protonation states of the amino group can affect solubility.

In essence, the solubility characteristics of this compound can be regarded as a balance between its polar functional groups and its hydrophobic structure. Therefore, thorough empirical investigations are essential to elucidate its solubility profile in various environments.

Interesting facts

Interesting Facts about (4S,6S,7R,8S)-11-Amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

This complex compound belongs to a class of chemical entities known for their diverse biological activities. Here are some intriguing points to note:

  • Structural Complexity: The structural design of this compound showcases a unique tetracyclic framework, contributing to its potential pharmaceutical properties. The presence of multiple functional groups, including amino and methoxy, highlights its role in various chemical reactions.
  • Biological Significance: Compounds like this one are often investigated for their biological activities. They may exhibit antibacterial or antifungal properties, making them valuable in medicinal chemistry.
  • Mechanism of Action: Although the exact mechanism of action may vary, the presence of the carbamate moiety is known to interact with various biological pathways through enzyme inhibition, providing a potential target for drug development.
  • Synthetic Challenges: The synthesis of such complex molecules is often a challenge. Chemists employ a range of advanced techniques, including asymmetric synthesis and protective group strategies, to construct these compounds efficiently.
  • Research Potential: Given its unique structure, this compound could serve as a scaffold for the development of new therapeutic agents. Easier modifications could lead to discovering derivatives with improved efficacy and selectivity.

As scientists continue to explore the vast potential of chemical compounds like (4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate, the future of medicinal chemistry holds exciting prospects!

Synonyms
Porfiromycin
801-52-5
N-Methylmitomycin C
Methylmitomycin
Methyl mitomycin C
Porfiromicina
Porfiromycine
Porfiromycinum
ENT-50825
NSC-56410
Nsc 56410
Porfiromycine [INN-French]
Porfiromycinum [INN-Latin]
Porfiromicina [INN-Spanish]
Porphyromycin
U-14743
Porfiromycin [USAN:INN:BAN]
H1WK901OA6
AI3-50825
Mitomycin C, N-methyl-
PORFIROMYCIN [MI]
PORFIROMYCIN [INN]
PORFIROMYCIN [USAN]
U-14,743
PORFIROMYCIN [MART.]
PORFIROMYCIN [WHO-DD]
6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione carbamate (ester)
N-METHYLMITOMYCIN C [MI]
DTXSID901024646
[(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
Azirino(2',3':3,4)pyrrolo(1,2-a)-indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-
Methylmitomycin C
Porfiromycine (INN-French)
Porfiromycinum (INN-Latin)
Porfiromicina (INN-Spanish)
PORFIROMYCIN (MART.)
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester)
Promycin
NSC56410
(1AS-(1A.ALPHA.,8.BETA.,8A.ALPHA.,8B.ALPHA.))-6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-1,5-DIMETHYLAZIRINO(2';,3';:3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE
Methyl Mitomycin
((4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo(7.4.0.02,7.04,6)trideca-1(9),11-dien-8-yl)methyl carbamate
(1aS-(1a alpha,8beta,8a alpha,8b alpha))-6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione
[1aS-(1a alpha,8beta,8a alpha,8b alpha)]-6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
Mitomycin, methyl-
MITOMYCIN, METHYL
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-, (1aS-(1aalpha,8beta,8aalpha,8balpha))-
DTXCID601508835
(1AS-(1AALPHA,8BETA,8AALPHA,8BALPHA))-6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-1,5-DIMETHYLAZIRINO(2';,3';:3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE
Azirino(2',3':3,4)pyrrolo(1, 2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a, 8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester)
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester) (8CI)
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1a-alpha,8beta, 8a-alpha,8b-alpha))-
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1aalpha,8beta, 8aalpha,8balpha))-
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1aalpha,8beta,8aalpha,8balpha))-
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1aalpha,8beta,8aalpha,8balpha))-(9CI)
Azirino[2',3':3,4]pyrrolo[1, 2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a, 8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester) (8CI)
Azirino[2',3':3,4]pyrrolo[1, 2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a, 8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester)(8CI)
Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,[1aR-(1a-alpha,8beta, 8a-alpha,8b-alpha)]-(9CI)
Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-,[1aR-(1a.alpha.,8.beta., 8a.alpha.,8b.alpha.)]-(9CI)
Regamycin
((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate
UNII-H1WK901OA6
Porfiromycin (USAN/INN)
SCHEMBL5046
CHEMBL521078
CHEBI:208611
ENT 50825; Methyl mitomycin C
AP27106
DB06478
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- methoxy-1,5-dimethyl-, carbamate (ester)
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1aalpha,8beta,8aalpha,8balpha))-
DA-66827
HY-13730
CS-0007759
NS00073289
D05572
(amino-methoxy-dimethyl-dioxo-[?]yl)methyl carbamate
Q27279527
6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, carbamate ester
Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-, (1aS,8S,8aR,8bS)-