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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB001025 |
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Identification |
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| Name: |
N-Acetylmuramoyl-Ala |
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| Description: | N-acetylmuramoyl-Ala is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. |
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Structure |
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| Synonyms: | - N-Acetyl-D-muramoyl-L-alanine
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Chemical Formula: |
C14H24N2O9 |
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| Average Molecular Weight: |
364.3484 |
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| Monoisotopic Molecular
Weight: |
364.148180376 |
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| InChI Key: |
ICMUIFDBEVJCQA-GQQBCVOHSA-N |
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| InChI: | InChI=1S/C14H24N2O9/c1-5(13(21)22)15-12(20)6(2)24-11-9(16-7(3)18)14(23)25-8(4-17)10(11)19/h5-6,8-11,14,17,19,23H,4H2,1-3H3,(H,15,20)(H,16,18)(H,21,22)/t5-,6-,8-,9-,10-,11-,14+/m1/s1 |
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| CAS
number: |
Not Available |
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| IUPAC Name: | (2R)-2-{[(2R)-2-{[(2S,3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid |
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Traditional IUPAC Name: |
N-acetylmuramoyl-ala |
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| SMILES: | [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(O)[C@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. |
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Kingdom |
Organic compounds |
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| Super Class | Organooxygen compounds |
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Class |
Carbohydrates and carbohydrate conjugates |
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| Sub Class | Aminosaccharides |
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Direct Parent |
N-acyl-alpha-hexosamines |
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| Alternative Parents |
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| Substituents |
- N-acyl-alpha-hexosamine
- N-acyl-aliphatic-alpha amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Glucosamine
- Amino sugar
- Alpha-amino acid or derivatives
- Oxane
- Monosaccharide
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid
- Carboxylic acid derivative
- Carboximidic acid derivative
- Carboximidic acid
- Hydrocarbon derivative
- Primary alcohol
- Organonitrogen compound
- Carbonyl group
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework |
Aliphatic heteromonocyclic compounds |
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| External Descriptors |
Not Available |
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Physical Properties |
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| State: |
Not Available |
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| Charge: | -2 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Cytoplasm |
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| Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
| Resource | Link |
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| CHEBI ID | Not Available | | HMDB ID | HMDB60494 | | Pubchem Compound ID | 5462248 | | Kegg ID | C02999 | | ChemSpider ID | 4575343 | | Wikipedia ID | Not Available | | BioCyc ID | Not Available |
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