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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 | PAMDB001694 |
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Identification |
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| Name: |
Tetrahydromonapterin |
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| Description: | Tetrahydromonapterin is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Tetrahydromonapterin is a major pterin in Pseudomonas aeruginosa and is hypothesized to be the cofactor for phenylalanine hydroxylase (PhhA) in Pseudomonas aeruginosa, but neither its biosynthetic origin nor its cofactor role has been clearly demonstrated. Collectively, these data establish that tetrahydromonapterin formation requires both FolX and FolM, that tetrahydromonapterin is the physiological cofactor for PhhA, and that tetrahydromonapterin can outrank folate as an end product of pterin biosynthesis. (PMID 19897652) |
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Structure |
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| Synonyms: | |
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Chemical Formula: |
C9H15N5O4 |
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| Average Molecular Weight: |
257.2465 |
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| Monoisotopic Molecular
Weight: |
257.112403993 |
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| InChI Key: |
XHIXPVCTDRNTTC-YQVKZWHSSA-N |
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| InChI: | InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)/t3?,4-,6-/m0/s1 |
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| CAS
number: |
Not Available |
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| IUPAC Name: | 2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one |
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Traditional IUPAC Name: |
2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one |
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| SMILES: | [H]OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[H] |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. |
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Kingdom |
Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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Class |
Pteridines and derivatives |
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| Sub Class | Pterins and derivatives |
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Direct Parent |
Biopterins and derivatives |
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| Alternative Parents |
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| Substituents |
- Biopterin
- Hydroxypyrimidine
- Secondary aliphatic/aromatic amine
- Sugar alcohol
- Pyrimidine
- Heteroaromatic compound
- 1,3-aminoalcohol
- Secondary alcohol
- Polyol
- 1,2-diol
- 1,2-aminoalcohol
- Azacycle
- Secondary amine
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework |
Aromatic heteropolycyclic compounds |
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| External Descriptors |
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Physical Properties |
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| State: |
Not Available |
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| Charge: | 0 |
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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: |
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Pribat, A., Blaby, I. K., Lara-Nunez, A., Gregory, J. F. 3rd, de Crecy-Lagard, V., Hanson, A. D. (2010). "FolX and FolM are essential for tetrahydromonapterin synthesis in Escherichia coli and Pseudomonas aeruginosa." J Bacteriol 192:475-482. Pubmed: 19897652
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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: |
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