Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:36 UTC |
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Updated at | 2022-03-10 22:17:40 UTC |
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NP-MRD ID | NP0044320 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-Methyltetrahydropteroyltri-L-glutamic acid |
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Description | 5-Methyltetrahydropteroyltri-L-glutamic acid, also known as 5-methyl-5,6,7,8-tetrahydropteroyl tri-gamma-L-glutamate or 5-methyltetrahydrofolate triglutamate, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof). It is also involved in several pathways as a product of enzymatic oxidation such as in the pathways folate polyglutamylation I and carbon tetrachloride degradation II. 5-Methyltetrahydropteroyltri-L-glutamic acid (CAS: 13061-55-7) Is formed during the reaction between the carbonyl group of 5-methyltetrahydropteroate and the amine group on one end of three replicates of glutamate. 5-Methyltetrahydropteroyltri-L-glutamic acid is a strong basic compound (based on its pKa). In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. 5-Methyltetrahydropteroyltri-L-glutamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 5-Methyltetrahydropteroyltri-L-glutamic acid has been detected, but not quantified in, several different foods, such as chives, flaxseeds, sweet marjorams, butternut squash, and mandarin orange (clementine, tangerine). This could make 5-methyltetrahydropteroyltri-L-glutamic acid a potential biomarker for the consumption of these foods. It is involved in several pathways as a product of enzymatic reduction such as in tetrahydrofolate biosynthesis II and methionine biosynthesis I, II, and III. 5-Methyltetrahydropteroyltri-L-glutamic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2 InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/t16-,17-,18-,19-/m0/s1 |
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Synonyms | Value | Source |
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5-Methyltetrahydropteroyltri-L-glutamate | ChEBI | 5-Methyl-5,6,7,8-tetrahydropteroyl tri-gamma-L-glutamate | HMDB | 5-Methyl-5,6,7,8-tetrahydropteroyl tri-γ-L-glutamate | HMDB | 5-Methyltetrahydrofolate triglutamate | HMDB | 5-Methyltetrahydropteroyl-gamma-glutamyl-gamma-glutamylglutamic acid | HMDB | 5-Methyltetrahydropteroyl-γ-glutamyl-γ-glutamylglutamic acid | HMDB | 5-Methyltetrahydropteroyltri-L-glutamic acid | HMDB, Generator |
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Chemical Formula | C30H39N9O12 |
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Average Mass | 717.6838 Da |
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Monoisotopic Mass | 717.27182 Da |
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IUPAC Name | (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid |
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Traditional Name | (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid |
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CAS Registry Number | 133321-34-3 |
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SMILES | CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2 |
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InChI Identifier | InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/t16-,17-,18-,19-/m0/s1 |
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InChI Key | HVRNKDVLFAVCJF-VJANTYMQSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof). |
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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 | Tetrahydrofolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Tetrahydrofolic acid or derivatives
- Alpha-oligopeptide
- Gamma-glutamyl alpha-amino acid
- Glutamic acid or derivatives
- Glutamine or derivatives
- Tetracarboxylic acid or derivatives
- N-acyl-l-alpha-amino acid
- Hippuric acid or derivatives
- Hippuric acid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Aminobenzamide
- Alpha-amino acid or derivatives
- Aminobenzoic acid or derivatives
- Benzoic acid or derivatives
- Benzamide
- Tertiary aliphatic/aromatic amine
- Benzoyl
- Phenylalkylamine
- Aniline or substituted anilines
- Dialkylarylamine
- Aminopyrimidine
- Pyrimidone
- Secondary aliphatic/aromatic amine
- Pyrimidine
- Monocyclic benzene moiety
- Benzenoid
- N-acyl-amine
- Fatty acyl
- Fatty amide
- Vinylogous amide
- Heteroaromatic compound
- Amino acid or derivatives
- Tertiary amine
- Secondary carboxylic acid amide
- Amino acid
- Carboxamide group
- Secondary amine
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Primary amine
- Amine
- Organic oxygen compound
- 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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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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