| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-17 18:59:13 UTC |
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| Updated at | 2020-11-18 16:39:11 UTC |
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| CannabisDB ID | CDB005002 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound 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-γ-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 | |
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| Synonyms | | Value | Source |
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| 5-Methyltetrahydropteroyltri-L-glutamate | ChEBI | | 5-Methyltetrahydropteroyltri-L-glutamic acid | HMDB, Generator | | 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 |
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| Chemical Formula | C30H39N9O12 |
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| Average Molecular Weight | 717.68 |
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| Monoisotopic Molecular Weight | 717.2718 |
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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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| 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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| Ontology |
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| Disposition | Route of exposure: Source: |
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| Physical Properties |
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| State | Solid |
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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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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Methyltetrahydropteroyltri-L-glutamic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0732118900-53d55fe9c0863d97f51f | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0932104100-d16b89e4058f4ac3aa4c | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-1921101000-70b11d23c3858386d9c9 | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00r2-0000009200-85df402e63838ca104ff | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fi1-0110019000-44613760172916ef7e66 | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004m-5931213000-75cc50202a2eca9054cb | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ikc-0429311800-370ce9231396acda8d92 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01u3-1625490000-4b2f69d8a822fdbfcca9 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02cu-1905000000-a42458750a4d98ede330 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0010009100-0dc6b367fdbdca7547fc | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zir-0330119000-1542d290911c87efd051 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ufr-1913110000-8e9ec4663cc7affb6895 | 2021-09-25 | View Spectrum |
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