Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-23 16:12:27 UTC |
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Update Date | 2021-09-14 15:30:24 UTC |
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HMDB ID | HMDB0006563 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hexaglutamyl folate |
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Description | Hexaglutamyl folate is a naturally occurring form of folic acid. The bioavailability of dietary folate may be hampered by the need of the glutamate moieties to be deconjugated before absorption. Folate deficiency in humans leads to anemia, neural tube defects and, possibly, chronic diseases such as cardiovascular disease, colon cancer, and neurocognitive dysfunction. Folate status is ascertained not only by the intake of folate but also by its bioavailability. Bioavailability is defined as the proportion of ingested folate that is absorbed and available for metabolic processes and storage. In humans, the bioavailability of folate from the diet is assumed to be {approx}50%, whereas the bioavailability of synthetic folic acid used in supplements and as a food fortificant is estimated to range from 76% to 97%. (PMID: 17093166 ). Patients with pernicious anemia in relapse and postgastrectomy macrocytic anemia cannot readily utilize for hematopoiesis a naturally occurring conjugate of pteroylglutamic acid although they respond promptly to administration of the free vitamin. This effect varies in different patients. Inability to utilize the conjugated vitamin appears to depend at least in part upon a conjugase-inhibiting substance present in natural sources of conjugate. (PMID: 1082804 ). |
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Structure | N[C@@H](CCC(=O)OC(=O)[C@](N(C(=O)CC[C@H](N)C(O)=O)C(=O)C1=CC=C(NCC2=CN=C3NC(N)=NC(=O)C3=N2)C=C1)(C(=O)CC[C@H](N)C(O)=O)C(CC(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)CC[C@H](N)C(O)=O)C(O)=O InChI=1S/C44H54N12O21/c45-21(36(66)67)5-10-26(57)43(15-30(61)62,27(58)11-6-22(46)37(68)69)44(28(59)12-7-23(47)38(70)71,41(76)77-31(63)14-9-25(49)40(74)75)56(29(60)13-8-24(48)39(72)73)35(65)18-1-3-19(4-2-18)51-16-20-17-52-33-32(53-20)34(64)55-42(50)54-33/h1-4,17,21-25,51H,5-16,45-49H2,(H,61,62)(H,66,67)(H,68,69)(H,70,71)(H,72,73)(H,74,75)(H3,50,52,54,55,64)/t21-,22-,23-,24-,25-,44+/m0/s1 |
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Synonyms | Value | Source |
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Hexaglutamyl folic acid | Generator | Hexaglutamate folate | HMDB | N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-glutamic acid | HMDB | N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acid | HMDB | N-[N-[N-[N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-glutamic acid | HMDB | N-[N-[N-[N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-glutamic acid | HMDB | Pteglu6 | HMDB | Pteroyl-g-hexaglutamate | HMDB | Pteroyl-gamma-hexaglutamate | HMDB | Pteroylhexaglutamic acid | HMDB | (2S,7R,11S)-2,11-Diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{n-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioate | Generator, HMDB |
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Chemical Formula | C44H54N12O21 |
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Average Molecular Weight | 1086.9674 |
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Monoisotopic Molecular Weight | 1086.35264685 |
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IUPAC Name | (2S,7R,11S)-2,11-diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioic acid |
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Traditional Name | (2S,7R,11S)-2,11-diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioic acid |
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CAS Registry Number | 35409-55-3 |
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SMILES | N[C@@H](CCC(=O)OC(=O)[C@](N(C(=O)CC[C@H](N)C(O)=O)C(=O)C1=CC=C(NCC2=CN=C3NC(N)=NC(=O)C3=N2)C=C1)(C(=O)CC[C@H](N)C(O)=O)C(CC(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)CC[C@H](N)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C44H54N12O21/c45-21(36(66)67)5-10-26(57)43(15-30(61)62,27(58)11-6-22(46)37(68)69)44(28(59)12-7-23(47)38(70)71,41(76)77-31(63)14-9-25(49)40(74)75)56(29(60)13-8-24(48)39(72)73)35(65)18-1-3-19(4-2-18)51-16-20-17-52-33-32(53-20)34(64)55-42(50)54-33/h1-4,17,21-25,51H,5-16,45-49H2,(H,61,62)(H,66,67)(H,68,69)(H,70,71)(H,72,73)(H,74,75)(H3,50,52,54,55,64)/t21-,22-,23-,24-,25-,44+/m0/s1 |
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InChI Key | FWAQAOUHULVCBP-HCVVFSGQSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Glutamine and derivatives |
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Alternative Parents | |
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Substituents | - Glutamine or derivatives
- Glutamic acid or derivatives
- Hippuric acid or derivatives
- Pterin
- Alpha-amino acid
- Aminobenzamide
- Aminobenzoic acid or derivatives
- Pteridine
- L-alpha-amino acid
- Benzoic acid or derivatives
- Benzoyl
- Phenylalkylamine
- Aniline or substituted anilines
- Gamma-keto acid
- Aminopyrimidine
- Aralkylamine
- Beta-keto acid
- Amino fatty acid
- Pyrimidone
- Secondary aliphatic/aromatic amine
- Gamma-aminoketone
- Pyrimidine
- Pyrazine
- Benzenoid
- Fatty acyl
- Monocyclic benzene moiety
- Keto acid
- N-acyl-amine
- Carboxylic acid imide, n-substituted
- Heteroaromatic compound
- Carboxylic acid anhydride
- Carboxylic acid imide
- Dicarboximide
- Vinylogous amide
- Ketone
- Amino acid
- Secondary amine
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organic oxide
- Primary aliphatic amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 10V, Positive-QTOF | splash10-0g4m-9100000003-15476a59d2389d71c70b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 20V, Positive-QTOF | splash10-000t-5300000019-6661c8b1823b69eb1e01 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 40V, Positive-QTOF | splash10-01ta-8830000019-35fa3750a0cf421648ed | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 10V, Negative-QTOF | splash10-00or-9600000014-c457633361b67fb7f98c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 20V, Negative-QTOF | splash10-069c-8300000039-89e8ab9fb8aab17abe41 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 40V, Negative-QTOF | splash10-004i-5600001529-fcfb845bf09065280726 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 10V, Positive-QTOF | splash10-00ri-9000001000-c26a4c955d3cb316874f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 20V, Positive-QTOF | splash10-01xt-8000000009-f76fae5536125ad046da | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 40V, Positive-QTOF | splash10-002b-5413000009-ad2947564427152d302a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 10V, Negative-QTOF | splash10-000i-3000000009-4236dc77cfea70e2a3d5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 20V, Negative-QTOF | splash10-044l-9200100007-cc10ed0f30c954556c9b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexaglutamyl folate 40V, Negative-QTOF | splash10-0006-6090201012-0ce0a1c6ecafd105e22b | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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