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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 16:12:27 UTC
Update Date2019-01-11 19:19:25 UTC
HMDB IDHMDB0006563
Secondary Accession Numbers
  • HMDB06563
Metabolite Identification
Common NameHexaglutamyl folate
DescriptionHexaglutamyl 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 ).
Structure
Data?1547234365
Synonyms
ValueSource
Hexaglutamate folateHMDB
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 acidHMDB
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 acidHMDB
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 acidHMDB
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 acidHMDB
Pteglu6HMDB
Pteroyl-g-hexaglutamateHMDB
Pteroyl-gamma-hexaglutamateHMDB
Pteroylhexaglutamic acidHMDB
Chemical FormulaC44H54N12O21
Average Molecular Weight1086.9674
Monoisotopic Molecular Weight1086.35264685
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
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
CAS Registry Number35409-55-3
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
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
InChI KeyFWAQAOUHULVCBP-HCVVFSGQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glutamine and derivatives. These 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP-2.6ALOGPS
logP-8.8ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.1ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area591.15 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity252.39 m³·mol⁻¹ChemAxon
Polarizability102.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g4m-9100000003-15476a59d2389d71c70bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-5300000019-6661c8b1823b69eb1e01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ta-8830000019-35fa3750a0cf421648edJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-9600000014-c457633361b67fb7f98cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-069c-8300000039-89e8ab9fb8aab17abe41JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5600001529-fcfb845bf09065280726JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023974
KNApSAcK IDNot Available
Chemspider ID148400
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2304197
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound169691
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceD'Ari, Linda; Rabinowitz, Jesse C. Synthesis of folylpolyglutamates. Methods in Enzymology (1985), 113(Glutamate, Glutamine, Glutathione, Relat. Compd.), 169-82.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melse-Boonstra A, Verhoef P, West CE, van Rhijn JA, van Breemen RB, Lasaroms JJ, Garbis SD, Katan MB, Kok FJ: A dual-isotope-labeling method of studying the bioavailability of hexaglutamyl folic acid relative to that of monoglutamyl folic acid in humans by using multiple orally administered low doses. Am J Clin Nutr. 2006 Nov;84(5):1128-33. [PubMed:17093166 ]
  2. Hoffbrand AV, Tripp E, Lavoie A: Synthesis of folate polyglutamates in human cells. Clin Sci Mol Med. 1976 Jan;50(1):61-8. [PubMed:1082804 ]