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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-03-09 15:41:08 UTC
Update Date2019-07-23 05:45:10 UTC
HMDB IDHMDB0001902
Secondary Accession Numbers
  • HMDB01902
Metabolite Identification
Common NamePteroyltriglutamic acid
DescriptionPteroyltriglutamic acid is a crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. (http://medical-dictionary.thefreedictionary.com/pteropterin). As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071 ). Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney. (PMID: 10598552 ).
Structure
Data?1563860710
Synonyms
ValueSource
PteroyltriglutamateGenerator
N-[N-(N-Pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-glutamic acidHMDB
Folic acid diglutamateHMDB
N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acidHMDB
N-[N-[N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-glutamic acidHMDB
PteropterinHMDB
Pteroyl-gamma-triglutamic acidHMDB
Pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acidHMDB
Pteroyltri-gamma-L-glutamic acidHMDB
TeropterinHMDB
Pteropterin, sodium saltHMDB
Pteroyl-gamma-glutamyl-gamma-glutamylglutamic acidHMDB
2-{[4-carboxy-4-({4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene}amino)-1-hydroxybutylidene]amino}pentanedioateGenerator
Pteroyltriglutamic acidMeSH
Chemical FormulaC29H33N9O12
Average Molecular Weight699.6254
Monoisotopic Molecular Weight699.224867565
IUPAC Name2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
Traditional Name2-(4-{4-[(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
CAS Registry Number89-38-3
SMILES
NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1
InChI Identifier
InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)
InChI KeyWOLQREOUPKZMEX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Pterin
  • Alpha-amino acid or derivatives
  • Pteridine
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Pyrimidone
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Pyrazine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 5 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP-0.55ALOGPS
logP-2.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)2.08ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area341.79 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity167.19 m³·mol⁻¹ChemAxon
Polarizability67.38 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0221229000-c23f869dc13b1d95272aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0330009000-e987962787f2029e2f08JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0960106000-21f9d9b3b6972db9bc7cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0941002000-891cdeb849daa1e9d839JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f8a-0000009000-bd7ecf2c2eeac6ea62e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gws-0110019000-44f0bdd173f7125a9395JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f97-5941201000-3d500662a3c45848f410JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB022730
KNApSAcK IDNot Available
Chemspider ID6702
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6381
PubChem Compound6968
PDB IDNot Available
ChEBI ID554079
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hendel L, Hendel J, Joergensen I: Enterocyte function in progressive systemic sclerosis as estimated by the deconjugation of pteroyltriglutamate to folic acid. Gut. 1987 Apr;28(4):435-8. [PubMed:3583071 ]
  2. Galivan J, Ryan T, Rhee M, Yao R, Chave K: Glutamyl hydrolase: properties and pharmacologic impact. Semin Oncol. 1999 Apr;26(2 Suppl 6):33-7. [PubMed:10598552 ]