Human Metabolome Database Version 3.5

Showing metabocard for Tetrahydrofolyl-[Glu](n) (HMDB06826)

Record Information
Version 3.5
Creation Date 2008-08-12 09:17:10 -0600
Update Date 2013-02-08 17:15:23 -0700
HMDB ID HMDB06826
Secondary Accession Numbers None
Metabolite Identification
Common Name Tetrahydrofolyl-[Glu](n)
Description Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9]. Sample structure image shows the case when n=3.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Tetrahydrofolyl-[Glu](N+1)
  2. Tetrahydropteroyl-[gamma-Glu]N
  3. Tetrahydropteroyl-[gamma-Glu]N+1
  4. THF-L-Glutamic acid
  5. THF-polyglutamate
Chemical Formula C29H37N9O12
Average Molecular Weight 703.6572
Monoisotopic Molecular Weight 703.256167693
IUPAC Name 2-(4-{4-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
Traditional IUPAC Name 2-(4-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
CAS Registry Number Not Available
SMILES NC1=NC(=O)C2=C(NCC(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)N2)N1
InChI Identifier InChI=1S/C29H37N9O12/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/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)
InChI Key RXWVHRYZTWZATH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • tetrahydropteroyltri-L-glutamate(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Aminobenzamide
  • Aminopyrimidine
  • Benzamide
  • Benzoyl
  • Carboxamide Group
  • Carboxylic Acid
  • Hippurate
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Polyamine
  • Pteroic Acid Derivative
  • Pyrimidine
  • Pyrimidone
  • Secondary Carboxylic Acid Amide
Direct Parent Folic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.36 g/L ALOGPS
LogP -1.64 ALOGPS
LogP -6.1 ChemAxon
LogS -3.29 ALOGPS
pKa (strongest acidic) 3.07 ChemAxon
pKa (strongest basic) 3.58 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 340.07 A2 ChemAxon
Rotatable Bond Count 19 ChemAxon
Refractivity 177.56 ChemAxon
Polarizability 67.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pterine Biosynthesis SMP00005 map00790 Link_out
Folate Metabolism SMP00053 map00670 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024106
KNApSAcK ID Not Available
Chemspider ID 21231977 Link_out
KEGG Compound ID C03541 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06826 Link_out
Metagene Link HMDB06826 Link_out
METLIN ID Not Available
PubChem Compound 45479706 Link_out
PDB ID Not Available
ChEBI ID 27650 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Folylpolyglutamate synthase, mitochondrial
Reactions: Not Available
Gene Name: FPGS
Uniprot ID: Q05932 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-glutamyl hydrolase
Reactions: Not Available
Gene Name: GGH
Uniprot ID: Q92820 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA