Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for 5-Methyltetrahydropteroylpentaglutamate (HMDB02148)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:38 -0600
Update Date 2013-05-07 15:26:16 -0600
HMDB ID HMDB02148
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Methyltetrahydropteroylpentaglutamate
Description 5-Methyltetrahydropteroylpentaglutamate is a naturally occurring folate coenzyme; binds to an inhibits glyxine N-methyltransferase to regulate the availability of methyl groups in the liver (Journal of Biological Chemistry 264 (16): 9638-9642 JUN 5 1989 ).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5-Me-Thf(glu)5
  2. 5-Methyltetrahydropteroylpentaglutamate
  3. 5-Methyltetrahydropteroylpentaglutamic acid
Chemical Formula C40H53N11O18
Average Molecular Weight 975.9117
Monoisotopic Molecular Weight 975.357003947
IUPAC Name (2S,6R,11S)-2,11-diamino-6-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-[(4S)-4-amino-N-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-4-carboxybutanamido]-7-(carboxymethyl)-5,8-dioxododecanedioic acid
Traditional IUPAC Name (2S,6R,11S)-2,11-diamino-6-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-[(4S)-4-amino-N-[(4-{[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-4-carboxybutanamido]-7-(carboxymethyl)-5,8-dioxododecanedioic acid
CAS Registry Number 39555-46-9
SMILES CN1C(CNC2=CC=C(C=C2)C(=O)N(C(=O)CC[C@H](N)C(O)=O)[C@](C(CC(O)=O)C(=O)CC[C@H](N)C(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)OC(=O)CC[C@H](N)C(O)=O)CNC2=C1C(=O)N=C(N)N2
InChI Identifier InChI=1S/C40H53N11O18/c1-50-19(16-47-31-30(50)32(58)49-39(45)48-31)15-46-18-4-2-17(3-5-18)33(59)51(27(54)12-8-23(43)36(64)65)40(26(53)11-7-22(42)35(62)63,38(68)69-29(57)13-9-24(44)37(66)67)20(14-28(55)56)25(52)10-6-21(41)34(60)61/h2-5,19-24,46H,6-16,41-44H2,1H3,(H,55,56)(H,60,61)(H,62,63)(H,64,65)(H,66,67)(H4,45,47,48,49,58)/t19?,20?,21-,22-,23-,24-,40+/m0/s1
InChI Key WNRFVFOPCUPRFK-JPUKBXPDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Amino Fatty Acids
  • Aromatic Heteropolycyclic Compounds
  • Branched Fatty Acids
  • Heterocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
Substituents
  • Alpha Amino Acid Or Derivative
  • Alpha Aminoketone
  • Aminobenzamide
  • Aminopyrimidine
  • Benzamide
  • Benzoyl
  • Beta Aminoketone
  • Beta Keto Acid
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Acid Anhydride
  • Carboxylic Acid Imide, N Substituted
  • Gamma Aminoketone
  • Gamma Keto Acid
  • Hippurate
  • Ketone
  • N Acyl Alpha Amino Acid
  • N Epsilon Acetyl Lysine
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Pteroic Acid Derivative
  • Pyrimidine
  • Pyrimidone
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 0.47 g/L ALOGPS
LogP -2.84 ALOGPS
LogP -11 ChemAxon
LogS -3.32 ALOGPS
pKa (strongest acidic) 0.91 ChemAxon
pKa (strongest basic) 9.43 ChemAxon
Hydrogen Acceptor Count 27 ChemAxon
Hydrogen Donor Count 13 ChemAxon
Polar Surface Area 500.25 A2 ChemAxon
Rotatable Bond Count 29 ChemAxon
Refractivity 239.65 ChemAxon
Polarizability 92.65 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
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 FDB022868
KNApSAcK ID Not Available
Chemspider ID 168178 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02148 Link_out
Metagene Link HMDB02148 Link_out
METLIN ID 6511 Link_out
PubChem Compound 193793 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Bagley PJ, Selhub J: A common mutation in the methylenetetrahydrofolate reductase gene is associated with an accumulation of formylated tetrahydrofolates in red blood cells. Proc Natl Acad Sci U S A. 1998 Oct 27;95(22):13217-20. Pubmed: 9789068 Link_out