tetrahydropteroyltri-L-glutamate (PAMDB003550)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003550
Identification
Name: tetrahydropteroyltri-L-glutamate
Description:Tetrahydropteroyltri-L-glutamate is an intermediate in the synthesis of methionine. It is a substrate for the enzyme 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase which catalyzes the reaction 5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-(4S)-4-(4S)-4-4-(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-Pteridin-6-ylmethylaminobenzoylamino-4-carboxybutanoylamino-4-carboxybutanoylaminopentanedioate
  • (2S)-2-(4S)-4-(4S)-4-4-(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-ylmethylaminobenzoylamino-4-carboxybutanoylamino-4-carboxybutanoylaminopentanedioic acid
  • N-4-({(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-g-glutamyl-L-g-glutamyl-L-glutamate
  • N-4-({(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-g-glutamyl-L-g-glutamyl-L-glutamic acid
  • N-4-({(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamate
  • N-4-({(6S)-2-Amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acid
  • N-4-({(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamate
  • N-4-({(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinylmethyl}amino)benzoyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid
  • Tetrahydropteroyltri-L-glutamate
  • Tetrahydropteroyltri-L-glutamic acid
Chemical Formula: C29H37N9O12
Average Molecular Weight: 703.6572
Monoisotopic Molecular Weight: 703.256167693
InChI Key: RXWVHRYZTWZATH-XSLAGTTESA-N
InChI: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)/t15-,16-,17-,18-/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-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: (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid
SMILES:NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzamides
Direct Parent Hippuric acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Pterin
  • Pteridine
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Aminobenzamide
  • Phenylalkylamine
  • Substituted aniline
  • Benzoyl
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Pyrimidine
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.359 mg/mLALOGPS
logP-1.6ALOGPS
logP-6.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area340.07 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity177.56 m3·mol-1ChemAxon
Polarizability69.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
5-methyltetrahydropteroyltri-L-glutamate + L-Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > L-Methionine + tetrahydropteroyltri-L-glutamate
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0430109000-eac2681831f71dca6e8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0950105000-4fcd371853d69be99f61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0930101000-93bebce6dc25dfe950c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kal-0000009200-1222553f516303fcc67bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-0110119000-86fae98cd0220bb8d84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054p-6941212000-00e3dffa2369077ff1f0View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17420
HMDB IDHMDB12290
Pubchem Compound ID16722112
Kegg IDC04144
ChemSpider ID17625690
Wikipedia IDNot Available
BioCyc IDCPD-1302
EcoCyc IDCPD-1302