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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:50 -0600
Update Date	2015-06-03 15:53:48 -0600
Secondary Accession Numbers	ECMDB01174
Identification
Name:	Tetrahydropteroyltri-L-glutamic acid
Description	Tetrahydropteroyltri-L-glutamic acid is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. tetrahydropteroyltri-L-glutamic acid (CHEBI:17420) is a tetrahydropteroyltri-L-glutamate (CHEBI:26920) tetrahydropteroyltri-L-glutamic acid (CHEBI:17420) is conjugate acid of tetrahydropteroyltri-L-glutamate (CHEBI:58140)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa7814e88> Close
Synonyms:	Tetrahydropteroyltri-L-glutamate Tetrahydropteroyltri-L-glutamic acid THPTGlu
Chemical Formula:	C24H34N8O12
Weight:	Average: 626.5732 Monoisotopic: 626.229618592
InChI Key:	XPPZDBCBKYATPW-MQXOEPKGSA-N
InChI:	InChI=1S/C24H34N8O12/c1-9(42-21(39)10(25)2-5-14(33)34)18(43-22(40)11(26)3-6-15(35)36)13-8-29-19-17(30-13)20(32-24(28)31-19)44-23(41)12(27)4-7-16(37)38/h8-12,18,30H,2-7,25-27H2,1H3,(H,33,34)(H,35,36)(H,37,38)(H3,28,29,31,32)/t9?,10-,11-,12-,18?/m0/s1
CAS number:	Not Available
IUPAC Name:	(4S)-4-amino-5-[(1-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-1-(4-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-2-imino-1,2,5,8-tetrahydropteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid
Traditional IUPAC Name:	(4S)-4-amino-5-[(1-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-1-(4-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-2-imino-5,8-dihydro-1H-pteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid
SMILES:	[H][C@](N)(CCC(O)=O)C(=O)OC1=NC(=N)NC2=C1NC(=CN2)C([H])(OC(=O)[C@@]([H])(N)CCC(O)=O)C([H])(C)OC(=O)[C@@]([H])(N)CCC(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Hexacarboxylic acids and derivatives
Direct Parent	Hexacarboxylic acids and derivatives
Alternative Parents	Biopterins and derivatives Glutamic acid and derivatives Alpha amino acid esters Secondary alkylarylamines Amino fatty acids Aminopyrimidines and derivatives Fatty acid esters Imidolactams Heteroaromatic compounds Amino acids Carboxylic acid esters Azacyclic compounds Enamines Carboxylic acids Organopnictogen compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Monoalkylamines
Substituents	Hexacarboxylic acid or derivatives Biopterin Glutamic acid or derivatives Alpha-amino acid ester Pterin Alpha-amino acid or derivatives Pteridine Fatty acid ester Amino fatty acid Aminopyrimidine Secondary aliphatic/aromatic amine Imidolactam Pyrimidine Fatty acyl Heteroaromatic compound Amino acid Amino acid or derivatives Carboxylic acid ester Secondary amine Carboxylic acid Enamine Organoheterocyclic compound Azacycle Organic nitrogen compound Primary aliphatic amine Organonitrogen compound Organooxygen compound Carbonyl group Primary amine Hydrocarbon derivative Organic oxide Organopnictogen compound Amine Organic oxygen compound Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -2.043 PhysProp
Predicted Properties	Property Value Source Water Solubility 0.15 g/L ALOGPS logP -3.5 ALOGPS logP -10 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 2.44 ChemAxon pKa (Strongest Basic) 8.52 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 341.16 Ų ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 163.61 m³·mol⁻¹ ChemAxon Polarizability 59.11 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	5-Methyltetrahydropteroyltri-L-glutamic acid + L-Homocysteine <> Tetrahydropteroyltri-L-glutamic acid + L-Methionine Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid <> Selenomethionine + Tetrahydropteroyltri-L-glutamic acid
SMPDB Pathways:	Not Available
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 Selenoamino acid metabolism ec00450
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_25) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0btc-0000798000-a39b992c09f3cd640b11 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0f89-4501941000-dc29949cddfbf159e32f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0zir-5421910000-0a69615ec7aa6f337088 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0400935000-f1aa921f4b3d29deb419 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-0601912000-a85d64e7980866e2fb68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00xs-2709200000-f23ed20992da7d0e757f View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17420 HMDB ID Not Available Pubchem Compound ID 16722112 Kegg ID C04144 ChemSpider ID 389223 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes