P. aeruginosa Metabolome Database: Tetrahydropteroyltri-L-glutamic acid (PAMDB000283)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000283

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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Tetrahydropteroyltri-L-glutamate
Tetrahydropteroyltri-L-glutamic acid
THPTGlu

Chemical Formula:

C₂₄H₃₄N₈O₁₂

Average Molecular Weight:

626.5732

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Substituents

Hexacarboxylic acid or derivatives
Biopterin
Alpha-amino acid ester
Pterin
Pteridine
Alpha-amino acid or derivatives
Fatty acid ester
Amino fatty acid
Fatty acyl
Pyrimidine
Heteroaromatic compound
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-2.043	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.154 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	163.61 m³·mol^-1	ChemAxon
Polarizability	59.11 Å³	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

Pathways:

Cysteine and methionine metabolism pae00270
Metabolic pathways pae01100
Selenoamino acid metabolism pae00450

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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

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

Tetrahydropteroyltri-L-glutamic acid (PAMDB000283)

Structure for Tetrahydropteroyltri-L-glutamic acid (PAMDB000283)