5-Methyltetrahydropteroyltri-L-glutamic acid (YMDB00518)

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Identification

YMDB ID

YMDB00518

Name

5-Methyltetrahydropteroyltri-L-glutamic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

5-Methyltetrahydropteroyltri-L-glutamic acid belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) . 5-Methyltetrahydropteroyltri-L-glutamic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on 5-Methyltetrahydropteroyltri-L-glutamic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

5-Methyltetrahydropteroyltri-L-glutamate
5-methyltetrahydropteroyltri-L-glutamic acid
5-Methyl-5,6,7,8-tetrahydropteroyl tri-gamma-L-glutamate
5-Methyl-5,6,7,8-tetrahydropteroyl tri-γ-L-glutamate
5-Methyltetrahydrofolate triglutamate
5-Methyltetrahydropteroyl-gamma-glutamyl-gamma-glutamylglutamic acid
5-Methyltetrahydropteroyl-γ-glutamyl-γ-glutamylglutamic acid

CAS number

Not Available

Weight

Average: 717.6838
Monoisotopic: 717.271817757

InChI Key

HVRNKDVLFAVCJF-VJANTYMQSA-N

InChI

InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/t16-,17-,18-,19-/m0/s1

IUPAC Name

(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-5-methyl-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-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid

Chemical Formula

C₃₀H₃₉N₉O₁₂

SMILES

CN1[C@@H](CNC2=CC=C(C=C2)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)CNC2=C1C(=O)NC(N)=N2

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) .

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids and derivatives

Alternative Parents

Substituents

Tetrahydrofolic acid or derivatives
Alpha-oligopeptide
Gamma-glutamyl alpha-amino acid
Glutamic acid or derivatives
Glutamine or derivatives
Tetracarboxylic acid or derivatives
N-acyl-l-alpha-amino acid
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Aminobenzamide
Alpha-amino acid or derivatives
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Tertiary aliphatic/aromatic amine
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Dialkylarylamine
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Pyrimidine
Monocyclic benzene moiety
Benzenoid
N-acyl-amine
Fatty acyl
Fatty amide
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Tertiary amine
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Primary amine
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydropteroyltri-L-glutamate (CHEBI:17614 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-3.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	3.14	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	331.28 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	182.86 m³·mol⁻¹	ChemAxon
Polarizability	70.68 Å³	ChemAxon
Number of Rings	3	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

Organoleptic Properties

Not Available

SMPDB Pathways

Methionine metabolism and salvage	PW002384
Selenocompound metabolism	PW002472

KEGG Pathways

Selenocompound metabolism

ec00450

SMPDB Reactions

Not Available

KEGG Reactions

L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid → L-Methionine + Tetrahydropteroyltri-L-glutamate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0732118900-53d55fe9c0863d97f51f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0932104100-d16b89e4058f4ac3aa4c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1921101000-70b11d23c3858386d9c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00r2-0000009200-85df402e63838ca104ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fi1-0110019000-44613760172916ef7e66	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-5931213000-75cc50202a2eca9054cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ikc-0429311800-370ce9231396acda8d92	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01u3-1625490000-4b2f69d8a822fdbfcca9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02cu-1905000000-a42458750a4d98ede330	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0010009100-0dc6b367fdbdca7547fc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zir-0330119000-1542d290911c87efd051	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-1913110000-8e9ec4663cc7affb6895	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Csaikl, U., Csaikl, F. (1986). "Molecular cloning and characterization of the MET6 gene of Saccharomyces cerevisiae." Gene 46:207-214.3542720
UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17614
HMDB ID	HMDB12177
Pubchem Compound ID	16722111
Kegg ID	C04489
ChemSpider ID	17625689
FOODB ID	FDB028831
Wikipedia ID	Not Available
BioCyc ID	CPD-1302

Enzymes

Protein Details

1. 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase

General function:: Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:: Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:: MET6
Uniprot ID:: P05694
Molecular weight:: 85859.20313

Reactions

5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine → tetrahydropteroyltri-L-glutamate + L-methionine.

5-Methyltetrahydropteroyltri-L-glutamic acid (YMDB00518)

Structure for #<Compound:0xb040dfc0>

Enzymes

Reactions