N(pros)-methyl-L-histidine (YMDB00703)

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Identification

YMDB ID

YMDB00703

Name

N(pros)-methyl-L-histidine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

3-Methylhistidine belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3-Methylhistidine is a very strong basic compound (based on its pKa). 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoate
(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
1-Methylhistidine
3-methyl-L-histidine
3-methylhistidine
3-N-Methyl-L-histidine
l-3-methylhistidine
L-Histidine, 3-methyl-
N-pros-Methyl-L-histidine
N(pai)-Methyl-L-histidine
N(pi)-methyl-l-histidine
N3-Methyl-L-histidine
pi-Methyl-L-histidine
Tau-Methyl-L-histidine
Tau-methylhistidine
N(pros)-Methyl-L-histidine
3-Methylhistidine hydride
3-Methylhistidine dihydrochloride
Pi methylhistidine
N(Pi)-methylhistidine
N Pi-methylhistidine

CAS number

368-16-1

Weight

Average: 169.1811
Monoisotopic: 169.085126611

InChI Key

JDHILDINMRGULE-LURJTMIESA-N

InChI

InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1

IUPAC Name

(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

Traditional IUPAC Name

3,methylhistidine

Chemical Formula

C₇H₁₁N₃O₂

SMILES

CN1C=NC=C1C[C@H](N)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:27596 )
L-histidine derivative (CHEBI:27596 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	200 mg/mL at 25 oC [BEILSTEIN]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.93 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.96 m³·mol⁻¹	ChemAxon
Polarizability	16.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	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

Not Available

KEGG Pathways

Histidine metabolism

ec00340

SMPDB Reactions

Not Available

KEGG Reactions

L-Histidine + S-Adenosylmethionine → S-Adenosylhomocysteine + N(pros)-methyl-L-histidine + hydron

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 (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-ab7d6324146b8775fe50	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-42443c78fdfca9db1926	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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 (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0900000000-e6ce7548fd6f09e2098f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-2900000000-77f55ec21b9e637c0148	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-25e42ab3c1bd0832a7fe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-3900000000-fb4a45b41e8cb903c156	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-0a98679ff9db2f56925a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-7b29b213a49dfa3c0f7d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0900000000-5a4990ec47e6292c0f7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-993e2b71358969de5168	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9500000000-1817d9d8adbfaf0595f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-2e05be86f146c22455ce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-2900000000-15f0e43eb0d06e7f3ef3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9200000000-5a1ab4d052e6ba4a76e4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0002-9000000000-c1951c88c84885804fb6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-4e0fea0fe9b1142db07b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0002-9000000000-a87ff5cc0642ea3af69c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0002-9000000000-28a73708493f968c2ac6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9800000000-6565ccf96757ef3bc08f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-2d351351f285b2188710	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-2ed34e7b458d9f8c092f	JSpectraViewer \| MoNA
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
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
2D NMR	[1H,13C] 2D 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
Gary, J. D., Lin, W. J., Yang, M. C., Herschman, H. R., Clarke, S. (1996). "The predominant protein-arginine methyltransferase from Saccharomyces cerevisiae." J Biol Chem 271:12585-12594.8647869

Synthesis Reference:

Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.

External Links:

Resource	Link
CHEBI ID	27596
HMDB ID	HMDB00479
Pubchem Compound ID	64969
Kegg ID	C01152
ChemSpider ID	58494
FOODB ID	FDB093613
Wikipedia ID	3-Methylhistidine
BioCyc ID	Not Available

Enzymes

Protein Details

1. HNRNP arginine N-methyltransferase

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates arginines in a variety of RNA-binding proteins. Methylates NOP3. Can catalyze both the mono- and asymmetric dimethylation
Gene Name:: HMT1
Uniprot ID:: P38074
Molecular weight:: 39785.80078

Reactions

Structure for #<Compound:0xae293c64>

Enzymes

Reactions