2-azaniumyl-3-(1-methyl-1H-imidazol-4-yl)propanoate
Basic information
- CAS
332-80-9- Standard SMILES
Cn1cnc(CC(N)C(=O)O)c1- InChIKey
BRMWTNUJHUMWMS-UHFFFAOYSA-N- Molecular formula
- C7H11N3O2
- Average molar mass
- 169.18 g/mol
- Monoisotopic mass
- 169.0851266
Overview
1-methylhistidine is a methylhistidine in which the methyl group is located at N-1. It has a role as a human urinary metabolite. It is a methylhistidine and a non-proteinogenic alpha-amino acid. It is a tautomer of a 1-methylhistidine zwitterion.
Names & identifiers
- Preferred name
- 2-azaniumyl-3-(1-methyl-1H-imidazol-4-yl)propanoate
- IUPAC
- 2-amino-3-(1-methylimidazol-4-yl)propanoic acid
- English name
- 1-Methyl-L-histidine
- Molecular formula
- C7H11N3O2
- Molecular weight
- 169.18
Names & synonyms
2-amino-3-(1-methylimidazol-4-yl)propanoic acid2-azaniumyl-3-(1-methyl-1H-imidazol-4-yl)propanoateRefChem:10622752-azaniumyl-3-(1-methylimidazol-4-yl)propanoateH-D-His(tau-Me)-OH28095-60-5N|O-Methyl-L-histidine1-methyl-DL-histidineSCHEMBL522151-methylhistidine (DL-form)CHEMBL45557CERAPP_27215
Show more names
1-METHYLHISTIDINEHis(1-Me)-OHNSC 524367H-His(t-Me)-OHL-His(1-Me)-OHH-HIS(1-ME)-OHH-HIS(3-ME)-OHH-His(τ-Me)-OHH-HIS(PI-ME)-OHL-His(Nim-Me)-OH
DTXSID40861879BRMWTNUJHUMWMS-UHFFFAOYSA-NEBC-47219NSC524367AKOS015915209HR-0365DB-048378NS00010105
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 81.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 174
Physicochemical properties
- Melting point
- 240 °C · ~240 °C (dec.) (lit.)
- alpha
- -24 · -24 º (c=2% in H2O)
- Boiling point
- 298.47 °C · 298.47°C (rough estimate)
- Density
- 1.2509 · 1.2509 (rough estimate)
- refractive index
- 1.595 · 1.5950 (estimate)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- Methanol (Slightly), Water (Slightly, Sonicated)
- pka
- 1.69 · 1.69(at 25℃)
- form
- Solid
- color
- Off-White to Pale Beige
- optical activity
- 20 · [α]20/D 24±1°, c = 2% in H2O
- BRN
- 9727 · 9727
- Stability
- Hygroscopic
- Major Application
- peptide synthesis
- InChI
- 1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29332900
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-24/25-22
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesThe urinary 1- and 3-methylhistidine (1- and 3-MH) metabolites as potential biomarkers of skeletal muscle toxicity. These metabolites were highly correlated to sex-, dose-, and time-dependent development of cerivastatin-induced myotoxicity. Natural but non-proteinogenic amino acid; employed as index of muscle protein breakdown.
Additional notes
DefinitionChEBI: N(tele)-methyl-L-histidine is a L-histidine derivative in which the methyl group is at N(tele)-position. It has a role as a human metabolite. It is a L-histidine derivative and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a N(tele)-methyl-L-histidine zwitterion.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…