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Showing NP-Card for n-methyl-l-histidine (NP0309743)

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Record Information
Version2.0
Created at2022-09-11 04:33:13 UTC
Updated at2022-09-11 04:33:13 UTC
NP-MRD IDNP0309743
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-methyl-l-histidine
DescriptionN(alpha)-methyl-L-histidine, also known as methylhistidines, 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. n-methyl-l-histidine was first documented in 2010 (PMID: 20420435). Based on a literature review very few articles have been published on N(alpha)-methyl-L-histidine (PMID: 24834460).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0309743 (n-methyl-l-histidine)


  Mrv1652309112206332D          

 12 12  0  0  1  0            999 V2000
   -0.8612    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0309743 (n-methyl-l-histidine)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.3033    1.4120    0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762    0.5509    0.9295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070   -0.2575   -0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3491   -1.0877   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -0.2972    0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808    0.0882    1.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    0.8046    1.0939 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.8800   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    0.1946   -0.8355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182   -1.2052   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -1.2040    0.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968   -2.0975   -1.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523    1.0195    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826    1.5168   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1677    2.4338    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724    1.1120    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339    0.4013   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -1.8404    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4057   -1.6892   -1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -0.1084    2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    1.3945   -0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980    0.1108   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3201   -2.1320   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  3 10  1  0
 10 12  1  0
 10 11  2  0
  9  5  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  6
  4 18  1  0
  4 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0309743 (n-methyl-l-histidine)


  Mrv1652309112206332D          

 12 12  0  0  1  0            999 V2000
   -0.8612    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](CC1=CN=CN1)C(O)=O

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

> <INCHI_KEY>
CYZKJBZEIFWZSR-LURJTMIESA-N

> <FORMULA>
C7H11N3O2

> <MOLECULAR_WEIGHT>
169.184

> <EXACT_MASS>
169.085126606

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.667577146562923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(1H-imidazol-5-yl)-2-(methylamino)propanoic acid

> <JCHEM_LOGP>
-3.400392431968617

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941745878285161

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5500850783677653

> <JCHEM_PKA_STRONGEST_BASIC>
10.244558402713551

> <JCHEM_POLAR_SURFACE_AREA>
78.01

> <JCHEM_REFRACTIVITY>
42.833600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-L-histidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0309743 (n-methyl-l-histidine)

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PDB for NP0309743 (n-methyl-l-histidine)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.274   5.930   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.941   4.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0309743 (n-methyl-l-histidine)
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SMILES for NP0309743 (n-methyl-l-histidine)
CN[C@@H](CC1=CN=CN1)C(O)=O
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INCHI for NP0309743 (n-methyl-l-histidine)
InChI=1S/C7H11N3O2/c1-8-6(7(11)12)2-5-3-9-4-10-5/h3-4,6,8H,2H2,1H3,(H,9,10)(H,11,12)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
N-Methyl-L-histidineChEBI
Nalpha-methylhistidineChEBI
N(a)-Methyl-L-histidineGenerator
N(Α)-methyl-L-histidineGenerator
MethylhistidineMeSH
MethylhistidinesMeSH
Chemical FormulaC7H11N3O2
Average Mass169.1840 Da
Monoisotopic Mass169.08513 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CN[C@@H](CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C7H11N3O2/c1-8-6(7(11)12)2-5-3-9-4-10-5/h3-4,6,8H,2H2,1H3,(H,9,10)(H,11,12)/t6-/m0/s1
InChI KeyCYZKJBZEIFWZSR-LURJTMIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentHistidine and derivatives  
Alternative Parents
Substituents
  • Histidine or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Imidazolyl carboxylic acid derivative
    • 

  • Aralkylamine
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Heteroaromatic compound
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID81836  
KEGG Compound IDC03298  
BioCyc IDCPD-15285  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90638  
PDB IDNot Available
ChEBI ID50601  
Good Scents IDNot Available
References
General References
  1. Gao Y, Lu Y, Huang S, Gao L, Liang X, Wu Y, Wang J, Huang Q, Tang L, Wang G, Yang F, Hu S, Chen Z, Wang P, Jiang Q, Huang R, Xu Y, Yang X, Ong CN: Identifying early urinary metabolic changes with long-term environmental exposure to cadmium by mass-spectrometry-based metabolomics. Environ Sci Technol. 2014 Jun 3;48(11):6409-18. doi: 10.1021/es500750w. Epub 2014 May 16. [PubMed:24834460  ] 
  2. Sonntag T, Kunert C, Dunkel A, Hofmann T: Sensory-guided identification of N-(1-methyl-4-oxoimidazolidin-2-ylidene)-alpha-amino acids as contributors to the thick-sour and mouth-drying orosensation of stewed beef juice. J Agric Food Chem. 2010 May 26;58(10):6341-50. doi: 10.1021/jf100591c. [PubMed:20420435  ] 
  3. LOTUS database [Link]