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Showing NP-Card for 3-Methyl-L-histidine (NP0338703)

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Record Information
Version2.0
Created at2024-09-11 17:08:54 UTC
Updated at2024-09-11 17:08:54 UTC
NP-MRD IDNP0338703
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyl-L-histidine
Description 3-Methyl-L-histidine was first documented in 2008 (PMID: 19195377). Based on a literature review a significant number of articles have been published on 3-Methyl-L-histidine (PMID: 28974740) (PMID: 38814331) (PMID: 38046955) (PMID: 37051694) (PMID: 36694927) (PMID: 35621964).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338703 (3-Methyl-L-histidine)


  Mrv2104 05262319412D          

 12 12  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -0.4747    0.0000 N   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
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.0352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  9  2  0  0  0  0
  4 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
M  END
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3D MOL for NP0338703 (3-Methyl-L-histidine)

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3D SDF for NP0338703 (3-Methyl-L-histidine)

  Mrv2104 05262319412D          

 12 12  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -0.4747    0.0000 N   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
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.0352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  9  2  0  0  0  0
  4 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338703

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC=C1CC(N)C(O)=O

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

> <INCHI_KEY>
JDHILDINMRGULE-UHFFFAOYNA-N

> <FORMULA>
C7H11N3O2

> <MOLECULAR_WEIGHT>
169.184

> <EXACT_MASS>
169.085126606

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.746582365362123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

> <JCHEM_LOGP>
-3.3988714686124912

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9164297170788498

> <JCHEM_PKA_STRONGEST_BASIC>
9.406155138702497

> <JCHEM_POLAR_SURFACE_AREA>
81.14

> <JCHEM_REFRACTIVITY>
42.95570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-methylhistidine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0338703 (3-Methyl-L-histidine)
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PDB for NP0338703 (3-Methyl-L-histidine)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.260   1.096   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.475  -0.886   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       1.060   2.080   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -5.404   0.066   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.580   2.602   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    5    6                                                       
CONECT    3    5    9                                                       
CONECT    4    9   10                                                       
CONECT    5    2    3   10                                                  
CONECT    6    2    7    8                                                  
CONECT    7    6   11   12                                                  
CONECT    8    6                                                            
CONECT    9    3    4                                                       
CONECT   10    1    4    5                                                  
CONECT   11    7                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0338703 (3-Methyl-L-histidine)
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SMILES for NP0338703 (3-Methyl-L-histidine)
CN1C=NC=C1CC(N)C(O)=O
Download
INCHI for NP0338703 (3-Methyl-L-histidine)
InChI=1/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H11N3O2
Average Mass169.1840 Da
Monoisotopic Mass169.08513 Da
IUPAC Name2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name3-methylhistidine
CAS Registry NumberNot Available
SMILES
CN1C=NC=C1CC(N)C(O)=O
InChI Identifier
InChI=1/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)
InChI KeyJDHILDINMRGULE-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP-3.4ChemAxon
pKa (Strongest Acidic)1.92ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.96 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylhistidine  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kaneko J, Enya A, Enomoto K, Ding Q, Hisatsune T: Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AbetaPPswe/PSEN1dE9 Alzheimer's-model mice. Sci Rep. 2017 Oct 3;7(1):12571. doi: 10.1038/s41598-017-12785-7. [PubMed:28974740  ] 
  2. Merkhassine M, Coch RW, Frederick CE, Bennett LL, Peng SA, Morse B, Cummings BP, Loftus JP: Glucagon infusion alters the circulating metabolome and urine amino acid excretion in dogs. J Endocrinol. 2024 Jun 27;262(2):e240051. doi: 10.1530/JOE-24-0051. Print 2024  Aug 1. [PubMed:38814331  ] 
  3. Shi C, Yu Z, Wang Z, Ning R, Huang C, Gao Y, Wang F: Dietary supplementation with pyrroloquinoline quinone promotes growth, relieves weaning stress, and regulates metabolism of piglets compared with adding zinc oxide. Anim Nutr. 2023 Oct 4;15:409-419. doi: 10.1016/j.aninu.2023.06.015. eCollection  2023 Dec. [PubMed:38046955  ] 
  4. Taylor CJ, Hardy FJ, Burke AJ, Bednar RM, Mehl RA, Green AP, Lovelock SL: Engineering mutually orthogonal PylRS/tRNA pairs for dual encoding of functional histidine analogues. Protein Sci. 2023 May;32(5):e4640. doi: 10.1002/pro.4640. [PubMed:37051694  ] 
  5. Kino K, Komabayashi T, Hashida A, Kuramoto A: Improving the enzymatic activity of l-amino acid alpha-ligase for imidazole dipeptide production by site-directed mutagenesis. Biosci Biotechnol Biochem. 2023 Mar 21;87(4):389-394. doi: 10.1093/bbb/zbac213. [PubMed:36694927  ] 
  6. Yang M, Sun L, Kawabata Y, Murayama F, Maegawa T, Nikawa T, Hirasaka K: Balenine, Imidazole Dipeptide Promotes Skeletal Muscle Regeneration by Regulating Phagocytosis Properties of Immune Cells. Mar Drugs. 2022 May 5;20(5):313. doi: 10.3390/md20050313. [PubMed:35621964  ] 
  7. Ding Y, Bu F, Chen T, Shi G, Yuan X, Feng Z, Duan Z, Wang R, Zhang S, Wang Q, Zhou J, Chen Y: A next-generation probiotic: Akkermansia muciniphila ameliorates chronic stress-induced depressive-like behavior in mice by regulating gut microbiota and metabolites. Appl Microbiol Biotechnol. 2021 Nov;105(21-22):8411-8426. doi:  10.1007/s00253-021-11622-2. Epub 2021 Oct 7. [PubMed:34617139  ] 
  8. Wang-Eckhardt L, Bastian A, Bruegmann T, Sasse P, Eckhardt M: Carnosine synthase deficiency is compatible with normal skeletal muscle and olfactory function but causes reduced olfactory sensitivity in aging mice. J Biol Chem. 2020 Dec 11;295(50):17100-17113. doi: 10.1074/jbc.RA120.014188. Epub  2020 Oct 9. [PubMed:33040025  ] 
  9. Alkhatib A, Feng WH, Huang YJ, Kuo CH, Hou CW: Anserine Reverses Exercise-Induced Oxidative Stress and Preserves Cellular Homeostasis in Healthy Men. Nutrients. 2020 Apr 19;12(4):1146. doi: 10.3390/nu12041146. [PubMed:32325914  ] 
  10. Gan F, Liu R, Wang F, Schultz PG: Functional Replacement of Histidine in Proteins To Generate Noncanonical Amino Acid Dependent Organisms. J Am Chem Soc. 2018 Mar 21;140(11):3829-3832. doi: 10.1021/jacs.7b13452. Epub  2018 Mar 12. [PubMed:29509426  ] 
  11. Matysiak J, Derezinski P, Klupczynska A, Matysiak J, Kaczmarek E, Kokot ZJ: Effects of a honeybee sting on the serum free amino acid profile in humans. PLoS One. 2014 Jul 29;9(7):e103533. doi: 10.1371/journal.pone.0103533.  eCollection 2014. [PubMed:25072247  ] 
  12. Bellia F, Vecchio G, Rizzarelli E: Carnosinases, their substrates and diseases. Molecules. 2014 Feb 21;19(2):2299-329. doi: 10.3390/molecules19022299. [PubMed:24566305  ] 
  13. Patel SS, Molnar MZ, Tayek JA, Ix JH, Noori N, Benner D, Heymsfield S, Kopple JD, Kovesdy CP, Kalantar-Zadeh K: Serum creatinine as a marker of muscle mass in chronic kidney disease: results of a cross-sectional study and review of literature. J Cachexia Sarcopenia Muscle. 2013 Mar;4(1):19-29. doi:  10.1007/s13539-012-0079-1. Epub 2012 Jul 10. [PubMed:22777757  ] 
  14. Park JY, Back SS, Chun BS: Protein properties of mackerel viscera extracted by supercritical carbon dioxide. J Environ Biol. 2008 Jul;29(4):443-8. [PubMed:19195377  ]