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Showing NP-Card for n,n-dimethyl-l-histidine (NP0288101)

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Record Information
Version1.0
Created at2022-09-09 17:40:36 UTC
Updated at2022-09-09 17:40:36 UTC
NP-MRD IDNP0288101
Secondary Accession NumbersNone
Natural Product Identification
Common Namen,n-dimethyl-l-histidine
DescriptionN(alpha),N(alpha)-dimethyl-L-histidine, also known as N(α),N(α)-dimethyl-L-histidine, 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(alpha),N(alpha)-dimethyl-L-histidine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1970 (PMID: 5438052). Based on a literature review a significant number of articles have been published on N(alpha),N(alpha)-dimethyl-L-histidine (PMID: 36113990) (PMID: 36113989) (PMID: 36113988) (PMID: 36113987) (PMID: 36113986) (PMID: 36113984).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0288101 (n,n-dimethyl-l-histidine)


  Mrv1652309092219402D          

 13 13  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
    0.5678    3.5893    0.0000 C   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
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0288101 (n,n-dimethyl-l-histidine)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.8297    0.4162   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.4417   -0.3037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461   -1.8248   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -0.1408    0.2460 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177   -0.1783   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019    0.0926   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    1.2791   -0.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492    1.0270   -0.0008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -0.3017    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246   -0.8668   -0.2113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294    1.3184    0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6468    2.1999   -0.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782    1.7178    1.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7251    0.0034   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192    0.4010    1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338    1.4633   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.5069   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639   -2.0349   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -1.9295    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080   -0.7442    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379   -1.1847   -1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    0.5267   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1573    2.2674   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -0.8021    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -1.8886   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930    2.1322    2.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  4 11  1  0
 11 13  1  0
 11 12  2  0
 10  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
M  END
Download

3D SDF for NP0288101 (n,n-dimethyl-l-histidine)


  Mrv1652309092219402D          

 13 13  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
    0.5678    3.5893    0.0000 C   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
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288101

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H13N3O2/c1-11(2)7(8(12)13)3-6-4-9-5-10-6/h4-5,7H,3H2,1-2H3,(H,9,10)(H,12,13)/t7-/m0/s1

> <INCHI_KEY>
IMOBSLOLPCWZKQ-ZETCQYMHSA-N

> <FORMULA>
C8H13N3O2

> <MOLECULAR_WEIGHT>
183.211

> <EXACT_MASS>
183.100776671

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.348098461634557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.2556976866028733

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.940947785790332

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3740599692916855

> <JCHEM_PKA_STRONGEST_BASIC>
9.794987452636432

> <JCHEM_POLAR_SURFACE_AREA>
69.22

> <JCHEM_REFRACTIVITY>
48.1283

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N,N-dimethyl-L-histidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0288101 (n,n-dimethyl-l-histidine)

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PDB for NP0288101 (n,n-dimethyl-l-histidine)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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       1.060   6.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.941   4.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0288101 (n,n-dimethyl-l-histidine)
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SMILES for NP0288101 (n,n-dimethyl-l-histidine)
CN(C)[C@@H](CC1=CN=CN1)C(O)=O
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INCHI for NP0288101 (n,n-dimethyl-l-histidine)
InChI=1S/C8H13N3O2/c1-11(2)7(8(12)13)3-6-4-9-5-10-6/h4-5,7H,3H2,1-2H3,(H,9,10)(H,12,13)/t7-/m0/s1
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View in JSmol
Synonyms
ValueSource
Nalpha,nalpha-dimethyl-L-histidineChEBI
N(a),N(a)-Dimethyl-L-histidineGenerator
N(Α),N(α)-dimethyl-L-histidineGenerator
Chemical FormulaC8H13N3O2
Average Mass183.2110 Da
Monoisotopic Mass183.10078 Da
IUPAC Name(2S)-2-(dimethylamino)-3-(1H-imidazol-5-yl)propanoic acid
Traditional NameN,N-dimethyl-L-histidine
CAS Registry NumberNot Available
SMILES
CN(C)[C@@H](CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C8H13N3O2/c1-11(2)7(8(12)13)3-6-4-9-5-10-6/h4-5,7H,3H2,1-2H3,(H,9,10)(H,12,13)/t7-/m0/s1
InChI KeyIMOBSLOLPCWZKQ-ZETCQYMHSA-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
    • 

  • Tertiary amine
    • 

  • Tertiary aliphatic amine
    • 

  • Amino acid
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Azacycle
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP-3.3ChemAxon
pKa (Strongest Acidic)1.37ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.13 m³·mol⁻¹ChemAxon
Polarizability18.35 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 ID389250  
KEGG Compound IDC04259  
BioCyc IDNALPHANALPHA-DIMETHYL-L-HISTIDINE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440274  
PDB IDNot Available
ChEBI ID16029  
Good Scents IDNot Available
References
General References
  1. Concha-Miranda M, Tang W, Hartmann K, Brecht M: Large-scale mapping of vocalization-related activity in the functionally diverse nuclei in rat posterior brainstem. J Neurosci. 2022 Sep 16. pii: JNEUROSCI.0813-22.2022. doi: 10.1523/JNEUROSCI.0813-22.2022. [PubMed:36113990  ] 
  2. Kausto J, Gluschkoff K, Turunen J, Selinheimo S, Peutere L, Vaananen A: Psychotherapy and change in mental health-related work disability: a prospective Finnish population-level register-based study with a quasi-experimental design. J Epidemiol Community Health. 2022 Sep 16. pii: jech-2022-218941. doi: 10.1136/jech-2022-218941. [PubMed:36113989  ] 
  3. Meulemans L, Baert Desurmont S, Waill MC, Castelain G, Killian A, Hauchard J, Frebourg T, Coulet F, Martins A, Muleris M, Gaildrat P: Comprehensive RNA and protein functional assessments contribute to the clinical interpretation of MSH2 variants causing in-frame splicing alterations. J Med Genet. 2022 Sep 16. pii: jmg-2022-108576. doi: 10.1136/jmg-2022-108576. [PubMed:36113988  ] 
  4. Otsuji S, Nishio Y, Tsujita M, Rio M, Huber C, Anton-Plagaro C, Mizuno S, Kawano Y, Miyatake S, Simon M, van Binsbergen E, van Jaarsveld RH, Matsumoto N, Cormier-Daire V, J Cullen P, Saitoh S, Kato K: Clinical diversity and molecular mechanism of VPS35L-associated Ritscher-Schinzel syndrome. J Med Genet. 2022 Sep 16. pii: jmg-2022-108602. doi: 10.1136/jmg-2022-108602. [PubMed:36113987  ] 
  5. Crul M, Breukels O: Safe handling of cytostatic drugs: recommendations from independent science. Eur J Hosp Pharm. 2022 Sep 16. pii: ejhpharm-2022-003469. doi: 10.1136/ejhpharm-2022-003469. [PubMed:36113986  ] 
  6. Kroshus E, Chrisman SPD, Glang A, Hunt T, Hays R, Lowry S, Peterson A, Garrett K, Ramshaw D, Hafferty K, Kinney E, Manzueta M, Steiner MK, Bollinger BJ, Chiampas G, Rivara FP: Concussion education for youth athletes using Pre-Game Safety Huddles: a cluster-randomised controlled trial. Inj Prev. 2022 Sep 16. pii: ip-2022-044665. doi: 10.1136/ip-2022-044665. [PubMed:36113984  ] 
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