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

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Record Information

Version

2.0

Created at

2022-09-09 17:40:36 UTC

Updated at

2022-09-09 17:40:36 UTC

NP-MRD ID

NP0288101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n,n-dimethyl-l-histidine

Description

N(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. n,n-dimethyl-l-histidine was first documented in 1970 (PMID: 5438052). Based on a literature review very few articles have been published on N(alpha),N(alpha)-dimethyl-L-histidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

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

View in JSmol

Synonyms

Value	Source
Nalpha,nalpha-dimethyl-L-histidine	ChEBI
N(a),N(a)-Dimethyl-L-histidine	Generator
N(Α),N(α)-dimethyl-L-histidine	Generator

Chemical Formula

C₈H₁₃N₃O₂

Average Mass

183.2110 Da

Monoisotopic Mass

183.10078 Da

IUPAC Name

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

Traditional Name

N,N-dimethyl-L-histidine

CAS Registry Number

Not 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 Key

IMOBSLOLPCWZKQ-ZETCQYMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

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
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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

N(alpha)-methyl-L-histidines (CHEBI:16029 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	1.37	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.13 m³·mol⁻¹	ChemAxon
Polarizability	18.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389250

KEGG Compound ID

C04259

BioCyc ID

NALPHANALPHA-DIMETHYL-L-HISTIDINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440274

PDB ID

Not Available

ChEBI ID

16029

Good Scents ID

Not Available

References

General References

Reinhold VN, Ishikawa Y, Melville DB: Conversion of histidine to hercynine by Neurospora crassa. J Bacteriol. 1970 Mar;101(3):881-4. doi: 10.1128/jb.101.3.881-884.1970. [PubMed:5438052 ]
LOTUS database [Link]

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

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

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

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

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

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

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

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

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

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

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