NP-MRD: Showing NP-Card for L-Histidine trimethylbetaine (NP0045363)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:39 UTC

Updated at

2022-03-17 19:18:39 UTC

NP-MRD ID

NP0045363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Histidine trimethylbetaine

Description

L-Histidine trimethylbetaine, also known as hercynine, 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. L-Histidine trimethylbetaine is a very strong basic compound (based on its pKa). Outside of the human body, L-Histidine trimethylbetaine has been detected, but not quantified in, several different foods, such as wild rices, corns, triticales, millets, and red rices. L-Histidine trimethylbetaine is found in Apis cerana. This could make L-histidine trimethylbetaine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -0.5394   -1.2333   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921   -0.0542   -0.3357 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.4747   -0.5012    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844    0.7427   -1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5106    0.7035    0.6571 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7944    0.2357    1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9099    0.1288    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.4569   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    0.1427   -1.4782 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9377   -0.3753   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -0.3845    0.6041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028    0.8541    1.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.5835    1.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898    0.1336    2.9930 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3208   -2.0521   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2674   -1.6254   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228   -1.0945   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233   -1.3324   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720   -0.8242    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2247    0.3045    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.4517   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761    0.5235   -2.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    1.8059   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    1.7824    0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.7429    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    0.9408    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    0.8930   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746   -0.7204   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -0.7429    1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  5 12  1  0
 12 14  1  0
 12 13  2  0
 11  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  6
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
M  CHG  2   2   1  14  -1
M  END


  Mrv0541 02241217362D          

 14 14  0  0  0  0            999 V2000
   -1.6092   -0.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -1.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    0.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    0.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1960    0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    1.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138    1.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    1.5682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145   -1.8155    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1138   -0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362   -1.1557    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2066   -1.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1960   -1.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  CHG  2  10  -1  12   1
M  END
> <DATABASE_ID>
NP0045363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)C(CC1=CN=CN1)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)

> <INCHI_KEY>
GPPYTCRVKHULJH-UHFFFAOYSA-N

> <FORMULA>
C9H15N3O2

> <MOLECULAR_WEIGHT>
197.2343

> <EXACT_MASS>
197.116426739

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.179131001211132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate

> <ALOGPS_LOGP>
-1.78

> <JCHEM_LOGP>
-4.51732507242313

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.822982942245382

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.025270364061525

> <JCHEM_PKA_STRONGEST_BASIC>
6.7044239385636715

> <JCHEM_POLAR_SURFACE_AREA>
68.81

> <JCHEM_REFRACTIVITY>
74.87899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3H-imidazol-4-yl)-2-(trimethylammonio)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.004  -1.077   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.772  -2.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.386  -1.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.386   0.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.693   1.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.233   1.077   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.004   2.311   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.079   3.544   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.693   2.927   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -2.080  -3.389   0.000  0.00  0.00           O-1
HETATM   11  C   UNK     0       2.079  -1.077   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.001  -2.157   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0       0.386  -3.544   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.233  -2.927   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    2                                                            
CONECT   11   12                                                            
CONECT   12    3   11   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Hercynine	HMDB
Nalpha,nalpha,nalpha-trimethyl-L-histidine	HMDB
3-(1H-Imidazol-5-yl)-2-(trimethylazaniumyl)propanoic acid	Generator

Chemical Formula

C₉H₁₅N₃O₂

Average Mass

197.2343 Da

Monoisotopic Mass

197.11643 Da

IUPAC Name

3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate

Traditional Name

3-(3H-imidazol-4-yl)-2-(trimethylammonio)propanoate

CAS Registry Number

534-30-5

SMILES

C[N+](C)(C)C(CC1=CN=CN1)C([O-])=O

InChI Identifier

InChI=1S/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)

InChI Key

GPPYTCRVKHULJH-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Apis cerana	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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
Imidazolyl carboxylic acid derivative
Aralkylamine
Azole
Tetraalkylammonium salt
Imidazole
Heteroaromatic compound
Quaternary ammonium salt
Carboxylic acid salt
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (NALPHANALPHANALPHA-TRIMETHYL-L-H )

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	-1.8	ALOGPS
logP	-4.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.88 m³·mol⁻¹	ChemAxon
Polarizability	20.18 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

HMDB0029422

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000520

KNApSAcK ID

Not Available

Chemspider ID

2340795

KEGG Compound ID

C05575

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083620

PDB ID

Not Available

ChEBI ID

15781

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for L-Histidine trimethylbetaine (NP0045363)

MOL for NP0045363 (L-Histidine trimethylbetaine)

3D MOL for NP0045363 (L-Histidine trimethylbetaine)

3D SDF for NP0045363 (L-Histidine trimethylbetaine)

3D-SDF for NP0045363 (L-Histidine trimethylbetaine)

PDB for NP0045363 (L-Histidine trimethylbetaine)

3D PDB for NP0045363 (L-Histidine trimethylbetaine)

SMILES for NP0045363 (L-Histidine trimethylbetaine)

INCHI for NP0045363 (L-Histidine trimethylbetaine)

Structure for NP0045363 (L-Histidine trimethylbetaine)

3D Structure for NP0045363 (L-Histidine trimethylbetaine)