NP-MRD: Showing NP-Card for (2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate (NP0171508)

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Record Information

Version

2.0

Created at

2022-09-03 08:03:20 UTC

Updated at

2022-09-03 08:03:21 UTC

NP-MRD ID

NP0171508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate

Description

CHEMBL2204075 belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on CHEMBL2204075.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    5.5784   -0.0749   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126   -0.0648   -0.7903 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.0407   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348    1.1567    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893    1.2264    0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832    2.9462    0.9402 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    0.0548    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6940    0.1034    1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    0.5488    0.6542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0861    0.5258    1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207   -0.1873    2.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192    1.2511    1.1921 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1169   -0.0904   -0.5722 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4142   -1.4813   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3526    0.5622   -1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1238    0.1894   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -1.1487    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049   -2.8323    1.0590 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -1.2083    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6289    0.0155   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3459    0.6471   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1187   -1.0736   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750    2.0637   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093    0.8731    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -0.8334    2.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943    1.6481    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3887   -1.6785   -1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -2.1057   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -1.8353    0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3394    1.6428   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3093    0.3988   -2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495    0.0275   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.2196   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760    0.2644   -2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -0.5819   -1.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928   -2.1285   -0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  7 17  1  0
 17 18  1  0
 17 19  2  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 19 36  1  0
M  CHG  2  12  -1  13   1
M  END


  Mrv1652309032210032D          

 19 19  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  3 19  1  0  0  0  0
M  CHG  2  12  -1  13   1
M  END
> <DATABASE_ID>
NP0171508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(Br)=C(C[C@H](C([O-])=O)[N+](C)(C)C)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H17Br2NO3/c1-16(2,3)12(13(17)18)7-9-10(14)5-8(19-4)6-11(9)15/h5-6,12H,7H2,1-4H3/t12-/m1/s1

> <INCHI_KEY>
HPWZPBRHLVYCSN-GFCCVEGCSA-N

> <FORMULA>
C13H17Br2NO3

> <MOLECULAR_WEIGHT>
395.091

> <EXACT_MASS>
392.957519

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.842585697747218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylazaniumyl)propanoate

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-0.8892592474717453

> <ALOGPS_LOGS>
-6.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8026281039471641

> <JCHEM_PKA_STRONGEST_BASIC>
-4.838152994631235

> <JCHEM_POLAR_SURFACE_AREA>
49.36

> <JCHEM_REFRACTIVITY>
103.6451

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6 Br   UNK     0       4.001  -0.770   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O-1
HETATM   13  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.771  -3.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.231  -0.976   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    7   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₇Br₂NO₃

Average Mass

395.0910 Da

Monoisotopic Mass

392.95752 Da

IUPAC Name

(2R)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylazaniumyl)propanoate

Traditional Name

(2R)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate

CAS Registry Number

Not Available

SMILES

COC1=CC(Br)=C(C[C@H](C([O-])=O)[N+](C)(C)C)C(Br)=C1

InChI Identifier

InChI=1S/C13H17Br2NO3/c1-16(2,3)12(13(17)18)7-9-10(14)5-8(19-4)6-11(9)15/h5-6,12H,7H2,1-4H3/t12-/m1/s1

InChI Key

HPWZPBRHLVYCSN-GFCCVEGCSA-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 phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
D-alpha-amino acid
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Bromobenzene
Halobenzene
Aralkylamine
Benzenoid
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Organic oxygen compound
Organic salt
Amine
Organohalogen compound
Carbonyl group
Organic nitrogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	-0.48	ALOGPS
logP	-0.89	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	0.8	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	103.65 m³·mol⁻¹	ChemAxon
Polarizability	31.84 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

28650782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71459445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate (NP0171508)

MOL for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

3D MOL for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

3D SDF for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

3D-SDF for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

PDB for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

3D PDB for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

SMILES for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

INCHI for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

Structure for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)

3D Structure for NP0171508 ((2r)-3-(2,6-dibromo-4-methoxyphenyl)-2-(trimethylammonio)propanoate)