NP-MRD: Showing NP-Card for (2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid (NP0259630)

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Record Information

Version

2.0

Created at

2022-09-08 01:33:56 UTC

Updated at

2022-09-08 01:33:56 UTC

NP-MRD ID

NP0259630

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid

Description

5-Bromo-N-methyl-l-tryptophan belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review very few articles have been published on 5-bromo-N-methyl-l-tryptophan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.3636    0.9106    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005    0.5887    1.2786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0547    0.3459    0.2853 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6992    0.3875    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4145    0.1940   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    0.1896   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757    0.0096   -1.8858 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567   -0.1069   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170   -0.2967   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473   -0.3693    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -0.2610    1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -0.3749    3.1807 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.0725    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.0064    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3391   -0.9775   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4914   -1.3795   -0.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -1.8500   -0.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    1.7804    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0302    0.0144    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268    1.1621   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7318    1.3358    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    1.1158   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -0.3474    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256    1.4097    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5212    0.3162   -2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285   -0.0375   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.3883   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -0.5170    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    0.0159    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2661   -2.8040   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  3 15  1  0
 15 17  1  0
 15 16  2  0
 14  5  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  6
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 17 30  1  0
M  END


  Mrv1652309082203332D          

 17 18  0  0  1  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 14  1  0  0  0  0
  8 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259630

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](CC1=CNC2=CC=C(Br)C=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H13BrN2O2/c1-14-11(12(16)17)4-7-6-15-10-3-2-8(13)5-9(7)10/h2-3,5-6,11,14-15H,4H2,1H3,(H,16,17)/t11-/m0/s1

> <INCHI_KEY>
JRDUELVJXRQKQH-NSHDSACASA-N

> <FORMULA>
C12H13BrN2O2

> <MOLECULAR_WEIGHT>
297.152

> <EXACT_MASS>
296.016041

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.41319275431427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-3-(5-bromo-1H-indol-3-yl)-2-(methylamino)propanoic acid

> <JCHEM_LOGP>
-0.09378246675554203

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.066274425605325

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.164308720520511

> <JCHEM_PKA_STRONGEST_BASIC>
10.640227592462209

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
68.60020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(5-bromo-1H-indol-3-yl)-2-(methylamino)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       7.591  -2.843   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    5    8                                                  
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₃BrN₂O₂

Average Mass

297.1520 Da

Monoisotopic Mass

296.01604 Da

IUPAC Name

(2S)-3-(5-bromo-1H-indol-3-yl)-2-(methylamino)propanoic acid

Traditional Name

(2S)-3-(5-bromo-1H-indol-3-yl)-2-(methylamino)propanoic acid

CAS Registry Number

Not Available

SMILES

CN[C@@H](CC1=CNC2=CC=C(Br)C=C12)C(O)=O

InChI Identifier

InChI=1S/C12H13BrN2O2/c1-14-11(12(16)17)4-7-6-15-10-3-2-8(13)5-9(7)10/h2-3,5-6,11,14-15H,4H2,1H3,(H,16,17)/t11-/m0/s1

InChI Key

JRDUELVJXRQKQH-NSHDSACASA-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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Aryl bromide
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Amino acid
Organoheterocyclic compound
Azacycle
Secondary amine
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organobromide
Organonitrogen compound
Organic oxide
Organooxygen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.094	ChemAxon
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	10.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.6 m³·mol⁻¹	ChemAxon
Polarizability	26.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10479242

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21776722

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid (NP0259630)

MOL for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

3D MOL for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

3D SDF for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

3D-SDF for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

PDB for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

3D PDB for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

SMILES for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

INCHI for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

Structure for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)

3D Structure for NP0259630 ((2s)-3-(5-bromo-1h-indol-3-yl)-2-(methylamino)propanoic acid)