NP-MRD: Showing NP-Card for 2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid (NP0247007)

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Record Information

Version

2.0

Created at

2022-09-07 08:40:00 UTC

Updated at

2022-09-07 08:40:00 UTC

NP-MRD ID

NP0247007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid

Description

2-Amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid 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. 2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid is found in Rhodomela confervoides. 2-Amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261501262D          

 16 16  0  0  0  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
    2.1434    1.2375    0.0000 O   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
    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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  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  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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Br  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(CC(N)C(O)=O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C10H12BrNO4/c1-16-9-6(11)2-5(4-8(9)13)3-7(12)10(14)15/h2,4,7,13H,3,12H2,1H3,(H,14,15)

> <INCHI_KEY>
UGJKNPLWDTUBEB-UHFFFAOYSA-N

> <FORMULA>
C10H12BrNO4

> <MOLECULAR_WEIGHT>
290.113

> <EXACT_MASS>
288.994971

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.35592295474207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-1.34

> <JCHEM_LOGP>
-0.8774994999517467

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.037609165976004

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9060945475846207

> <JCHEM_PKA_STRONGEST_BASIC>
9.67412328333455

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
61.1832

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         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  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+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  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoate	Generator

Chemical Formula

C₁₀H₁₂BrNO₄

Average Mass

290.1130 Da

Monoisotopic Mass

288.99497 Da

IUPAC Name

2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid

Traditional Name

2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(CC(N)C(O)=O)C=C1Br

InChI Identifier

InChI=1S/C10H12BrNO4/c1-16-9-6(11)2-5(4-8(9)13)3-7(12)10(14)15/h2,4,7,13H,3,12H2,1H3,(H,14,15)

InChI Key

UGJKNPLWDTUBEB-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, 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

Species Name	Source	Reference
Rhodomela confervoides	LOTUS Database	35616633

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
Methoxyphenol
Phenoxy compound
Anisole
3-halophenol
3-bromophenol
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Phenol
Aralkylamine
Benzenoid
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Organobromide
Amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organohalogen compound
Primary amine
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	-1.3	ALOGPS
logP	-0.88	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	0.91	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.18 m³·mol⁻¹	ChemAxon
Polarizability	24.36 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90836506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid (NP0247007)

MOL for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

3D MOL for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

3D SDF for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

3D-SDF for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

PDB for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

3D PDB for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

SMILES for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

INCHI for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

Structure for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)

3D Structure for NP0247007 (2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl)propanoic acid)