NP-MRD: Showing NP-Card for (2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid (NP0195797)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 13:43:56 UTC

Updated at

2022-09-04 13:43:57 UTC

NP-MRD ID

NP0195797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5-Bromotryptophan (CAS: 6548-09-0) Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. 5-Bromotryptophan has been identified in blood (PMID: 31396400 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306042023202D          

 16 17  0  0  0  0            999 V2000
10001.766210000.0195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4806 9999.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.766210000.8454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.197010000.0195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4806 9998.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.444210001.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.337510000.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.251210000.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2670 9997.9422    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 9999.031810000.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.224910000.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9699 9999.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5219 9998.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3289 9998.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5838 9999.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0520 9999.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  7  8  2  0  0  0  0
  6  8  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 13  9  1  0  0  0  0
  6 10  1  0  0  0  0
 15  7  1  0  0  0  0
  7 16  1  0  0  0  0
 16  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195797

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H11BrN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1

> <INCHI_KEY>
KZDNJQUJBMDHJW-VIFPVBQESA-N

> <FORMULA>
C11H11BrN2O2

> <MOLECULAR_WEIGHT>
283.125

> <EXACT_MASS>
282.000391

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.544355342904844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-0.31749133988394007

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.066378065099467

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5102474013992309

> <JCHEM_PKA_STRONGEST_BASIC>
9.393292829943487

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
63.82560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-20         0                                  
HETATM    1  C   UNK     0    8669.9648666.703   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.2978665.933   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8669.9648668.245   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8672.6348666.703   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8671.2978664.392   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8665.6298668.555   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8667.2978666.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.1368668.234   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0    8663.4328662.825   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0    8664.8598667.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3538666.901   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.8778665.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.9088664.292   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.4148664.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.8908666.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6308665.933   0.000  0.00  0.00           C+0
CONECT    1    2    3   16                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    8   10                                                       
CONECT    7    8   15   16                                                  
CONECT    8    7    6                                                       
CONECT    9   13                                                            
CONECT   10   11   15    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    9                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10    7                                                  
CONECT   16    7    1                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-3-(5-bromo-1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Amino-3-(5-bromo-1H-indol-3-yl)propionic acid	HMDB
(S)-2-Amino-3-(5-bromo-1H-indol-3-yl)propanoic acid	HMDB
(S)-2-Amino-3-(5-bromo-1H-indol-3-yl)propanoicacid	HMDB
(S)-2-Amino-3-(5-bromo-1H-indol-3-yl)propionic acid	HMDB
2-Amino-3-(5-bromo-1H-indol-3-yl)propanoic acid	HMDB
2-Amino-3-(5-bromo-1H-indol-3-yl)propionic acid	HMDB
5-Bromo-L-tryptophan	HMDB
5-Bromotryptophan	HMDB
L-5-Bromotryptophan	HMDB

Chemical Formula

C₁₁H₁₁BrN₂O₂

Average Mass

283.1250 Da

Monoisotopic Mass

282.00039 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H11BrN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1

InChI Key

KZDNJQUJBMDHJW-VIFPVBQESA-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 indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Aryl bromide
Aryl halide
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Primary aliphatic amine
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen 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	-0.42	ALOGPS
logP	-0.32	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.83 m³·mol⁻¹	ChemAxon
Polarizability	24.54 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

HMDB0240660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

559338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

644329

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid (NP0195797)

MOL for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

3D MOL for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

3D SDF for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

3D-SDF for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

PDB for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

3D PDB for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

SMILES for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

INCHI for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

Structure for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)

3D Structure for NP0195797 ((2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid)