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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-08-27 20:04:30 UTC

Update Date

2021-09-14 15:29:55 UTC

HMDB ID

HMDB0242168

Secondary Accession Numbers

None

Metabolite Identification

Common Name

6-Bromo-L-tryptophan

Description

6-Bromo-L-tryptophan 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. Based on a literature review very few articles have been published on 6-Bromo-L-tryptophan.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05041401102D          

 17 18  0  0  1  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.4230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    3.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.6492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
  9 13  1  1  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
  9 17  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0242168

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](N)(CC1=CNC2=C1C=CC(Br)=C2)C(O)=O

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

> <INCHI_KEY>
OAORYCZPERQARS-VIFPVBQESA-N

> <FORMULA>
C11H11BrN2O2

> <MOLECULAR_WEIGHT>
283.121

> <EXACT_MASS>
282.000390253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.788168320503907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-(6-bromo-1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-0.31749243835940333

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.88322779944398

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5253885462009942

> <JCHEM_PKA_STRONGEST_BASIC>
9.395489296594373

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
63.825599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-6'-bromotryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    6   14                                                       
CONECT    6    3    5    8                                                  
CONECT    7    1    4   12                                                  
CONECT    8    2    6   10                                                  
CONECT    9    3   11   13   17                                             
CONECT   10    4    8   14                                                  
CONECT   11    9   15   16                                                  
CONECT   12    7                                                            
CONECT   13    9                                                            
CONECT   14    5   10                                                       
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0242168
HETATM    1  N1  UNL     1      -2.869  -2.101  -0.792  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.919  -1.244  -0.186  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.287  -0.383  -1.274  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.277   0.542  -0.706  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.406   1.882  -0.486  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.722   2.386   0.041  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.590   1.382   0.166  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.869   1.304   0.633  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.586   0.129   0.669  1.00  0.00           C  
HETATM   10 BR1  UNL     1       5.367   0.057   1.325  1.00  0.00          BR  
HETATM   11  C8  UNL     1       2.982  -1.029   0.209  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.690  -0.982  -0.269  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.008   0.216  -0.287  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.609  -0.419   0.835  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.807  -0.458   1.119  1.00  0.00           O  
HETATM   16  O2  UNL     1      -1.796   0.490   1.534  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.597  -2.632  -1.607  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.842  -2.027  -0.522  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.069  -1.769   0.302  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.065   0.154  -1.840  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.809  -1.092  -1.982  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.292   2.475  -0.702  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.855   3.388   0.293  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.382   2.189   1.003  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.523  -1.972   0.225  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.209  -1.897  -0.633  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.137   1.411   1.792  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5    5   13
CONECT    5    6   22
CONECT    6    7   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   11   11
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   14   15   15   16
CONECT   16   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid	ChEBI
(S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoate	Generator
6-Bromotryptophan	HMDB
6-BR-Tryptophan	HMDB

Chemical Formula

C₁₁H₁₁BrN₂O₂

Average Molecular Weight

283.121

Monoisotopic Molecular Weight

282.000390253

IUPAC Name

(2S)-2-amino-3-(6-bromo-1H-indol-3-yl)propanoic acid

Traditional Name

L-6'-bromotryptophan

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC1=CNC2=C1C=CC(Br)=C2)C(O)=O

InChI Identifier

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

InChI Key

OAORYCZPERQARS-VIFPVBQESA-N

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

non-proteinogenic L-alpha-amino acid (CHEBI:47276 )
bromoamino acid (CHEBI:47276 )
L-tryptophan derivative (CHEBI:47276 )
bromoindole (CHEBI:47276 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.42	ALOGPS
logP	-0.32	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	9.4	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	24.79 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	151.952	30932474
DeepCCS	[M-H]-	149.557	30932474
DeepCCS	[M-2H]-	182.713	30932474
DeepCCS	[M+Na]+	157.957	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.1666 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1079.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	327.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	320.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	289.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	282.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	718.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	332.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1049.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	136.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	136.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Bromo-L-tryptophan	[H][C@](N)(CC1=CNC2=C1C=CC(Br)=C2)C(O)=O	3475.9	Standard polar	33892256
6-Bromo-L-tryptophan	[H][C@](N)(CC1=CNC2=C1C=CC(Br)=C2)C(O)=O	2304.8	Standard non polar	33892256
6-Bromo-L-tryptophan	[H][C@](N)(CC1=CNC2=C1C=CC(Br)=C2)C(O)=O	2699.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Bromo-L-tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2481.3	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2333.5	Standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2908.6	Standard polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12	2470.8	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12	2313.5	Standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12	3032.7	Standard polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	2646.7	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	2425.0	Standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	3108.6	Standard polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	2502.4	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	2335.5	Standard non polar	33892256
6-Bromo-L-tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	3032.3	Standard polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2625.6	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2477.8	Standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2760.9	Standard polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2471.9	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2377.1	Standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C	2695.0	Standard polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	2658.2	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	2482.8	Standard non polar	33892256
6-Bromo-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C	2836.2	Standard polar	33892256
6-Bromo-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2673.7	Semi standard non polar	33892256
6-Bromo-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2526.6	Standard non polar	33892256
6-Bromo-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2612.6	Standard polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2949.4	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2794.2	Standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3043.7	Standard polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12	2943.0	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12	2717.6	Standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12	3113.2	Standard polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3152.0	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2837.7	Standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3137.2	Standard polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	2987.1	Semi standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	2754.2	Standard non polar	33892256
6-Bromo-L-tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O	3116.9	Standard polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3315.8	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3084.8	Standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3011.0	Standard polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3102.4	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2961.0	Standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2977.8	Standard polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3319.1	Semi standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3004.9	Standard non polar	33892256
6-Bromo-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3047.7	Standard polar	33892256
6-Bromo-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3485.7	Semi standard non polar	33892256
6-Bromo-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3196.6	Standard non polar	33892256
6-Bromo-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(Br)=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2962.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Bromo-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bu-8190000000-ec90f8808efdddfad91b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Bromo-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 10V, Positive-QTOF	splash10-015i-0090000000-92b764dff09b9a388356	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 20V, Positive-QTOF	splash10-014i-0090000000-506c5f5df9db3d9cf08f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 40V, Positive-QTOF	splash10-0avi-0290000000-afd645ea4a1d99bd99a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 10V, Negative-QTOF	splash10-0006-0970000000-a80fdb9b6fa30f81f92e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 20V, Negative-QTOF	splash10-0006-4900000000-1c621a2777280ccf4159	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Bromo-L-tryptophan 40V, Negative-QTOF	splash10-0006-7940000000-c6d1fb4ca487fa4f0806	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8032696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9856996

PDB ID

Not Available

ChEBI ID

47276

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kong SW, Hernandez-Ferrer C: Assessment of coverage for endogenous metabolites and exogenous chemical compounds using an untargeted metabolomics platform. Pac Symp Biocomput. 2020;25:587-598. [PubMed:31797630 ]

Showing metabocard for 6-Bromo-L-tryptophan (HMDB0242168)

MOL for HMDB0242168 (6-Bromo-L-tryptophan)

3D MOL for HMDB0242168 (6-Bromo-L-tryptophan)

3D SDF for HMDB0242168 (6-Bromo-L-tryptophan)

3D-SDF for HMDB0242168 (6-Bromo-L-tryptophan)

PDB for HMDB0242168 (6-Bromo-L-tryptophan)

3D PDB for HMDB0242168 (6-Bromo-L-tryptophan)

SMILES for HMDB0242168 (6-Bromo-L-tryptophan)

INCHI for HMDB0242168 (6-Bromo-L-tryptophan)

Structure for HMDB0242168 (6-Bromo-L-tryptophan)

3D Structure for HMDB0242168 (6-Bromo-L-tryptophan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra