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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-06-04 21:36:08 UTC

Update Date

2022-09-22 17:44:16 UTC

HMDB ID

HMDB0240660

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Bromotryptophan

Description

5-Bromotryptophan, also known as 5-BRTRP, 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 a small amount of articles have been published on 5-Bromotryptophan.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0240660

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0240660
HETATM    1  N1  UNL     1       3.595  -0.116   0.588  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.295  -0.484   0.003  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.332  -0.652   1.140  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.032  -0.987   0.725  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.572  -2.247   0.547  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.838  -2.122   0.108  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.140  -0.805  -0.006  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.275  -0.159  -0.386  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.348   1.236  -0.400  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.226   1.934  -0.013  1.00  0.00           C  
HETATM   11 BR1  UNL     1      -2.251   3.841  -0.000  1.00  0.00          BR  
HETATM   12  C9  UNL     1      -1.083   1.280   0.369  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.041  -0.100   0.370  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.904   0.546  -0.943  1.00  0.00           C  
HETATM   15  O1  UNL     1       0.982   0.354  -1.774  1.00  0.00           O  
HETATM   16  O2  UNL     1       2.544   1.787  -0.955  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.634  -0.452   1.585  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.723   0.919   0.570  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.443  -1.452  -0.543  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.763  -1.385   1.871  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.296   0.331   1.691  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.032  -3.177   0.743  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.484  -2.905  -0.112  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.179  -0.708  -0.697  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.263   1.727  -0.708  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.225   1.876   0.665  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.481   1.921  -1.253  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   10   25
CONECT   10   11   12
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
(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
L-5-Bromotryptophan	HMDB
5-Bromotryptophan, (L)-isomer	MeSH
5-BRTRP	MeSH
5-Bromotryptophan	HMDB

Chemical Formula

C₁₁H₁₁BrN₂O₂

Average Molecular Weight

283.125

Monoisotopic Molecular Weight

282.000391

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

25197-99-3

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31396400)

Source

Exogenous

Exogenous (HMDB: HMDB0240660)

Process

Not Available

Role

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)	1.51	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	182.343	30932474
DeepCCS	[M+Na]+	157.8	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.17 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0217 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1040.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.7 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	285.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	298.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	709.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	321.0 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	1027.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	161.0 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	146.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Bromotryptophan	N[C@@H](CC1=CNC2=CC=C(Br)C=C12)C(O)=O	3496.8	Standard polar	33892256
5-Bromotryptophan	N[C@@H](CC1=CNC2=CC=C(Br)C=C12)C(O)=O	2280.0	Standard non polar	33892256
5-Bromotryptophan	N[C@@H](CC1=CNC2=CC=C(Br)C=C12)C(O)=O	2720.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Bromotryptophan,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(Br)C=C12	2457.7	Semi standard non polar	33892256
5-Bromotryptophan,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O	2496.7	Semi standard non polar	33892256
5-Bromotryptophan,1TMS,isomer #3	C[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(Br)=CC=C21	2537.2	Semi standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2457.4	Semi standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2341.4	Standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2910.6	Standard polar	33892256
5-Bromotryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12	2458.9	Semi standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12	2346.5	Standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12	3042.5	Standard polar	33892256
5-Bromotryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	2626.6	Semi standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	2432.2	Standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	3107.3	Standard polar	33892256
5-Bromotryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	2493.1	Semi standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	2371.7	Standard non polar	33892256
5-Bromotryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	3044.1	Standard polar	33892256
5-Bromotryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2598.8	Semi standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2478.8	Standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2764.0	Standard polar	33892256
5-Bromotryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2461.4	Semi standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2409.6	Standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C	2699.9	Standard polar	33892256
5-Bromotryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	2643.9	Semi standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	2514.3	Standard non polar	33892256
5-Bromotryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C	2842.2	Standard polar	33892256
5-Bromotryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2649.2	Semi standard non polar	33892256
5-Bromotryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2554.4	Standard non polar	33892256
5-Bromotryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2620.2	Standard polar	33892256
5-Bromotryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(Br)C=C12	2737.7	Semi standard non polar	33892256
5-Bromotryptophan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O	2778.0	Semi standard non polar	33892256
5-Bromotryptophan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(Br)=CC=C21	2785.4	Semi standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2944.3	Semi standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2791.9	Standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3041.4	Standard polar	33892256
5-Bromotryptophan,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=C(Br)C=C12	2921.5	Semi standard non polar	33892256
5-Bromotryptophan,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=C(Br)C=C12	2749.8	Standard non polar	33892256
5-Bromotryptophan,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=C(Br)C=C12	3120.3	Standard polar	33892256
5-Bromotryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3120.6	Semi standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2839.1	Standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3139.0	Standard polar	33892256
5-Bromotryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	2959.6	Semi standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	2795.4	Standard non polar	33892256
5-Bromotryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O	3123.5	Standard polar	33892256
5-Bromotryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3309.9	Semi standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3071.9	Standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3012.5	Standard polar	33892256
5-Bromotryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3077.8	Semi standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2999.6	Standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2982.0	Standard polar	33892256
5-Bromotryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3298.3	Semi standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3047.2	Standard non polar	33892256
5-Bromotryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3053.2	Standard polar	33892256
5-Bromotryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3459.7	Semi standard non polar	33892256
5-Bromotryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3232.9	Standard non polar	33892256
5-Bromotryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(Br)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2970.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Bromotryptophan 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 - 5-Bromotryptophan 10V, Negative-QTOF	splash10-01sl-4390000000-2566b4bf060172a0573f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Bromotryptophan 20V, Negative-QTOF	splash10-002f-7940000000-b706354445057c518b40	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Bromotryptophan 40V, Negative-QTOF	splash10-004i-9130000000-8d05dcffcda6fa067b76	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Bromotryptophan 10V, Positive-QTOF	splash10-014i-0090000000-7fec889b670786a6152c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Bromotryptophan 20V, Positive-QTOF	splash10-014i-0090000000-5f0c320616d69f2c20b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Bromotryptophan 40V, Positive-QTOF	splash10-069r-0980000000-251e274a31428539da8f	2021-09-22	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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31396400	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

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

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

Zarei I, Oppel RC, Borresen EC, Brown RJ, Ryan EP: Modulation of plasma and urine metabolome in colorectal cancer survivors consuming rice bran. Integr Food Nutr Metab. 2019 May;6(3). doi: 10.15761/IFNM.1000252. Epub 2019 Apr 5. [PubMed:31396400 ]

Showing metabocard for 5-Bromotryptophan (HMDB0240660)

MOL for HMDB0240660 (5-Bromotryptophan)

3D MOL for HMDB0240660 (5-Bromotryptophan)

3D SDF for HMDB0240660 (5-Bromotryptophan)

3D-SDF for HMDB0240660 (5-Bromotryptophan)

PDB for HMDB0240660 (5-Bromotryptophan)

3D PDB for HMDB0240660 (5-Bromotryptophan)

SMILES for HMDB0240660 (5-Bromotryptophan)

INCHI for HMDB0240660 (5-Bromotryptophan)

Structure for HMDB0240660 (5-Bromotryptophan)

3D Structure for HMDB0240660 (5-Bromotryptophan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra