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Showing NP-Card for 3-Bromotyrosine (NP0334745)

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Record Information
Version2.0
Created at2024-09-10 19:47:00 UTC
Updated at2024-09-10 19:47:00 UTC
NP-MRD IDNP0334745
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Bromotyrosine
Description3-Bromotyrosine belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3-Bromotyrosine was first documented in 2010 (PMID: 20647044). Based on a literature review a significant number of articles have been published on 3-Bromotyrosine (PMID: 39248167) (PMID: 39208650) (PMID: 38074145) (PMID: 37685068) (PMID: 36126269) (PMID: 34439416).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334745 (3-Bromotyrosine)


  Mrv2104 05252322192D          

 14 14  0  0  0  0            999 V2000
   13.4871   -8.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4871   -9.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726   -8.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726  -10.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0581   -8.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0581   -9.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3436  -10.1187    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.7726  -10.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726   -7.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4870   -7.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4870   -6.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015   -5.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7725   -5.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015   -7.6437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
M  END
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3D MOL for NP0334745 (3-Bromotyrosine)

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3D SDF for NP0334745 (3-Bromotyrosine)

  Mrv2104 05252322192D          

 14 14  0  0  0  0            999 V2000
   13.4871   -8.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4871   -9.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726   -8.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726  -10.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0581   -8.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0581   -9.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3436  -10.1187    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.7726  -10.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7726   -7.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4870   -7.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4870   -6.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015   -5.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7725   -5.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015   -7.6437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC=C(O)C(Br)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C9H10BrNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)

> <INCHI_KEY>
HGWOSUKIFQMEIF-UHFFFAOYNA-N

> <FORMULA>
C9H10BrNO3

> <MOLECULAR_WEIGHT>
260.087

> <EXACT_MASS>
258.984406

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.541146419206175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid

> <JCHEM_LOGP>
-0.7201337661150635

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.09937635149683

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9920207480025627

> <JCHEM_PKA_STRONGEST_BASIC>
9.479921857889027

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
54.72

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-tyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334745 (3-Bromotyrosine)
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PDB for NP0334745 (3-Bromotyrosine)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      25.176 -16.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.176 -18.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.842 -15.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.842 -18.888   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.508 -16.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.508 -18.118   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      21.175 -18.888   0.000  0.00  0.00          Br+0
HETATM    8  O   UNK     0      23.842 -20.428   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      23.842 -14.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.176 -13.498   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.176 -11.958   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      26.509 -11.188   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.842 -11.188   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      26.509 -14.268   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    9                                                  
CONECT    4    2    6    8                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0334745 (3-Bromotyrosine)
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SMILES for NP0334745 (3-Bromotyrosine)
NC(CC1=CC=C(O)C(Br)=C1)C(O)=O
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INCHI for NP0334745 (3-Bromotyrosine)
InChI=1/C9H10BrNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H10BrNO3
Average Mass260.0870 Da
Monoisotopic Mass258.98441 Da
IUPAC Name2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid
Traditional Name3-bromo-tyrosine
CAS Registry NumberNot Available
SMILES
NC(CC1=CC=C(O)C(Br)=C1)C(O)=O
InChI Identifier
InChI=1/C9H10BrNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)
InChI KeyHGWOSUKIFQMEIF-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentTyrosine and derivatives  
Alternative Parents
Substituents
  • Tyrosine or derivatives
    • 

  • Phenylalanine or derivatives
    • 

  • 3-phenylpropanoic-acid
    • 

  • Alpha-amino acid
    • 

  • Amphetamine or derivatives
    • 

  • 2-bromophenol
    • 

  • 2-halophenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Halobenzene
    • 

  • Phenol
    • 

  • Bromobenzene
    • 

  • Aralkylamine
    • 

  • Aryl halide
    • 

  • Aryl bromide
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organohalogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organobromide
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.72ChemAxon
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.72 m³·mol⁻¹ChemAxon
Polarizability21.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Thomas ME, Markowitz JE, Arwood AC, Germany JM, Gilliland WM Jr: An LC-MS/MS method for the quantification of 3-bromotyrosine in plasma from patients diagnosed with eosinophilic esophagitis. Anal Methods. 2024 Oct 3;16(38):6509-6516. doi: 10.1039/d4ay00697f. [PubMed:39248167  ] 
  2. Moriya RG, Parthiban A, Devi N, Jorvekar SB, Baruah RS, Biswas B, Saharia N, Rao S, Bankar JS, Prasad SK, Sudhagar S, Murty US, Borkar RM: Comprehensive assessment of Zingiber sianginensis: Phytometabolomic analysis and its impact on oxidative stress biomarkers. J Pharm Biomed Anal. 2024 Dec 15;251:116421. doi: 10.1016/j.jpba.2024.116421.  Epub 2024 Aug 15. [PubMed:39208650  ] 
  3. Wan X, Zhou Q, Chen H, Li Z, Mo M, Liu Z, Zhang H, He Z, Xiao G, Zheng Y, Lin H, Ren D: Astragaloside IV improves slow transit constipation by regulating gut microbiota and enterochromaffin cells. Front Pharmacol. 2023 Nov 21;14:1196210. doi: 10.3389/fphar.2023.1196210.  eCollection 2023. [PubMed:38074145  ] 
  4. Sattasathuchana P, Thengchaisri N, Minamoto Y, Minamoto T, Lidbury JA, Suchodolski JS, Steiner JM: Serum and Fecal 3-Bromotyrosine Concentrations in Dogs with Chronic Inflammatory Enteropathy: Clinical Parameters and Histopathological Changes. Animals (Basel). 2023 Sep 4;13(17):2804. doi: 10.3390/ani13172804. [PubMed:37685068  ] 
  5. Wang Z, Xu W, Comhair SAA, Fu X, Shao Z, Bearden R, Zein JG, Bleecker ER, Castro M, Denlinger LC, Fahy JV, Israel E, Levy BD, Jarjour NN, Moore WC, Wenzel SE, Mauger DT, Gaston B, Hazen SL, Erzurum SC: Urinary total conjugated 3-bromotyrosine, asthma severity, and exacerbation risk. Am J Physiol Lung Cell Mol Physiol. 2022 Nov 1;323(5):L548-L557. doi:  10.1152/ajplung.00141.2022. Epub 2022 Sep 20. [PubMed:36126269  ] 
  6. Trocha M, Fleszar MG, Fortuna P, Lewandowski L, Gostomska-Pampuch K, Sozanski T, Merwid-Lad A, Krzystek-Korpacka M: Sitagliptin Modulates Oxidative, Nitrative and Halogenative Stress and Inflammatory Response in Rat Model of Hepatic Ischemia-Reperfusion. Antioxidants (Basel). 2021 Jul 22;10(8):1168. doi: 10.3390/antiox10081168. [PubMed:34439416  ] 
  7. Paumann-Page M, Kienzl NF, Motwani J, Bathish B, Paton LN, Magon NJ, Sevcnikar B, Furtmuller PG, Traxlmayr MW, Obinger C, Eccles MR, Winterbourn CC: Peroxidasin protein expression and enzymatic activity in metastatic melanoma cell lines are associated with invasive potential. Redox Biol. 2021 Oct;46:102090. doi: 10.1016/j.redox.2021.102090. Epub 2021 Aug  4. [PubMed:34438259  ] 
  8. Bathish B, Paumann-Page M, Paton LN, Kettle AJ, Winterbourn CC: Peroxidasin mediates bromination of tyrosine residues in the extracellular matrix. J Biol Chem. 2020 Sep 4;295(36):12697-12705. doi: 10.1074/jbc.RA120.014504. Epub  2020 Jul 16. [PubMed:32675287  ] 
  9. Di Stefano A, Maniscalco M, Balbi B, Ricciardolo FLM: Oxidative and Nitrosative Stress in the Pathogenesis of Obstructive Lung Diseases of Increasing Severity. Curr Med Chem. 2020;27(42):7149-7158. doi: 10.2174/0929867327666200604165451. [PubMed:32496983  ] 
  10. Sattasathuchana P, Thengchaisri N, Suchodolski JS, Lidbury JA, Steiner JM: Analytical validation of fecal 3-bromotyrosine concentrations in healthy dogs and dogs with chronic enteropathy. J Vet Diagn Invest. 2019 May;31(3):434-439. doi: 10.1177/1040638719831340. Epub  2019 Feb 15. [PubMed:30767618  ] 
  11. Comhair SAA, Bochenek G, Baicker-McKee S, Wang Z, Stachura T, Sanak M, Hammel JP, Hazen SL, Erzurum SC, Nizankowska-Mogilnicka E: The utility of biomarkers in diagnosis of aspirin exacerbated respiratory disease. Respir Res. 2018 Oct 30;19(1):210. doi: 10.1186/s12931-018-0909-6. [PubMed:30376852  ] 
  12. Heilmann RM, Steiner JM: Clinical utility of currently available biomarkers in inflammatory enteropathies of dogs. J Vet Intern Med. 2018 Sep;32(5):1495-1508. doi: 10.1111/jvim.15247. Epub 2018  Sep 17. [PubMed:30222209  ] 
  13. Weaver JB, Boxer SG: Genetic Code Expansion in Rhodobacter sphaeroides to Incorporate Noncanonical Amino Acids into Photosynthetic Reaction Centers. ACS Synth Biol. 2018 Jun 15;7(6):1618-1628. doi: 10.1021/acssynbio.8b00100. Epub  2018 Jun 5. [PubMed:29763307  ] 
  14. Sattasathuchana P, Allenspach K, Lopes R, Suchodolski JS, Steiner JM: Evaluation of Serum 3-Bromotyrosine Concentrations in Dogs with Steroid-Responsive Diarrhea and Food-Responsive Diarrhea. J Vet Intern Med. 2017 Jul;31(4):1056-1061. doi: 10.1111/jvim.14742. Epub 2017  Jun 19. [PubMed:28626891  ] 
  15. Sattasathuchana P, Berghoff N, Grutzner N, Thengchaisri N, Rangachari VR, Suchodolski JS, Steiner JM: Development and analytic validation of an electron ionization gas chromatography/mass spectrometry (EI-GC/MS) method for the measurement of 3-bromotyrosine in canine serum. Vet Clin Pathol. 2016 Sep;45(3):515-23. doi: 10.1111/vcp.12373. Epub 2016 Jul 18. [PubMed:27428603  ] 
  16. Cunnion KM, Willis LK, Minto HB, Burch TC, Werner AL, Shah TA, Krishna NK, Nyalwidhe JO, Maples KM: Eosinophil Quantitated Urine Kinetic: A novel assay for assessment of eosinophilic esophagitis. Ann Allergy Asthma Immunol. 2016 May;116(5):435-9. doi:  10.1016/j.anai.2016.02.011. Epub 2016 Mar 24. [PubMed:27017558  ] 
  17. Sattasathuchana P, Grutzner N, Lopes R, Guard BC, Suchodolski JS, Steiner JM: Stability of 3-bromotyrosine in serum and serum 3-bromotyrosine concentrations in dogs with gastrointestinal diseases. BMC Vet Res. 2015 Jan 17;11:5. doi: 10.1186/s12917-015-0321-0. [PubMed:25595676  ] 
  18. Kolisetty N, Bull RJ, Muralidhara S, Costyn LJ, Delker DA, Guo Z, Cotruvo JA, Fisher JW, Cummings BS: Association of brominated proteins and changes in protein expression in the rat kidney with subcarcinogenic to carcinogenic doses of bromate. Toxicol Appl Pharmacol. 2013 Oct 15;272(2):391-8. doi:  10.1016/j.taap.2013.06.018. Epub 2013 Jun 26. [PubMed:23811332  ] 
  19. Thomson E, Brennan S, Senthilmohan R, Gangell CL, Chapman AL, Sly PD, Kettle AJ, Balding E, Berry LJ, Carlin JB, Carzino R, de Klerk N, Douglas T, Foo C, Garratt LW, Hall GL, Harrison J, Kicic A, Laing IA, Logie KM, Massie J, Mott LS, Murray C, Parsons F, Pillarisetti N, Poreddy SR, Ranganathan SC, Robertson CF, Robins-Browne R, Robinson PJ, Skoric B, Stick SM, Sutanto EN, Williamson E: Identifying peroxidases and their oxidants in the early pathology of cystic fibrosis. Free Radic Biol Med. 2010 Nov 15;49(9):1354-60. doi:  10.1016/j.freeradbiomed.2010.07.010. Epub 2010 Jul 18. [PubMed:20647044  ]