NP-MRD: Showing NP-Card for Dityrosine (NP0087449)

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Record Information

Version

2.0

Created at

2022-05-11 16:49:58 UTC

Updated at

2022-05-11 16:49:58 UTC

NP-MRD ID

NP0087449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dityrosine

Description

Dityrosine, also known as O,o'-dityrosine, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Dityrosine has also been found in oxidative/nitrative stress under a variety of conditions and biological systems. Dityrosine is a very strong basic compound (based on its pKa). Dityrosine is a fluorescent molecule formed as a result of normal posttranslational processing. The continued development of, and increased accessibility to, improved mass spectrometric instrumentation will expand the capability, feasibility, and sensitivity with which specific biomarkers like dityrosine can be measured. The presence of elevated levels of dityrosine in mammalian tissue and urine samples has been measured by chromatographic separation followed by mass spectrometry GC-MS and HPLC-MS/MS. Increases in dityrosine levels have been associated with pathologies such as eye cataracts, atherosclerosis, acute inflammation, and Alzheimer's disease. Dityrosine was first documented in 1997 (PMID: 9323538). In this regard, it has been used as an important biomarker for oxidatively modified proteins during UV and gamma-irradiation, aging, and exposure to oxygen free radicals, nitrogen dioxide, peroxynitrite, and lipid hydroperoxides (PMID: 10211406) (PMID: 17019703).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220322D          

 26 27  0  0  0  0            999 V2000
   14.6370   -9.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -9.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -10.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -11.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -10.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225   -9.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -11.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -12.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -13.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -12.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -14.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -14.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -15.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -14.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370   -8.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -8.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -7.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659   -8.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659  -11.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -11.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659   -6.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370   -6.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -15.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -15.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  1  2  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 12  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 22 12  1  0  0  0  0
 23 19  1  0  0  0  0
 24 19  2  0  0  0  0
 25 15  1  0  0  0  0
 26 15  2  0  0  0  0
M  END

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
    5.8082    0.6010    0.7472 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -0.6365    0.0354 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8595   -1.6520    0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4591   -1.2040    0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372   -0.5281    1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6288   -0.1118    1.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -0.3689    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032    0.1325    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9702    0.8979   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    1.3833   -0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1254    1.1044    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5194    1.6032    0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997    0.6459   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5232   -0.6359    0.3810 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8402    1.2681   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0775    2.4214   -0.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8514    0.5613    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    0.3319    1.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.1592    1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8499   -0.9433    2.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3681   -1.0420   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388   -1.3201   -1.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.4573   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6617   -0.3778   -1.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -1.3204   -2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4812    0.9086   -1.8623 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2080    0.5500    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.4108    0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -1.0860    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.0100    1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519   -2.5440   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5201   -0.3201    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975    0.4266    2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    1.1731   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    1.9926   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7592    1.8625    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    2.5326   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2135    0.5445   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6574   -0.6230    1.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7593   -1.2751    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3293   -0.1483   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2544    0.0888    2.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -1.1448    3.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -1.0920   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -1.9870   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2898    1.5464   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 18  2  0
 18 19  1  0
 19 20  1  0
 19  8  2  0
  8  9  1  0
  9 10  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 24  1  0
 24 26  1  0
 24 25  2  0
  4 23  1  0
 23 21  2  0
 21 22  1  0
 13 15  1  0
 15 17  1  0
 15 16  2  0
 10 11  1  0
 21  7  1  0
 14 39  1  0
 14 40  1  0
 13 38  1  6
 12 36  1  0
 12 37  1  0
 18 42  1  0
 20 43  1  0
  9 34  1  0
 10 35  1  0
  6 33  1  0
  5 32  1  0
  3 30  1  0
  3 31  1  0
  2 29  1  6
  1 27  1  0
  1 28  1  0
 26 46  1  0
 23 45  1  0
 22 44  1  0
 17 41  1  0
M  END


  Mrv0541 02231220322D          

 26 27  0  0  0  0            999 V2000
   14.6370   -9.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -9.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -10.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -11.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -10.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225   -9.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -11.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -12.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -13.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -12.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -14.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -14.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225  -15.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -14.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370   -8.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -8.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3515   -7.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659   -8.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659  -11.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -11.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659   -6.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370   -6.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081  -15.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6370  -15.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  1  2  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 12  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 22 12  1  0  0  0  0
 23 19  1  0  0  0  0
 24 19  2  0  0  0  0
 25 15  1  0  0  0  0
 26 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2O6/c19-13(17(23)24)5-9-1-3-11(15(21)7-9)12-4-2-10(8-16(12)22)6-14(20)18(25)26/h1-4,7-8,13-14,21-22H,5-6,19-20H2,(H,23,24)(H,25,26)

> <INCHI_KEY>
FHOZGLMQYMAREG-UHFFFAOYSA-N

> <FORMULA>
C18H20N2O6

> <MOLECULAR_WEIGHT>
360.3612

> <EXACT_MASS>
360.132136382

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
37.148717607940924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-3.303332861231999

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.160947424898312

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5581509824068345

> <JCHEM_PKA_STRONGEST_BASIC>
9.942039122285927

> <JCHEM_POLAR_SURFACE_AREA>
167.1

> <JCHEM_REFRACTIVITY>
93.27259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.322 -17.492   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.656 -18.262   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.656 -19.802   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.322 -20.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.989 -19.802   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.989 -18.262   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.322 -22.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.656 -22.882   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.656 -24.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.322 -25.192   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.989 -24.422   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.989 -22.882   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.322 -26.732   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.989 -27.502   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.989 -29.042   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      24.655 -26.732   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      27.322 -15.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.656 -15.182   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.656 -13.642   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      29.990 -15.952   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      29.990 -20.572   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      24.655 -22.112   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      29.990 -12.872   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      27.322 -12.872   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      24.655 -29.812   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      27.322 -29.812   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   22                                                  
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   25   26                                                  
CONECT   16   14                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   23   24                                                  
CONECT   20   18                                                            
CONECT   21    3                                                            
CONECT   22   12                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
CONECT   25   15                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
Bityrosine	HMDB
O,O'-dityrosine	HMDB
O,O-Dityrosine	HMDB
2-Amino-3-[4'-(2-amino-2-carboxyethyl)-2,2'-dihydroxy-[1,1'-biphenyl]-4-yl]propanoate	HMDB

Chemical Formula

C₁₈H₂₀N₂O₆

Average Mass

360.3612 Da

Monoisotopic Mass

360.13214 Da

IUPAC Name

2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid

Traditional Name

2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid

CAS Registry Number

Not Available

SMILES

NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=O

InChI Identifier

InChI=1S/C18H20N2O6/c19-13(17(23)24)5-9-1-3-11(15(21)7-9)12-4-2-10(8-16(12)22)6-14(20)18(25)26/h1-4,7-8,13-14,21-22H,5-6,19-20H2,(H,23,24)(H,25,26)

InChI Key

FHOZGLMQYMAREG-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Phenylalanine or derivatives
Neolignan skeleton
Biphenyl
3-phenylpropanoic-acid
Alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid
Carboxylic acid derivative
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
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	-2.8	ALOGPS
logP	-3.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	167.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.27 m³·mol⁻¹	ChemAxon
Polarizability	37.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006045

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023818

KNApSAcK ID

Not Available

Chemspider ID

21233943

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477799

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abdelrahim M, Morris E, Carver J, Facchina S, White A, Verma A: Liquid chromatographic assay of dityrosine in human cerebrospinal fluid. J Chromatogr B Biomed Sci Appl. 1997 Aug 29;696(2):175-82. doi: 10.1016/s0378-4347(97)00248-x. [PubMed:9323538 ]
Galeazzi L, Ronchi P, Franceschi C, Giunta S: In vitro peroxidase oxidation induces stable dimers of beta-amyloid (1-42) through dityrosine bridge formation. Amyloid. 1999 Mar;6(1):7-13. doi: 10.3109/13506129908993282. [PubMed:10211406 ]
DiMarco T, Giulivi C: Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples. Mass Spectrom Rev. 2007 Jan-Feb;26(1):108-20. doi: 10.1002/mas.20109. [PubMed:17019703 ]

Showing NP-Card for Dityrosine (NP0087449)

MOL for NP0087449 (Dityrosine)

3D MOL for NP0087449 (Dityrosine)

3D SDF for NP0087449 (Dityrosine)

3D-SDF for NP0087449 (Dityrosine)

PDB for NP0087449 (Dityrosine)

3D PDB for NP0087449 (Dityrosine)

SMILES for NP0087449 (Dityrosine)

INCHI for NP0087449 (Dityrosine)

Structure for NP0087449 (Dityrosine)

3D Structure for NP0087449 (Dityrosine)