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Showing metabocard for 4-Nitrophenyl acetate (HMDB0246538)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:33:18 UTC
Update Date2021-10-01 18:51:06 UTC
HMDB IDHMDB0246538
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Nitrophenyl acetate
Description4-Nitrophenyl acetate, also known as p-nitrophenol acetic acid or 4-O2nc6H4oac, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Based on a literature review a significant number of articles have been published on 4-Nitrophenyl acetate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-nitrophenyl acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Nitrophenyl acetate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0246538 (4-Nitrophenyl acetate)

  Mrv1652309112101332D          

 13 13  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  CHG  2  11   1  13  -1
M  END
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3D MOL for HMDB0246538 (4-Nitrophenyl acetate)

HMDB0246538
     RDKit          3D
4-Nitrophenyl acetate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.9653   -0.3292    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4894   -0.3224    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -0.9273    1.4821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647    0.3153   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    0.2706   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816    1.2233    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    1.1780    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    0.1627   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232    0.0607   -0.3910 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.3676   -0.8646   -0.9857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5757    0.9942    0.2501 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6731   -0.7824   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073   -0.7351   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4437   -0.5498   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3839    0.6042    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850   -1.1476    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    2.0245    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    1.9150    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074   -1.5982   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.4917   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   9   1  11  -1
M  END
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3D SDF for HMDB0246538 (4-Nitrophenyl acetate)

  Mrv1652309112101332D          

 13 13  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  CHG  2  11   1  13  -1
M  END
> <DATABASE_ID>
HMDB0246538

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO4/c1-6(10)13-8-4-2-7(3-5-8)9(11)12/h2-5H,1H3

> <INCHI_KEY>
QAUUDNIGJSLPSX-UHFFFAOYSA-N

> <FORMULA>
C8H7NO4

> <MOLECULAR_WEIGHT>
181.147

> <EXACT_MASS>
181.037507709

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.61446880134693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-nitrophenyl acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.5204909796666661

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.138606039252213

> <JCHEM_POLAR_SURFACE_AREA>
69.44

> <JCHEM_REFRACTIVITY>
43.51090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-nitrophenylacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0246538 (4-Nitrophenyl acetate)

HMDB0246538
     RDKit          3D
4-Nitrophenyl acetate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.9653   -0.3292    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4894   -0.3224    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -0.9273    1.4821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647    0.3153   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    0.2706   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816    1.2233    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    1.1780    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    0.1627   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232    0.0607   -0.3910 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.3676   -0.8646   -0.9857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5757    0.9942    0.2501 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6731   -0.7824   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073   -0.7351   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4437   -0.5498   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3839    0.6042    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850   -1.1476    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    2.0245    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    1.9150    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074   -1.5982   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.4917   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   9   1  11  -1
M  END
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PDB for HMDB0246538 (4-Nitrophenyl acetate)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0246538 (4-Nitrophenyl acetate)

COMPND    HMDB0246538
HETATM    1  C1  UNL     1       3.965  -0.329   0.657  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.489  -0.322   0.592  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.812  -0.927   1.482  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.765   0.315  -0.400  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.354   0.271  -0.385  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.382   1.223   0.268  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.749   1.178   0.282  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.420   0.163  -0.368  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.823   0.061  -0.391  1.00  0.00           N1+
HETATM   10  O3  UNL     1      -4.368  -0.865  -0.986  1.00  0.00           O  
HETATM   11  O4  UNL     1      -4.576   0.994   0.250  1.00  0.00           O1-
HETATM   12  C7  UNL     1      -1.673  -0.782  -1.017  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.307  -0.735  -1.029  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.444  -0.550  -0.320  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.384   0.604   1.088  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.285  -1.148   1.351  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.130   2.024   0.782  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.369   1.915   0.789  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.207  -1.598  -1.539  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.246  -1.492  -1.546  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   12
CONECT    9   10   10   11
CONECT   12   13   13   19
CONECT   13   20
END
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SMILES for HMDB0246538 (4-Nitrophenyl acetate)

CC(=O)OC1=CC=C(C=C1)[N+]([O-])=O
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INCHI for HMDB0246538 (4-Nitrophenyl acetate)

InChI=1S/C8H7NO4/c1-6(10)13-8-4-2-7(3-5-8)9(11)12/h2-5H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-O2nc6H4OAcChEBI
Acetic acid p-nitrophenyl esterChEBI
p-AcetoxynitrobenzeneChEBI
p-Nitrophenol acetateChEBI
p-Nitrophenyl acetateChEBI
Acetate p-nitrophenyl esterGenerator
p-Nitrophenol acetic acidGenerator
p-Nitrophenyl acetic acidGenerator
4-Nitrophenyl acetic acidGenerator
4-Nitrophenyl acetate, 14C-labeledHMDB
Para-nitrophenyl acetateHMDB
Chemical FormulaC8H7NO4
Average Molecular Weight181.147
Monoisotopic Molecular Weight181.037507709
IUPAC Name4-nitrophenyl acetate
Traditional NameP-nitrophenylacetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C8H7NO4/c1-6(10)13-8-4-2-7(3-5-8)9(11)12/h2-5H,1H3
InChI KeyQAUUDNIGJSLPSX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Nitrobenzene
  • Phenoxy compound
  • Nitroaromatic compound
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • C-nitro compound
  • Organic nitro compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-f12a7f9ed72c8e4536a32021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12687
KEGG Compound IDNot Available
BioCyc IDP-NITROPHENYL-ACETATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13243
PDB IDNot Available
ChEBI ID82635
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details
1. Dioscorin DB3S
General function:
Not Available
Specific function:
Storage protein of tuber. Involved in protection against oxidative stress (Probable). Has carbonate dehydratase and weak trypsin inhibitor activity detected by measuring the dehydration of sodium bicarbonate and the inhibition of trypsin-catalyzed hydrolysis of N-benzoyl-L-arginine-4-nitro anilide, respectively (PubMed:10552514). Contrarily, no carbonate dehydratase or trypsin inhibitor activity detected by measuring the hydrolysis of 4-nitrophenyl acetate or the inhibition of bovine trypsin-catalyzed hydrolysis of N-benzoyl-L-arginine ethyl ester, respectively (PubMed:15047697). Has dehydroascorbate (DHA) reductase and monodehydroascorbate (MDA) reductase activities (Ref.5). Catalyzes the reactions of carbonate dehydratase and DHA reductase independently of zinc and glutathione (GSH). The coupled reaction is capable of recycling a plant antioxidant ascorbate using ubiquitous compounds H(2)O and CO(2) (By similarity). Exhibits antioxidant activity. Able to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and hydroxyl radicals (PubMed:11600050). Exhibits immunomodulatory activity. Activates Toll-like receptor 4 signaling pathways by up-regulating the gene expression of proinflammatory cytokines, such as tumor necrosis factor alpha, interleukin-1 beta and interleukin-6, and chemokines RANTES and MCP-1, in mouse RAW 264.7 macrophages. Stimulates the phagocytosis of E.coli by the LPS-treated mouse macrophages (By similarity).
Gene Name:
DB3S
Uniprot ID:
Q75N34
Molecular weight:
30460.195