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Showing NP-Card for Norepinephrine (NP0000446)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:21 UTC
NP-MRD IDNP0000446
Secondary Accession NumbersNone
Natural Product Identification
Common NameNorepinephrine
DescriptionPrecursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000446 (Norepinephrine)


  Mrv1652309172005022D          

 12 12  0  0  0  0            999 V2000
 9999.5287 9999.1909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.2428 9998.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.528710000.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.9590 9999.1909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6668 9999.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6668 9997.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8115 9998.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0972 9999.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3827 9998.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3827 9997.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0971 9997.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8116 9997.9531    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  1  0  0  0
  2  4  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000446 (Norepinephrine)

HMDB0000216
     RDKit          3D
Norepinephrine
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.3518    0.9219    0.7915 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752   -0.2325   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661   -0.3378   -1.0674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5757   -1.4805   -1.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -0.2922   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -1.4086    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.3710    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5103   -0.2154    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -0.2159    1.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001    0.8947    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528    2.0534    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.8518   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368    0.6600    1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    1.5842    0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -1.1309    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4451   -0.1773   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    0.5273   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -1.3461   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -2.3061    0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463   -2.2496    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3093    0.6624    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4070    2.8799   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3603    1.7284   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  6
  4 18  1  0
  6 19  1  0
  7 20  1  0
  9 21  1  0
 11 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0000446 (Norepinephrine)


  Mrv1652309172005022D          

 12 12  0  0  0  0            999 V2000
 9999.5287 9999.1909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.2428 9998.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.528710000.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.9590 9999.1909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6668 9999.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6668 9997.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8115 9998.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0972 9999.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3827 9998.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3827 9997.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0971 9997.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8116 9997.9531    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  1  0  0  0
  2  4  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC[C@H](O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1

> <INCHI_KEY>
SFLSHLFXELFNJZ-QMMMGPOBSA-N

> <FORMULA>
C8H11NO3

> <MOLECULAR_WEIGHT>
169.1778

> <EXACT_MASS>
169.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.95880867290888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

> <JCHEM_LOGP>
-0.6835133951859954

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.652756385089422

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.500884650011601

> <JCHEM_PKA_STRONGEST_BASIC>
8.84847263942599

> <JCHEM_POLAR_SURFACE_AREA>
86.71

> <JCHEM_REFRACTIVITY>
44.4557

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
norepinephrine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000446 (Norepinephrine)

HMDB0000216
     RDKit          3D
Norepinephrine
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.3518    0.9219    0.7915 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752   -0.2325   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661   -0.3378   -1.0674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5757   -1.4805   -1.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -0.2922   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -1.4086    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.3710    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5103   -0.2154    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -0.2159    1.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001    0.8947    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528    2.0534    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.8518   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368    0.6600    1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    1.5842    0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -1.1309    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4451   -0.1773   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    0.5273   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -1.3461   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -2.3061    0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463   -2.2496    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3093    0.6624    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4070    2.8799   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3603    1.7284   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  6
  4 18  1  0
  6 19  1  0
  7 20  1  0
  9 21  1  0
 11 22  1  0
 12 23  1  0
M  END
Download

PDB for NP0000446 (Norepinephrine)

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.7878665.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.1208664.386   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.7878666.698   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0    8668.4578665.156   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    8660.4458665.156   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.4458662.073   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8664.4488664.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.1158665.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.7818664.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.7818662.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.1158662.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.4488662.846   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    9                                                            
CONECT    6   10                                                            
CONECT    7    8   12    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0000446 (Norepinephrine)

COMPND    HMDB0000216
HETATM    1  N1  UNL     1      -2.352   0.922   0.791  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.475  -0.232  -0.050  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.366  -0.338  -1.067  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.576  -1.480  -1.827  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.026  -0.292  -0.443  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.486  -1.409   0.178  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.753  -1.371   0.771  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.510  -0.215   0.741  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.779  -0.216   1.346  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.000   0.895   0.122  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.753   2.053   0.090  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.739   0.852  -0.465  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.337   0.660   1.802  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.154   1.584   0.683  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.534  -1.131   0.597  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.445  -0.177  -0.585  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.487   0.527  -1.774  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.376  -1.346  -2.366  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.115  -2.306   0.195  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.146  -2.250   1.255  1.00  0.00           H  
HETATM   21  H9  UNL     1       4.309   0.662   1.303  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.407   2.880  -0.355  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.360   1.728  -0.942  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3   15   16
CONECT    3    4    5   17
CONECT    4   18
CONECT    5    6    6   12
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   10
CONECT    9   21
CONECT   10   11   12   12
CONECT   11   22
CONECT   12   23
END
Download

SMILES for NP0000446 (Norepinephrine)

NC[C@H](O)C1=CC(O)=C(O)C=C1
Download

INCHI for NP0000446 (Norepinephrine)

InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-ArterenolChEBI
(-)-NoradrenalineChEBI
(-)-NorepinephrineChEBI
(R)-(-)-NorepinephrineChEBI
(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolChEBI
(R)-NorepinephrineChEBI
4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediolChEBI
ArterenolChEBI
L-NoradrenalineChEBI
L-NOREPINEPHRINEChEBI
NoradrenalineChEBI
NorepinefrinaChEBI
NorepinephrinumChEBI
(-)-(R)-NorepinephrineHMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcoholHMDB
(R)-NoradrenalineHMDB
4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolHMDB
AdrenorHMDB
AktaminHMDB
L-2-Amino-1-(3,4-dihydroxyphenyl)ethanolHMDB
L-3,4-DihydroxyphenylethanolamineHMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcoholHMDB
L-ArterenolHMDB
LevarterenolHMDB
LevoarterenolHMDB
LevonorHMDB
LevonoradrenalineHMDB
LevonorepinephrineHMDB
LevophedHMDB
Nor-epirenanHMDB
NoradrenalinHMDB
NorartrinalHMDB
NorepirenamineHMDB
Sympathin eHMDB
Chemical FormulaC8H11NO3
Average Mass169.1778 Da
Monoisotopic Mass169.07389 Da
IUPAC Name4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Traditional Namenorepinephrine
CAS Registry Number51-41-2
SMILES
NC[C@H](O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChI KeySFLSHLFXELFNJZ-QMMMGPOBSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-01View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-01View Spectrum
Species
Species of Origin
Species NameSourceReference
Albizia julibrissinPlant
Apis ceranaLOTUS Database
Brassica olereaceaPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Crataegus rhipidophyllaLOTUS Database
Cytisus copariusPlant
Hololena curtaLOTUS Database
Mimosa pudicaPlant
Mus musculusLOTUS Database
Musa acuminataPlant
Musa paradisiacaLOTUS Database
Musa x paradisiacaPlant
Passiflora quadrangularisPlant
Persea americanaPlant
Phaseolus coccineusPlant
Phaseolus vulgarisPlant
Pisum sativumPlant
Plantago majorPlant
Portulaca grandifloraPlant
Portulaca oleraceaPlant
Samanea samanPlant
Solanum lycopersicumPlant
Solanum melanogenaPlant
Solanum tuberosumPlant
Spinacia oleraceaPlant
Theobroma cacaoPlant
Triticum aestivumPlant
Vicia fabaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145.2 - 146.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility849 mg/mLNot Available
LogP-1.24Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility12.5 g/LALOGPS
logP-0.68ChemAxon
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.46 m³·mol⁻¹ChemAxon
Polarizability16.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000216
DrugBank IDDB00368
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097322
KNApSAcK IDC00001424
Chemspider ID388394
KEGG Compound IDC00547
BioCyc IDNot Available
BiGG ID35313
Wikipedia LinkNorepinephrine
METLIN ID5226
PubChem Compound439260
PDB IDNot Available
ChEBI ID18357
Good Scents IDrw1341221
References
General References
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