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Showing NP-Card for Rose bengal (NP0338323)

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Record Information
Version2.0
Created at2024-09-11 14:54:38 UTC
Updated at2024-09-11 14:54:38 UTC
NP-MRD IDNP0338323
Secondary Accession NumbersNone
Natural Product Identification
Common NameRose bengal
DescriptionRose bengal, also known as ak-rose liq 1% or c.I. 45440, Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. Its sodium salt is commonly used in eye drops to stain damaged conjunctival and corneal cells and thereby identify damage to the eye. Rose bengal is a drug. Rose bengal is a moderately basic compound (based on its pKa). Rose bengal is a food colourant; no longer FDA permitted Rose Bengal (4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein) is a stain. Rose bengal was first documented in 1987 (PMID: 2821977). Rose Bengal (4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein) is a stain.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0338323 (Rose bengal)


  Mrv0541 01101307162D          

 33 36  0  0  0  0            999 V2000
   -5.4214   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -6.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -7.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -6.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -2.2393    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504   -4.7143    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -2.2393    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -4.7143    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -5.5393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -7.1893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -8.0143    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -7.1893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -5.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0048   -4.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  1 21  1  0  0  0  0
  2 22  2  0  0  0  0
  3 23  1  0  0  0  0
 11 24  1  0  0  0  0
 14 25  1  0  0  0  0
 13 26  1  0  0  0  0
 20 27  1  0  0  0  0
 19 28  1  0  0  0  0
 18 29  1  0  0  0  0
 17 30  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
Download

3D MOL for NP0338323 (Rose bengal)

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3D SDF for NP0338323 (Rose bengal)

  Mrv0541 01101307162D          

 33 36  0  0  0  0            999 V2000
   -5.4214   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070   -6.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -7.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -6.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -2.2393    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504   -4.7143    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -2.2393    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -4.7143    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -5.5393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -7.1893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -8.0143    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -7.1893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1359   -5.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0048   -4.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  1 21  1  0  0  0  0
  2 22  2  0  0  0  0
  3 23  1  0  0  0  0
 11 24  1  0  0  0  0
 14 25  1  0  0  0  0
 13 26  1  0  0  0  0
 20 27  1  0  0  0  0
 19 28  1  0  0  0  0
 18 29  1  0  0  0  0
 17 30  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)

> <INCHI_KEY>
VDNLFJGJEQUWRB-UHFFFAOYSA-N

> <FORMULA>
C20H4Cl4I4O5

> <MOLECULAR_WEIGHT>
973.673

> <EXACT_MASS>
971.499157746

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
63.79911175730519

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid

> <ALOGPS_LOGP>
6.02

> <JCHEM_LOGP>
9.258434683

> <ALOGPS_LOGS>
-6.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.377386046053799

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5245253021335605

> <JCHEM_PKA_STRONGEST_BASIC>
1.8122483464241397

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
176.0548

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.81e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rose bengal

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0338323 (Rose bengal)
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PDB for NP0338323 (Rose bengal)
HEADER    PROTEIN                                 10-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JAN-13         0                                  
HETATM    1  C   UNK     0     -10.120  -5.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.454  -6.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.454  -8.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.120  -8.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.786  -8.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.786  -6.490   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.453  -5.720   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.453  -8.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.119  -8.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.119  -6.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.785  -5.720   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.785  -8.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.452  -8.030   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.452  -6.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.453 -10.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.786 -11.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.786 -12.650   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.453 -13.420   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.119 -12.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.119 -11.110   0.000  0.00  0.00           C+0
HETATM   21  I   UNK     0     -10.120  -4.180   0.000  0.00  0.00           I+0
HETATM   22  O   UNK     0     -12.787  -5.720   0.000  0.00  0.00           O+0
HETATM   23  I   UNK     0     -12.787  -8.800   0.000  0.00  0.00           I+0
HETATM   24  I   UNK     0      -4.785  -4.180   0.000  0.00  0.00           I+0
HETATM   25  O   UNK     0      -2.118  -5.720   0.000  0.00  0.00           O+0
HETATM   26  I   UNK     0      -2.118  -8.800   0.000  0.00  0.00           I+0
HETATM   27 Cl   UNK     0      -4.785 -10.340   0.000  0.00  0.00          Cl+0
HETATM   28 Cl   UNK     0      -4.785 -13.420   0.000  0.00  0.00          Cl+0
HETATM   29 Cl   UNK     0      -7.453 -14.960   0.000  0.00  0.00          Cl+0
HETATM   30 Cl   UNK     0     -10.120 -13.420   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0     -10.120 -10.340   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -11.454 -11.110   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -11.209  -9.251   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    7   11    9                                                  
CONECT   11   10   14   24                                                  
CONECT   12    9   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   11   25                                                  
CONECT   15    8   16   20                                                  
CONECT   16   15   17   31                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   20   28                                                  
CONECT   20   15   19   27                                                  
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24   11                                                            
CONECT   25   14                                                            
CONECT   26   13                                                            
CONECT   27   20                                                            
CONECT   28   19                                                            
CONECT   29   18                                                            
CONECT   30   17                                                            
CONECT   31   16   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

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3D PDB for NP0338323 (Rose bengal)
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SMILES for NP0338323 (Rose bengal)
OC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12
Download
INCHI for NP0338323 (Rose bengal)
InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)
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View in JSmol
Synonyms
ValueSource
2',4',5',7'-Tetrabromo-2,3,4,5-tetraiodofluoresceinChEBI
3,4,5,6-Tetrachloro-2',4',5',7'-tetraiodofluorescein, 8ciHMDB
4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 9ciHMDB
Ak-rose liq 1%HMDB
C.I. 45440HMDB
C.I. solvent red 141HMDB
Bengal, roseMeSH
Rose bengalMeSH
Rose bengal sodium I 125MeSH
Rose bengal sodium I 131MeSH
Chemical FormulaC20H4Cl4I4O5
Average Mass973.6730 Da
Monoisotopic Mass971.49916 Da
IUPAC Name2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid
Traditional Namerose bengal
CAS Registry NumberNot Available
SMILES
OC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12
InChI Identifier
InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)
InChI KeyVDNLFJGJEQUWRB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct ParentXanthenes  
Alternative Parents
Substituents
  • Xanthene
    • 

  • 2-halobenzoic acid or derivatives
    • 

  • 3-halobenzoic acid or derivatives
    • 

  • 4-halobenzoic acid or derivatives
    • 

  • Halobenzoic acid or derivatives
    • 

  • 2-halobenzoic acid
    • 

  • 3-halobenzoic acid
    • 

  • 4-halobenzoic acid
    • 

  • Halobenzoic acid
    • 

  • Benzoic acid
    • 

  • Benzoic acid or derivatives
    • 

  • Benzoyl
    • 

  • 2-iodophenol
    • 

  • 1-carboxy-2-haloaromatic compound
    • 

  • Chlorobenzene
    • 

  • Halobenzene
    • 

  • Monocyclic benzene moiety
    • 

  • Aryl iodide
    • 

  • Aryl halide
    • 

  • Benzenoid
    • 

  • Aryl chloride
    • 

  • Vinylogous halide
    • 

  • Heteroaromatic compound
    • 

  • Cyclic ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organohalogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organochloride
    • 

  • Organoiodide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP6.02ALOGPS
logP9.26ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)1.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity176.05 m³·mol⁻¹ChemAxon
Polarizability63.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036613  
DrugBank IDDB11182  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015529  
KNApSAcK IDNot Available
Chemspider ID23774  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRose bengal  
METLIN IDNot Available
PubChem Compound25474  
PDB IDNot Available
ChEBI ID87202  
Good Scents IDNot Available
References
General References
  1. Roat MI, Romanowski E, Araullo-Cruz T, Gordon YJ: The antiviral effects of rose bengal and fluorescein. Arch Ophthalmol. 1987 Oct;105(10):1415-7. doi:  10.1001/archopht.1987.01060100117039. [PubMed:2821977  ]