Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:46:25 UTC

Update Date

2022-03-07 02:54:59 UTC

HMDB ID

HMDB0036613

Secondary Accession Numbers

HMDB36613

Metabolite Identification

Common Name

Rose bengal

Description

Rose bengal 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. Based on a literature review very few articles have been published on Rose bengal.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  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

HMDB0036613
     RDKit          3D
Rose bengal
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.0078   -1.4552   -2.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146   -0.2541   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.7154   -2.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    0.0388   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585    0.2482    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    0.1552   -1.2407 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.5269    1.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6509    0.7956    1.7605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.5860    2.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.9409    3.9526 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    0.3759    1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.4625    3.1766 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.0944    0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.1280    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -1.4040    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -2.4894    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -3.7520    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -5.3564    1.3209 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351   -3.9104    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -5.0766    0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -2.8930    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5874   -3.1864   -0.5101 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.6112   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558   -0.5891   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598    0.6263   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0420    1.6967   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0760    1.3887   -1.3468 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    2.9943   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    4.0495   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    3.2393   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5556    5.2183   -0.6809 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    2.1848   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236    0.8906   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9045   -3.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1800   -2.3206    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878    3.8829   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    2.4107    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 13  4  1  0
 33 14  1  0
 23 15  1  0
 33 25  1  0
  3 34  1  0
 16 35  1  0
 29 36  1  0
 32 37  1  0
M  END


  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>
HMDB0036613

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0036613
     RDKit          3D
Rose bengal
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.0078   -1.4552   -2.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146   -0.2541   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.7154   -2.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    0.0388   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585    0.2482    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    0.1552   -1.2407 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.5269    1.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6509    0.7956    1.7605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.5860    2.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.9409    3.9526 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    0.3759    1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.4625    3.1766 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.0944    0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.1280    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -1.4040    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -2.4894    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -3.7520    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -5.3564    1.3209 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351   -3.9104    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -5.0766    0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -2.8930    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5874   -3.1864   -0.5101 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.6112   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558   -0.5891   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598    0.6263   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0420    1.6967   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0760    1.3887   -1.3468 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    2.9943   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    4.0495   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    3.2393   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5556    5.2183   -0.6809 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    2.1848   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236    0.8906   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9045   -3.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1800   -2.3206    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878    3.8829   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    2.4107    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 13  4  1  0
 33 14  1  0
 23 15  1  0
 33 25  1  0
  3 34  1  0
 16 35  1  0
 29 36  1  0
 32 37  1  0
M  END

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

COMPND    HMDB0036613
HETATM    1  O1  UNL     1       2.008  -1.455  -2.065  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.015  -0.254  -1.696  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.721   0.715  -2.637  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.331   0.039  -0.304  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.658   0.248   0.017  1.00  0.00           C  
HETATM    6 CL1  UNL     1       4.889   0.155  -1.241  1.00  0.00          CL  
HETATM    7  C4  UNL     1       3.976   0.527   1.331  1.00  0.00           C  
HETATM    8 CL2  UNL     1       5.651   0.796   1.760  1.00  0.00          CL  
HETATM    9  C5  UNL     1       2.966   0.586   2.270  1.00  0.00           C  
HETATM   10 CL3  UNL     1       3.356   0.941   3.953  1.00  0.00          CL  
HETATM   11  C6  UNL     1       1.644   0.376   1.942  1.00  0.00           C  
HETATM   12 CL4  UNL     1       0.394   0.462   3.177  1.00  0.00          CL  
HETATM   13  C7  UNL     1       1.311   0.094   0.622  1.00  0.00           C  
HETATM   14  C8  UNL     1      -0.081  -0.128   0.270  1.00  0.00           C  
HETATM   15  C9  UNL     1      -0.599  -1.404   0.322  1.00  0.00           C  
HETATM   16  C10 UNL     1       0.148  -2.489   0.696  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.415  -3.752   0.733  1.00  0.00           C  
HETATM   18  I1  UNL     1       0.818  -5.356   1.321  1.00  0.00           I  
HETATM   19  C12 UNL     1      -1.735  -3.910   0.392  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.236  -5.077   0.432  1.00  0.00           O  
HETATM   21  C13 UNL     1      -2.559  -2.893   0.007  1.00  0.00           C  
HETATM   22  I2  UNL     1      -4.587  -3.186  -0.510  1.00  0.00           I  
HETATM   23  C14 UNL     1      -2.019  -1.611  -0.040  1.00  0.00           C  
HETATM   24  O4  UNL     1      -2.756  -0.589  -0.401  1.00  0.00           O  
HETATM   25  C15 UNL     1      -2.260   0.626  -0.449  1.00  0.00           C  
HETATM   26  C16 UNL     1      -3.042   1.697  -0.830  1.00  0.00           C  
HETATM   27  I3  UNL     1      -5.076   1.389  -1.347  1.00  0.00           I  
HETATM   28  C17 UNL     1      -2.582   2.994  -0.902  1.00  0.00           C  
HETATM   29  O5  UNL     1      -3.427   4.050  -1.298  1.00  0.00           O  
HETATM   30  C18 UNL     1      -1.265   3.239  -0.574  1.00  0.00           C  
HETATM   31  I4  UNL     1      -0.556   5.218  -0.681  1.00  0.00           I  
HETATM   32  C19 UNL     1      -0.452   2.185  -0.187  1.00  0.00           C  
HETATM   33  C20 UNL     1      -0.924   0.891  -0.119  1.00  0.00           C  
HETATM   34  H1  UNL     1       2.312   0.904  -3.444  1.00  0.00           H  
HETATM   35  H2  UNL     1       1.180  -2.321   0.956  1.00  0.00           H  
HETATM   36  H3  UNL     1      -4.388   3.883  -1.538  1.00  0.00           H  
HETATM   37  H4  UNL     1       0.580   2.411   0.064  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   34
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    7    8    9    9
CONECT    9   10   11
CONECT   11   12   13   13
CONECT   13   14
CONECT   14   15   15   33
CONECT   15   16   23
CONECT   16   17   17   35
CONECT   17   18   19
CONECT   19   20   20   21
CONECT   21   22   23   23
CONECT   23   24
CONECT   24   25
CONECT   25   26   26   33
CONECT   26   27   28
CONECT   28   29   30   30
CONECT   29   36
CONECT   30   31   32
CONECT   32   33   33   37
END

HMDB0036613
     RDKit          3D
Rose bengal
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.0078   -1.4552   -2.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146   -0.2541   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.7154   -2.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    0.0388   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585    0.2482    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    0.1552   -1.2407 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.5269    1.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6509    0.7956    1.7605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.5860    2.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.9409    3.9526 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    0.3759    1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.4625    3.1766 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.0944    0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.1280    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -1.4040    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -2.4894    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -3.7520    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -5.3564    1.3209 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351   -3.9104    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -5.0766    0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -2.8930    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5874   -3.1864   -0.5101 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.6112   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558   -0.5891   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598    0.6263   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0420    1.6967   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0760    1.3887   -1.3468 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    2.9943   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    4.0495   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    3.2393   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5556    5.2183   -0.6809 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    2.1848   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236    0.8906   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9045   -3.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1800   -2.3206    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878    3.8829   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    2.4107    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 13  4  1  0
 33 14  1  0
 23 15  1  0
 33 25  1  0
  3 34  1  0
 16 35  1  0
 29 36  1  0
 32 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',5',7'-Tetrabromo-2,3,4,5-tetraiodofluorescein	ChEBI
3,4,5,6-tetrachloro-2',4',5',7'-Tetraiodofluorescein, 8ci	HMDB
4,5,6,7-tetrachloro-3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 9ci	HMDB
Ak-rose liq 1%	HMDB
C.I. 45440	HMDB
C.I. solvent red 141	HMDB
Bengal, rose	MeSH
Rose bengal	MeSH
Rose bengal sodium I 125	MeSH
Rose bengal sodium I 131	MeSH

Chemical Formula

C₂₀H₄Cl₄I₄O₅

Average Molecular Weight

973.673

Monoisotopic Molecular Weight

971.499157746

IUPAC Name

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

Traditional Name

rose bengal

CAS Registry Number

4159-77-7

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

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthene dye (CHEBI:87202 )
organoiodine compound (CHEBI:87202 )
phenols (CHEBI:87202 )
benzoic acids (CHEBI:87202 )
tetrachlorobenzene (CHEBI:87202 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036613)

Cellular substructure

Membrane (HMDB: HMDB0036613)

Source

Exogenous

Food

Food (HMDB: HMDB0036613)

Not Available

Nutrient (HMDB: HMDB0036613)

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiviral

Antiviral (HMDB: HMDB0036613)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00068 g/L	ALOGPS
logP	6.02	ALOGPS
logP	9.26	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	1.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	176.05 m³·mol⁻¹	ChemAxon
Polarizability	63.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	272.318	30932474
DeepCCS	[M+Na]+	247.743	30932474
AllCCS	[M+H]+	213.4	32859911
AllCCS	[M+H-H2O]+	213.4	32859911
AllCCS	[M+NH4]+	213.3	32859911
AllCCS	[M+Na]+	213.3	32859911
AllCCS	[M-H]-	93.6	32859911
AllCCS	[M+Na-2H]-	95.4	32859911
AllCCS	[M+HCOO]-	97.6	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 10V, Positive-QTOF	splash10-00di-0000000009-f3bf8c5a3e0f0a0853fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 20V, Positive-QTOF	splash10-00di-0000000009-66093dd459c6362a7d97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 40V, Positive-QTOF	splash10-00b9-1000000009-2e8b9a120af756884330	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 10V, Negative-QTOF	splash10-00di-0000000009-db1a74d9f739e534146d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 20V, Negative-QTOF	splash10-00fr-0000000009-29def3b73f15b66f7561	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 40V, Negative-QTOF	splash10-00b9-0000000019-a195e1189bd1f1119c6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 10V, Negative-QTOF	splash10-00di-0000000009-4d514593d08da0819fba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 20V, Negative-QTOF	splash10-00di-0000000009-cb8d88946ddbbd8b9e9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 40V, Negative-QTOF	splash10-004i-0000000119-bd361297dc21f404f385	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 10V, Positive-QTOF	splash10-00di-0000000009-f3e6775ccbb7efabbbe2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 20V, Positive-QTOF	splash10-00di-0000000009-6240466616fe0b78d3a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rose bengal 40V, Positive-QTOF	splash10-0v4l-0000000019-0a9443190bf8c294261b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015529

KNApSAcK ID

Not Available

Chemspider ID

23774

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rose bengal

METLIN ID

Not Available

PubChem Compound

25474

PDB ID

Not Available

ChEBI ID

87202

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:2821977 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rose bengal (HMDB0036613)

MOL for HMDB0036613 (Rose bengal)

3D MOL for HMDB0036613 (Rose bengal)

3D SDF for HMDB0036613 (Rose bengal)

3D-SDF for HMDB0036613 (Rose bengal)

PDB for HMDB0036613 (Rose bengal)

3D PDB for HMDB0036613 (Rose bengal)

SMILES for HMDB0036613 (Rose bengal)

INCHI for HMDB0036613 (Rose bengal)

Structure for HMDB0036613 (Rose bengal)

3D Structure for HMDB0036613 (Rose bengal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra