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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:09 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029702

Secondary Accession Numbers

HMDB29702

Metabolite Identification

Common Name

Erythrosine

Description

Erythrosine is a dye used in food and feed additives. Prohibited in U.S.A. and Norway Erythrosine is a cherry-pink synthetic fluorone food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.[citation needed]; It is used as a food coloring, in printing inks, as a biological stain, a dental plaque disclosing agent and a radiopaque medium. It is commonly used in sweets and foods marketed to children such as cake icing and cake-decorating gels. It is also used to color pistachio shells. While commonly used in most countries of the world, erythrosine is rarely used in the United States due to its known hazards, with Allura Red AC (Red #40) being generally used instead. However, Allura Red AC is banned in many European countries because it is an azo dye, despite the fact that it has fewer known health risks than Erythrosine

Structure

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

  Mrv0541 03141307112D          

 29 33  0  0  0  0            999 V2000
   -5.6939   -4.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6939   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -4.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -7.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -6.5293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7394   -6.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2914   -6.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0365   -7.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2295   -7.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -7.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9324   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6939   -3.5694    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -6.0444    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -3.5694    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -6.0444    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3676   -7.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  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 22  1  0  0  0  0
  8 16  1  0  0  0  0
 21 15  1  0  0  0  0
 15 16  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
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
  2 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 15 29  2  0  0  0  0
M  END

HMDB0029702
     RDKit          3D
Erythrosine
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6467   -0.7202    3.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.4902    2.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.2073    1.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1947   -0.0234    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.2212   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.1608   -1.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959   -0.3919   -2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.6770   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108   -0.7264    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4283   -0.4970    0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -1.1130    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -2.4324    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -3.4506    0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -5.4502    0.5992 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -3.2252   -0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -4.3312   -0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.9441   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506   -1.5744   -0.7881 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -0.8831    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    0.3887   -0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    1.4427    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4050    1.2916    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    2.3931    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    3.6456    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407    5.3001    0.7037 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.8519    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    5.1292   -0.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    2.7598   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    3.0148   -0.7433 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.0548   -2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -0.3547   -3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529   -0.8575   -1.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5035   -0.9457    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -2.5635    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263   -4.2161   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831    2.2642    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287    5.9206   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  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
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 10  2  1  0
 19 11  1  0
 28 21  1  0
 22  4  1  0
 10  5  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 16 35  1  0
 23 36  1  0
 27 37  1  0
M  END

  Mrv0541 03141307112D          

 29 33  0  0  0  0            999 V2000
   -5.6939   -4.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6939   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -4.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -4.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -7.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -6.5293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7394   -6.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2914   -6.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0365   -7.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2295   -7.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -7.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9324   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6939   -3.5694    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -6.0444    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -3.5694    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -4.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -6.0444    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3676   -7.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  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 22  1  0  0  0  0
  8 16  1  0  0  0  0
 21 15  1  0  0  0  0
 15 16  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
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
  2 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 15 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029702

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H

> <INCHI_KEY>
OALHHIHQOFIMEF-UHFFFAOYSA-N

> <FORMULA>
C20H8I4O5

> <MOLECULAR_WEIGHT>
835.8924

> <EXACT_MASS>
835.655047046

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.06434339784373

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
7.596120736666666

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.1013445087530185

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.498680770920561

> <JCHEM_PKA_STRONGEST_BASIC>
-6.96314286606048

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
144.67010000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029702
     RDKit          3D
Erythrosine
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6467   -0.7202    3.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.4902    2.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.2073    1.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1947   -0.0234    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.2212   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.1608   -1.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959   -0.3919   -2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.6770   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108   -0.7264    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4283   -0.4970    0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -1.1130    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -2.4324    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -3.4506    0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -5.4502    0.5992 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -3.2252   -0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -4.3312   -0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.9441   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506   -1.5744   -0.7881 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -0.8831    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    0.3887   -0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    1.4427    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4050    1.2916    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    2.3931    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    3.6456    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407    5.3001    0.7037 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.8519    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    5.1292   -0.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    2.7598   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    3.0148   -0.7433 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.0548   -2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -0.3547   -3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529   -0.8575   -1.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5035   -0.9457    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -2.5635    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263   -4.2161   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831    2.2642    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287    5.9206   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  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
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 10  2  1  0
 19 11  1  0
 28 21  1  0
 22  4  1  0
 10  5  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 16 35  1  0
 23 36  1  0
 27 37  1  0
M  END

HEADER    PROTEIN                                 14-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAR-13         0                                  
HETATM    1  C   UNK     0     -10.629  -8.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.962  -8.973   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.962 -10.513   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.629 -11.283   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.295 -10.513   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.295  -8.973   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.961  -8.203   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.961 -11.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.628 -10.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.628  -8.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.294  -8.203   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.294 -11.283   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.960 -10.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.960  -8.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.191 -13.653   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.716 -12.188   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -10.714 -11.868   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -11.744 -13.012   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.268 -14.477   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.762 -14.797   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.731 -13.653   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.207 -12.188   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.296  -8.203   0.000  0.00  0.00           O+0
HETATM   24  I   UNK     0     -10.629  -6.663   0.000  0.00  0.00           I+0
HETATM   25  I   UNK     0     -13.296 -11.283   0.000  0.00  0.00           I+0
HETATM   26  I   UNK     0      -5.294  -6.663   0.000  0.00  0.00           I+0
HETATM   27  O   UNK     0      -2.627  -8.203   0.000  0.00  0.00           O+0
HETATM   28  I   UNK     0      -2.627 -11.283   0.000  0.00  0.00           I+0
HETATM   29  O   UNK     0      -6.286 -14.899   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   22   16                                             
CONECT    9    8   10   12                                                  
CONECT   10    7   11    9                                                  
CONECT   11   10   14   26                                                  
CONECT   12    9   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   11   27                                                  
CONECT   15   21   16   29                                                  
CONECT   16    8   15                                                       
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   15   20   22                                                  
CONECT   22    8   17   21                                                  
CONECT   23    2                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26   11                                                            
CONECT   27   14                                                            
CONECT   28   13                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

COMPND    HMDB0029702
HETATM    1  O1  UNL     1       2.647  -0.720   3.051  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.912  -0.490   2.036  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.595  -0.207   1.947  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.195  -0.023   0.610  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.423  -0.221  -0.190  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.623  -0.161  -1.560  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.896  -0.392  -2.040  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.958  -0.677  -1.207  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.711  -0.726   0.148  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.428  -0.497   0.678  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.778  -1.113   0.376  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.346  -2.432   0.548  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.221  -3.451   0.339  1.00  0.00           C  
HETATM   14  I1  UNL     1      -0.572  -5.450   0.599  1.00  0.00           I  
HETATM   15  C12 UNL     1      -2.530  -3.225  -0.040  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.370  -4.331  -0.236  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.969  -1.944  -0.213  1.00  0.00           C  
HETATM   18  I2  UNL     1      -4.951  -1.574  -0.788  1.00  0.00           I  
HETATM   19  C14 UNL     1      -2.057  -0.883   0.005  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.581   0.389  -0.192  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.693   1.443   0.020  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.405   1.292   0.390  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.451   2.393   0.591  1.00  0.00           C  
HETATM   24  C18 UNL     1      -0.064   3.646   0.397  1.00  0.00           C  
HETATM   25  I3  UNL     1       1.241   5.300   0.704  1.00  0.00           I  
HETATM   26  C19 UNL     1      -1.369   3.852   0.020  1.00  0.00           C  
HETATM   27  O5  UNL     1      -1.841   5.129  -0.162  1.00  0.00           O  
HETATM   28  C20 UNL     1      -2.172   2.760  -0.166  1.00  0.00           C  
HETATM   29  I4  UNL     1      -4.176   3.015  -0.743  1.00  0.00           I  
HETATM   30  H1  UNL     1       0.854   0.055  -2.287  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.100  -0.355  -3.111  1.00  0.00           H  
HETATM   32  H3  UNL     1       4.953  -0.858  -1.583  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.503  -0.946   0.857  1.00  0.00           H  
HETATM   34  H5  UNL     1       0.677  -2.563   0.843  1.00  0.00           H  
HETATM   35  H6  UNL     1      -4.326  -4.216  -0.511  1.00  0.00           H  
HETATM   36  H7  UNL     1       1.483   2.264   0.888  1.00  0.00           H  
HETATM   37  H8  UNL     1      -1.229   5.921  -0.019  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4
CONECT    4    5   11   22
CONECT    5    6    6   10
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   11   12   12   19
CONECT   12   13   34
CONECT   13   14   15   15
CONECT   15   16   17
CONECT   16   35
CONECT   17   18   19   19
CONECT   19   20
CONECT   20   21
CONECT   21   22   22   28
CONECT   22   23
CONECT   23   24   24   36
CONECT   24   25   26
CONECT   26   27   28   28
CONECT   27   37
CONECT   28   29
END

HMDB0029702
     RDKit          3D
Erythrosine
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6467   -0.7202    3.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.4902    2.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.2073    1.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1947   -0.0234    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.2212   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.1608   -1.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959   -0.3919   -2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.6770   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108   -0.7264    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4283   -0.4970    0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -1.1130    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -2.4324    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -3.4506    0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -5.4502    0.5992 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -3.2252   -0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -4.3312   -0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.9441   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506   -1.5744   -0.7881 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -0.8831    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    0.3887   -0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    1.4427    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4050    1.2916    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    2.3931    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    3.6456    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407    5.3001    0.7037 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.8519    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    5.1292   -0.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    2.7598   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    3.0148   -0.7433 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.0548   -2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -0.3547   -3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529   -0.8575   -1.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5035   -0.9457    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -2.5635    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263   -4.2161   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831    2.2642    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287    5.9206   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  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
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 10  2  1  0
 19 11  1  0
 28 21  1  0
 22  4  1  0
 10  5  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 16 35  1  0
 23 36  1  0
 27 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
e127	ChEMBL, HMDB
2',4',5',7'-Tetraiodofluorescein	HMDB, MeSH
2, 4,5,7-Tetraiodofluorescein	HMDB
2,4,5,7-Erythrosin	HMDB
2,4,5,7-Tetraiodofluorescein	HMDB
3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'(9H)-xanthen]-3-one, 9ci	HMDB
Aizen erythrosine	HMDB
C.I. 45430	HMDB
C.I. acid red 51	HMDB
C.I. FOOD red 14	HMDB
Ceplac	HMDB
Cogilor orange 211.10	HMDB
Cogilor orange 312.42	HMDB
Dianthine b	HMDB
Erythrosine acid	HMDB
Erythrosine, phenolic	HMDB
FD And C red no. 3	HMDB, MeSH
Felumin	HMDB
FOOD Red no. 3	HMDB
Iodeosin	HMDB
Iodeosine b	HMDB
Iodofluorescein	HMDB
Pyrosine b	HMDB
Red 1427	HMDB
Tetraiodofluorescein	HMDB
Trace	HMDB
Erythrosin	MeSH
FDC Red no. 3	MeSH
Erythrosin b	MeSH
Erythrosine	MeSH
Erythrosine b	MeSH
F D And C #3	MeSH

Chemical Formula

C₂₀H₈I₄O₅

Average Molecular Weight

835.8924

Monoisotopic Molecular Weight

835.655047046

IUPAC Name

3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

Traditional Name

erythrosine

CAS Registry Number

15905-32-5

SMILES

OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2

InChI Identifier

InChI=1S/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H

InChI Key

OALHHIHQOFIMEF-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
Diaryl ether
Isobenzofuranone
Benzofuranone
Phthalide
Isocoumaran
Isobenzofuran
2-iodophenol
Benzenoid
Aryl halide
Aryl iodide
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organohalogen compound
Organoiodide
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029702)
Cell membrane (HMDB: HMDB0029702)

Source

Endogenous

Endogenous (HMDB: HMDB0029702)

Exogenous

Food

Food (HMDB: HMDB0029702)

Exogenous (HMDB: HMDB0029702)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0029702)

Manufacturing industry

Material processing agent

Coloring agent

Dye (HMDB: HMDB0029702)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	303 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.87	ALOGPS
logP	7.6	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.5	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	144.67 m³·mol⁻¹	ChemAxon
Polarizability	55.06 Å³	ChemAxon
Number of Rings	5	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+H]+	228.844	30932474
DeepCCS	[M-H]-	226.486	30932474
DeepCCS	[M-2H]-	259.767	30932474
DeepCCS	[M+Na]+	234.997	30932474
AllCCS	[M+H]+	218.1	32859911
AllCCS	[M+H-H2O]+	217.4	32859911
AllCCS	[M+NH4]+	218.6	32859911
AllCCS	[M+Na]+	218.8	32859911
AllCCS	[M-H]-	183.6	32859911
AllCCS	[M+Na-2H]-	185.0	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erythrosine	OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2	5942.0	Standard polar	33892256
Erythrosine	OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2	4082.6	Standard non polar	33892256
Erythrosine	OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2	4595.0	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 10V, Positive-QTOF	splash10-000i-0000000090-db6c3b87548730b3c5f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 20V, Positive-QTOF	splash10-000i-0000000190-52dee1d81ffe26858561	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 40V, Positive-QTOF	splash10-0006-2000000910-58f48963afe8483582bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 10V, Negative-QTOF	splash10-001i-0000000190-36e9ffe18ea6cc29f256	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 20V, Negative-QTOF	splash10-000x-0000000980-bbf5a758ae7ec213d379	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 40V, Negative-QTOF	splash10-0006-0000001900-38a92edd478b63e07a9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 10V, Negative-QTOF	splash10-001i-0000000090-37c0a7c5f4e85342478f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 20V, Negative-QTOF	splash10-001i-0000000290-f81eee42ad4afef0bb7e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 40V, Negative-QTOF	splash10-001i-1000000790-361d8c6c077b4db6cf44	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 10V, Positive-QTOF	splash10-000i-0000000090-713b6bce56a3d65c4270	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 20V, Positive-QTOF	splash10-000i-0000000090-713b6bce56a3d65c4270	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrosine 40V, Positive-QTOF	splash10-05n3-0000004290-f7bf22833b064cd89b28	2021-09-24	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

FDB000892

KNApSAcK ID

Not Available

Chemspider ID

3144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Erythrosine

METLIN ID

Not Available

PubChem Compound

3259

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Costa AC, Chibebe Junior J, Pereira CA, Machado AK, Beltrame Junior M, Junqueira JC, Jorge AO: Susceptibility of planktonic cultures of Streptococcus mutans to photodynamic therapy with a light-emitting diode. Braz Oral Res. 2010 Oct-Dec;24(4):413-8. [PubMed:21180961 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Erythrosine (HMDB0029702)

MOL for HMDB0029702 (Erythrosine)

3D MOL for HMDB0029702 (Erythrosine)

3D SDF for HMDB0029702 (Erythrosine)

3D-SDF for HMDB0029702 (Erythrosine)

PDB for HMDB0029702 (Erythrosine)

3D PDB for HMDB0029702 (Erythrosine)

SMILES for HMDB0029702 (Erythrosine)

INCHI for HMDB0029702 (Erythrosine)

Structure for HMDB0029702 (Erythrosine)

3D Structure for HMDB0029702 (Erythrosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra