NP-MRD: Showing NP-Card for erythrosine (NP0217303)

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Record Information

Version

2.0

Created at

2022-09-05 17:36:47 UTC

Updated at

2022-09-05 17:36:47 UTC

NP-MRD ID

NP0217303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

erythrosine

Description

Erythrosine, also known as iodeosin or E127, 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. 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. It is also used to color pistachio shells. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Erythrosine is an extremely weak basic (essentially neutral) compound (based on its pKa). Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation. It is commonly used in sweets and foods marketed to children such as cake icing and cake-decorating gels. ; It is used as a food coloring, in printing inks, as a biological stain, a dental plaque disclosing agent and a radiopaque medium. Erythrosine is a dye used in food and feed additives. Prohibited in U.S.A. erythrosine is found in Dianthus superbus. erythrosine was first documented in 2010 (PMID: 21180961). And Norway Erythrosine is a cherry-pink synthetic fluorone food coloring.

Structure

MOL SDF 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


  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>
NP0217303

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Value	Source
e127	HMDB
2',4',5',7'-Tetraiodofluorescein	HMDB
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
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 Mass

835.8924 Da

Monoisotopic Mass

835.65505 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dianthus superbus	LOTUS Database	35616633

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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0029702

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1590/s1806-83242010000400007. [PubMed:21180961 ]
LOTUS database [Link]

Showing NP-Card for erythrosine (NP0217303)

MOL for NP0217303 (erythrosine)

3D MOL for NP0217303 (erythrosine)

3D SDF for NP0217303 (erythrosine)

3D-SDF for NP0217303 (erythrosine)

PDB for NP0217303 (erythrosine)

3D PDB for NP0217303 (erythrosine)

SMILES for NP0217303 (erythrosine)

INCHI for NP0217303 (erythrosine)

Structure for NP0217303 (erythrosine)

3D Structure for NP0217303 (erythrosine)