NP-MRD: Showing NP-Card for 6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid (NP0337505)

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Record Information

Version

2.0

Created at

2024-09-11 11:08:57 UTC

Updated at

2024-09-11 11:08:57 UTC

NP-MRD ID

NP0337505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid

Description

6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid, also known as c.I. 15985 Or c.I. FOOD yellow 3, 8CI, belongs to the class of organic compounds known as 2-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. 6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Yellow food dye used in cereals, bakery products, sweets, snack foods, ice cream, drinks and canned fish.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 12021206382D          

 27 29  0  0  0  0            999 V2000
    0.9429   -6.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -6.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -7.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -8.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -7.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -6.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -6.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -5.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428   -5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -8.1714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -8.9964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -9.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9150   -8.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -9.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295  -10.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9150  -10.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006  -10.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -4.4589    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440  -10.6464    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -8.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -4.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -4.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -3.6339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -9.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315  -11.3609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0584  -11.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  1  2  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 18 13  2  0  0  0  0
 14 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
  4 21  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 20 27  2  0  0  0  0
M  END


  Mrv0541 12021206382D          

 27 29  0  0  0  0            999 V2000
    0.9429   -6.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -6.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -7.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -8.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -7.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -6.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -6.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -5.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428   -5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -8.1714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -8.9964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -9.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9150   -8.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -9.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295  -10.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9150  -10.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006  -10.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -4.4589    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440  -10.6464    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -8.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -4.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -4.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -3.6339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -9.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315  -11.3609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0584  -11.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  1  2  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 18 13  2  0  0  0  0
 14 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
  4 21  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 20 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C=C(C=CC2=C1\N=N\C1=CC=C(C=C1)S(O)(=O)=O)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O7S2/c19-15-8-1-10-9-13(27(23,24)25)6-7-14(10)16(15)18-17-11-2-4-12(5-3-11)26(20,21)22/h1-9,19H,(H,20,21,22)(H,23,24,25)/b18-17+

> <INCHI_KEY>
KEYWXKLGZZGHMT-ISLYRVAYSA-N

> <FORMULA>
C16H12N2O7S2

> <MOLECULAR_WEIGHT>
408.406

> <EXACT_MASS>
408.008592128

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
38.94325863024973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-5-[(E)-2-(4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-0.7246329690416761

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-2.3942775286324034

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.4021717481795752

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5913006856786501

> <JCHEM_POLAR_SURFACE_AREA>
153.68999999999997

> <JCHEM_REFRACTIVITY>
100.05309999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-5-[(E)-2-(4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-DEC-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-DEC-12         0                                  
HETATM    1  C   UNK     0       1.760 -12.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.426 -12.943   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.426 -14.483   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.760 -15.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.094 -14.483   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.094 -12.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.907 -12.173   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.907 -10.633   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.426  -9.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.760 -10.633   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.907 -15.253   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -0.907 -16.793   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.241 -17.563   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.575 -16.793   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.908 -17.563   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.908 -19.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.575 -19.873   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.241 -19.103   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0       0.426  -8.323   0.000  0.00  0.00           S+0
HETATM   20  S   UNK     0      -6.242 -19.873   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0       1.760 -16.793   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.966  -8.323   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.114  -8.323   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.426  -6.783   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.012 -18.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.472 -21.207   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.576 -20.643   0.000  0.00  0.00           O+0
CONECT    1    6   10    2                                                  
CONECT    2    3    1    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    1    9                                                       
CONECT   11    3   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   18   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
CONECT   19    9   22   23   24                                             
CONECT   20   16   25   26   27                                             
CONECT   21    4                                                            
CONECT   22   19                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   20                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonate	Generator
6-Hydroxy-5-[(4-sulphophenyl)azo]-2-naphthalenesulphonate	Generator
6-Hydroxy-5-[(4-sulphophenyl)azo]-2-naphthalenesulphonic acid	Generator
1-(p-Sulfophenylazo)-2-naphthol-6-sulfonic acid	HMDB
C.I. 15985	HMDB
C.I. FOOD yellow 3, 8ci	HMDB
C.I. FOOD yellow 3, free acid	HMDB
e110	HMDB
FD And C yellow no. 6	HMDB
FOOD Yellow no. 5	HMDB
Sunset yellow FCF	HMDB
6-Hydroxy-5-[(e)-2-(4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonate	Generator
6-Hydroxy-5-[(e)-2-(4-sulphophenyl)diazen-1-yl]naphthalene-2-sulphonate	Generator
6-Hydroxy-5-[(e)-2-(4-sulphophenyl)diazen-1-yl]naphthalene-2-sulphonic acid	Generator

Chemical Formula

C₁₆H₁₂N₂O₇S₂

Average Mass

408.4060 Da

Monoisotopic Mass

408.00859 Da

IUPAC Name

6-hydroxy-5-[(E)-2-(4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid

Traditional Name

6-hydroxy-5-[(E)-2-(4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C=C(C=CC2=C1\N=N\C1=CC=C(C=C1)S(O)(=O)=O)S(O)(=O)=O

InChI Identifier

InChI=1S/C16H12N2O7S2/c19-15-8-1-10-9-13(27(23,24)25)6-7-14(10)16(15)18-17-11-2-4-12(5-3-11)26(20,21)22/h1-9,19H,(H,20,21,22)(H,23,24,25)/b18-17+

InChI Key

KEYWXKLGZZGHMT-ISLYRVAYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalene sulfonic acids and derivatives

Direct Parent

2-naphthalene sulfonates

Alternative Parents

Substituents

2-naphthalene sulfonate
2-naphthalene sulfonic acid or derivatives
2-naphthol
Benzenesulfonate
Arylsulfonic acid or derivatives
Benzenesulfonyl group
1-sulfo,2-unsubstituted aromatic compound
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic sulfonic acid or derivatives
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	-0.55	ALOGPS
logP	-0.72	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	-3.4	ChemAxon
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.05 m³·mol⁻¹	ChemAxon
Polarizability	38.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034022

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012260

KNApSAcK ID

Not Available

Chemspider ID

10617609

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid (NP0337505)

MOL for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

3D MOL for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

3D SDF for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

3D-SDF for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

PDB for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

3D PDB for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

SMILES for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

INCHI for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

Structure for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)

3D Structure for NP0337505 (6-Hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid)