NP-MRD: Showing NP-Card for 4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid (NP0337546)

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Record Information

Version

2.0

Created at

2024-09-11 11:19:34 UTC

Updated at

2024-09-11 11:19:34 UTC

NP-MRD ID

NP0337546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid

Description

4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid, also known as c.I. 14270 Or c.I. Acid orange 6, belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. 4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217492D          

 20 21  0  0  0  0            999 V2000
   -2.7550   -3.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800   -3.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800   -4.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7550   -4.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175   -4.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -5.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175   -4.2134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925   -4.2134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -3.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -4.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700   -4.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700   -3.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -4.2134    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325   -4.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -3.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -5.0384    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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)N=NC1=CC=C(C=C1)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H10N2O5S/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19/h1-7,15-16H,(H,17,18,19)

> <INCHI_KEY>
MHKGJUOEEHNBLE-UHFFFAOYSA-N

> <FORMULA>
C12H10N2O5S

> <MOLECULAR_WEIGHT>
294.283

> <EXACT_MASS>
294.03104213

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.113183488718878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.8871477197065272

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.543230465433636

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.561638461952296

> <JCHEM_PKA_STRONGEST_BASIC>
-0.37229666884133483

> <JCHEM_POLAR_SURFACE_AREA>
119.55000000000001

> <JCHEM_REFRACTIVITY>
74.96129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzenesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.143  -6.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.683  -6.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.453  -7.865   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.683  -9.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.143  -9.199   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.373  -7.865   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.993  -7.865   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.373 -10.532   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -2.833  -7.865   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.293  -7.865   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.247  -7.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.017  -6.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.017  -9.199   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.557  -9.199   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.327  -7.865   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.557  -6.531   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0       4.867  -7.865   0.000  0.00  0.00           S+0
HETATM   18  O   UNK     0       6.407  -7.865   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.867  -6.325   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.867  -9.405   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    9                                                  
CONECT    7    3                                                            
CONECT    8    5                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonate	Generator
4-[(2,4-Dihydroxyphenyl)azo]benzenesulphonate	Generator
4-[(2,4-Dihydroxyphenyl)azo]benzenesulphonic acid	Generator
2',4'-Dihydroxyazobenzene-4-sulfonic acid	HMDB
4-((2,4-Dihydroxyphenyl)azo)benzenesulphonic acid	HMDB
4-((2,4-Dihydroxyphenyl)diazenyl)benzenesulfonic acid	HMDB
C.I. 14270	HMDB
C.I. acid orange 6	HMDB
C.I. FOOD yellow 8	HMDB
Chrysoine S	HMDB
e 103	HMDB
Resorcinol yellow	HMDB
Tropaeolin O	HMDB
4-[2-(2,4-Dihydroxyphenyl)diazen-1-yl]benzene-1-sulfonate	Generator
4-[2-(2,4-Dihydroxyphenyl)diazen-1-yl]benzene-1-sulphonate	Generator
4-[2-(2,4-Dihydroxyphenyl)diazen-1-yl]benzene-1-sulphonic acid	Generator

Chemical Formula

C₁₂H₁₀N₂O₅S

Average Mass

294.2830 Da

Monoisotopic Mass

294.03104 Da

IUPAC Name

4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid

Traditional Name

4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]benzenesulfonic acid

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C=C1)N=NC1=CC=C(C=C1)S(O)(=O)=O

InChI Identifier

InChI=1S/C12H10N2O5S/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19/h1-7,15-16H,(H,17,18,19)

InChI Key

MHKGJUOEEHNBLE-UHFFFAOYSA-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 azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

Alternative Parents

Substituents

Azobenzene
Benzenesulfonate
Arylsulfonic acid or derivatives
1-sulfo,2-unsubstituted aromatic compound
Benzenesulfonyl group
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
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
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.78	ALOGPS
logP	0.89	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	-0.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.96 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037835

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016985

KNApSAcK ID

Not Available

Chemspider ID

21147470

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11035

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid (NP0337546)

MOL for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

3D MOL for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

3D SDF for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

3D-SDF for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

PDB for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

3D PDB for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

SMILES for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

INCHI for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

Structure for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)

3D Structure for NP0337546 (4-[(2,4-Dihydroxyphenyl)azo]benzenesulfonic acid)