NP-MRD: Showing NP-Card for 5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid (NP0337501)

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Record Information

Version

2.0

Created at

2024-09-11 11:07:58 UTC

Updated at

2024-09-11 11:07:58 UTC

NP-MRD ID

NP0337501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid

Description

5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid, also known as acid fuchsin fast b or azofuchsin, 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. 5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307052D          

 28 30  0  0  0  0            999 V2000
    3.3682   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.1786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -1.1786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -0.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -1.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    2.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6373    0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8123    2.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620    1.2964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248    1.2964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 16  1  0  0  0  0
 27 11  1  0  0  0  0
 27 21  1  0  0  0  0
 27 22  2  0  0  0  0
 27 23  2  0  0  0  0
 28 13  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  2  0  0  0  0
 28 26  2  0  0  0  0
M  END


  Mrv0541 05061307052D          

 28 30  0  0  0  0            999 V2000
    3.3682   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.1786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -1.1786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -0.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -1.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    2.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6373    0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8123    2.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620    1.2964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248    1.2964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 16  1  0  0  0  0
 27 11  1  0  0  0  0
 27 21  1  0  0  0  0
 27 22  2  0  0  0  0
 27 23  2  0  0  0  0
 28 13  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  2  0  0  0  0
 28 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2C(O)=C(\N=N\C3=CC=CC=C3)C(=CC2=CC(=C1)S(O)(=O)=O)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H13N3O7S2/c17-12-8-11(27(21,22)23)6-9-7-13(28(24,25)26)15(16(20)14(9)12)19-18-10-4-2-1-3-5-10/h1-8,20H,17H2,(H,21,22,23)(H,24,25,26)/b19-18+

> <INCHI_KEY>
UDCKXEFJOHLCKM-VHEBQXMUSA-N

> <FORMULA>
C16H13N3O7S2

> <MOLECULAR_WEIGHT>
423.42

> <EXACT_MASS>
423.019491165

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
39.81010826788114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-amino-4-hydroxy-3-[(E)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
0.29313693444481154

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-2.827902662490245

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.8939813369782987

> <JCHEM_PKA_STRONGEST_BASIC>
2.036358140831304

> <JCHEM_POLAR_SURFACE_AREA>
179.70999999999998

> <JCHEM_REFRACTIVITY>
104.75349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-4-hydroxy-3-[(E)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.287  -4.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.287  -2.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.954  -5.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.954  -2.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.620  -4.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.048   2.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.381   2.420   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.382   0.110   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.715   1.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.620  -2.970   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.382   1.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.048  -0.660   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.953   1.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.715   0.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.953   0.110   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.381  -0.660   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.048  -2.200   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.286  -2.200   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.286  -0.660   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.381  -2.200   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.049   3.190   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.946   3.754   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.486   1.086   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.620   3.190   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.056   1.086   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.516   3.754   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0      -5.716   2.420   0.000  0.00  0.00           S+0
HETATM   28  S   UNK     0       2.286   2.420   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    9   11                                                       
CONECT    7    9   13                                                       
CONECT    8   11   12                                                       
CONECT    9    6    7   14                                                  
CONECT   10    4    5   18                                                  
CONECT   11    6    8   27                                                  
CONECT   12    8   14   17                                                  
CONECT   13    7   15   28                                                  
CONECT   14    9   12   16                                                  
CONECT   15   13   16   19                                                  
CONECT   16   14   15   20                                                  
CONECT   17   12                                                            
CONECT   18   10   19                                                       
CONECT   19   15   18                                                       
CONECT   20   16                                                            
CONECT   21   27                                                            
CONECT   22   27                                                            
CONECT   23   27                                                            
CONECT   24   28                                                            
CONECT   25   28                                                            
CONECT   26   28                                                            
CONECT   27   11   21   22   23                                             
CONECT   28   13   24   25   26                                             
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonate	Generator
5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulphonate	Generator
5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulphonic acid	Generator
Acid fuchsin fast b	HMDB
Acid fuchsine D	HMDB
Azofuchsin	HMDB
C.I. 17200	HMDB
C.I. acid red 33	HMDB
C.I. FOOD red 12	HMDB
D And C red no. 33	HMDB
Fast acid magenta	HMDB
5-Amino-4-hydroxy-3-[(e)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonate	Generator
5-Amino-4-hydroxy-3-[(e)-2-phenyldiazen-1-yl]naphthalene-2,7-disulphonate	Generator
5-Amino-4-hydroxy-3-[(e)-2-phenyldiazen-1-yl]naphthalene-2,7-disulphonic acid	Generator

Chemical Formula

C₁₆H₁₃N₃O₇S₂

Average Mass

423.4200 Da

Monoisotopic Mass

423.01949 Da

IUPAC Name

5-amino-4-hydroxy-3-[(E)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonic acid

Traditional Name

5-amino-4-hydroxy-3-[(E)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonic acid

CAS Registry Number

Not Available

SMILES

NC1=C2C(O)=C(\N=N\C3=CC=CC=C3)C(=CC2=CC(=C1)S(O)(=O)=O)S(O)(=O)=O

InChI Identifier

InChI=1S/C16H13N3O7S2/c17-12-8-11(27(21,22)23)6-9-7-13(28(24,25)26)15(16(20)14(9)12)19-18-10-4-2-1-3-5-10/h1-8,20H,17H2,(H,21,22,23)(H,24,25,26)/b19-18+

InChI Key

UDCKXEFJOHLCKM-VHEBQXMUSA-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
1-naphthol
Arylsulfonic acid or derivatives
1-sulfo,2-unsubstituted aromatic compound
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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	-0.89	ALOGPS
logP	0.29	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	-3.9	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	179.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.75 m³·mol⁻¹	ChemAxon
Polarizability	39.81 Å³	ChemAxon
Number of Rings	3	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

HMDB0033381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011411

KNApSAcK ID

Not Available

Chemspider ID

10677468

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 5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid (NP0337501)

MOL for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

3D MOL for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

3D SDF for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

3D-SDF for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

PDB for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

3D PDB for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

SMILES for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

INCHI for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

Structure for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)

3D Structure for NP0337501 (5-Amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid)