NP-MRD: Showing NP-Card for 4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid (NP0337172)

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Record Information

Version

2.0

Created at

2024-09-11 09:38:15 UTC

Updated at

2024-09-11 09:38:15 UTC

NP-MRD ID

NP0337172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid

Description

4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid, also known as acid orange 7 or 1-(4-sulfophenylazo)-2-naphthol, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. 4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310022D          

 23 25  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639    1.9763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  2  0  0  0  0
 11  3  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  4  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  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 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
 23 21  2  0  0  0  0
 23 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(\N=N/C2=CC=C(C=C2)S(O)(=O)=O)C2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O4S/c19-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)23(20,21)22/h1-10,19H,(H,20,21,22)/b18-17-

> <INCHI_KEY>
RDUJRVXKAIVTDH-ZCXUNETKSA-N

> <FORMULA>
C16H12N2O4S

> <MOLECULAR_WEIGHT>
328.342

> <EXACT_MASS>
328.051777572

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.91797152777651

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.1887527404951097

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.83551594914739

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.27108669465996

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5624674078374751

> <JCHEM_POLAR_SURFACE_AREA>
99.32

> <JCHEM_REFRACTIVITY>
89.43060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(Z)-2-(2-hydroxynaphthalen-1-yl)diazen-1-yl]benzenesulfonic 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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.533   3.689   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.566   2.516   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.106   5.184   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       9.336   3.850   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   14                                                       
CONECT    5   10   11                                                       
CONECT    6    8   12                                                       
CONECT    7    9   12                                                       
CONECT    8    6   13                                                       
CONECT    9    7   13                                                       
CONECT   10    5   15                                                       
CONECT   11    3    5   14                                                  
CONECT   12    6    7   17                                                  
CONECT   13    8    9   23                                                  
CONECT   14    4   11   16                                                  
CONECT   15   10   16   19                                                  
CONECT   16   14   15   18                                                  
CONECT   17   12   18                                                       
CONECT   18   16   17                                                       
CONECT   19   15                                                            
CONECT   20   23                                                            
CONECT   21   23                                                            
CONECT   22   23                                                            
CONECT   23   13   20   21   22                                             
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonate	Generator
4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulphonate	Generator
4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulphonic acid	Generator
1-(4-Sulfophenylazo)-2-naphthol	HMDB
4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid	HMDB
Acid orange 7	HMDB
Acid orange a	HMDB
Acid orange II	HMDB
C.I. 15510 acid orange 7	HMDB
C.I. 15510 pigment orange 17	HMDB
DFC Orange 4	HMDB
Mandarin g	HMDB
Orange II	HMDB
Tropaeolin ooo	HMDB
Wool orange a	HMDB
4-[(Z)-2-(2-Hydroxynaphthalen-1-yl)diazen-1-yl]benzene-1-sulfonate	Generator
4-[(Z)-2-(2-Hydroxynaphthalen-1-yl)diazen-1-yl]benzene-1-sulphonate	Generator
4-[(Z)-2-(2-Hydroxynaphthalen-1-yl)diazen-1-yl]benzene-1-sulphonic acid	Generator

Chemical Formula

C₁₆H₁₂N₂O₄S

Average Mass

328.3420 Da

Monoisotopic Mass

328.05178 Da

IUPAC Name

4-[(Z)-2-(2-hydroxynaphthalen-1-yl)diazen-1-yl]benzene-1-sulfonic acid

Traditional Name

4-[(Z)-2-(2-hydroxynaphthalen-1-yl)diazen-1-yl]benzenesulfonic acid

CAS Registry Number

Not Available

SMILES

OC1=C(\N=N/C2=CC=C(C=C2)S(O)(=O)=O)C2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C16H12N2O4S/c19-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)23(20,21)22/h1-10,19H,(H,20,21,22)/b18-17-

InChI Key

RDUJRVXKAIVTDH-ZCXUNETKSA-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 naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

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	1.92	ALOGPS
logP	2.19	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	-3.3	ChemAxon
pKa (Strongest Basic)	-0.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.43 m³·mol⁻¹	ChemAxon
Polarizability	31.92 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

HMDB0037836

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016986

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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 4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid (NP0337172)

MOL for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

3D MOL for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

3D SDF for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

3D-SDF for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

PDB for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

3D PDB for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

SMILES for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

INCHI for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

Structure for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)

3D Structure for NP0337172 (4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid)