NP-MRD: Showing NP-Card for Protocatechuic acid 3-O-sulphate (NP0092282)

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Record Information

Version

2.0

Created at

2022-05-11 19:02:21 UTC

Updated at

2022-05-11 19:02:21 UTC

NP-MRD ID

NP0092282

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protocatechuic acid 3-O-sulphate

Description

3,4-Dihydroxybenzoic acid 3-O-sulfate belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. 3,4-Dihydroxybenzoic acid 3-O-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303102017002D          

 15 15  0  0  0  0            999 V2000
    3.2153    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736    0.6183    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606   -0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866   -0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0092282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O7S/c8-5-2-1-4(7(9)10)3-6(5)14-15(11,12)13/h1-3,8H,(H,9,10)(H,11,12,13)

> <INCHI_KEY>
GSFKEOSQCKWCLH-UHFFFAOYSA-N

> <FORMULA>
C7H6O7S

> <MOLECULAR_WEIGHT>
234.18

> <EXACT_MASS>
233.983423707

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.011285984419956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(sulfooxy)benzoic acid

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
1.1983847343333331

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.125478097027699

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.69575942997587

> <JCHEM_PKA_STRONGEST_BASIC>
-4.517435120762646

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
47.2678

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-(sulfooxy)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0       6.002   1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.668   1.925   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.668   3.465   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.667  -1.155   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.337   1.925   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0      -2.004   1.154   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0      -1.233  -0.183   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.775  -0.183   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.667   1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7                                                            
CONECT   11   12                                                            
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxybenzoate 3-O-sulfate	Generator
3,4-Dihydroxybenzoate 3-O-sulphate	Generator
3,4-Dihydroxybenzoic acid 3-O-sulfuric acid	Generator
3,4-Dihydroxybenzoic acid 3-O-sulphuric acid	Generator
4-Hydroxy-3-(sulfooxy)benzoate	Generator
4-Hydroxy-3-(sulphooxy)benzoate	Generator
4-Hydroxy-3-(sulphooxy)benzoic acid	Generator
4-Hydroxy-3-(sulfooxy)benzoic acid	HMDB
5-Carboxy-2-hydroxyphenyl sulfate	HMDB
5-Carboxy-2-hydroxyphenyl sulphate	HMDB
Protocatechuic acid 3-sulfate	HMDB
Protocatechuic acid 3-sulphate	HMDB
Protocatechuic acid sulfate	HMDB
Protocatechuic acid sulphate	HMDB
3,4-DHBA sulfate	HMDB
3,4-DHBA sulphate	HMDB

Chemical Formula

C₇H₆O₇S

Average Mass

234.1800 Da

Monoisotopic Mass

233.98342 Da

IUPAC Name

4-hydroxy-3-(sulfooxy)benzoic acid

Traditional Name

4-hydroxy-3-(sulfooxy)benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C1

InChI Identifier

InChI=1S/C7H6O7S/c8-5-2-1-4(7(9)10)3-6(5)14-15(11,12)13/h1-3,8H,(H,9,10)(H,11,12,13)

InChI Key

GSFKEOSQCKWCLH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

Alternative Parents

Substituents

Phenylsulfate
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	-0.71	ALOGPS
logP	1.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.27 m³·mol⁻¹	ChemAxon
Polarizability	19.01 Å³	ChemAxon
Number of Rings	1	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

HMDB0124993

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031322

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

71316222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Protocatechuic acid 3-O-sulphate (NP0092282)

MOL for NP0092282 (Protocatechuic acid 3-O-sulphate)

3D MOL for NP0092282 (Protocatechuic acid 3-O-sulphate)

3D SDF for NP0092282 (Protocatechuic acid 3-O-sulphate)

3D-SDF for NP0092282 (Protocatechuic acid 3-O-sulphate)

PDB for NP0092282 (Protocatechuic acid 3-O-sulphate)

3D PDB for NP0092282 (Protocatechuic acid 3-O-sulphate)

SMILES for NP0092282 (Protocatechuic acid 3-O-sulphate)

INCHI for NP0092282 (Protocatechuic acid 3-O-sulphate)

Structure for NP0092282 (Protocatechuic acid 3-O-sulphate)

3D Structure for NP0092282 (Protocatechuic acid 3-O-sulphate)