NP-MRD: Showing NP-Card for 4-phenylbutanic acid-O-sulphate (NP0136292)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:10:47 UTC

Updated at

2022-05-12 15:10:47 UTC

NP-MRD ID

NP0136292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-phenylbutanic acid-O-sulphate

Description

4-Phenylbutanic acid-O-sulphate belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 4-Phenylbutyric acid is a monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. 4-Phenylbutanic acid-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Phenylbutanic acid-O-sulphate is a conjugate of 4-phenylbutanic acid and sulphate. It is a histone deacetylase inhibitor that displays anticancer activity. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013122D          

 16 16  0  0  0  0            999 V2000
   -6.0696   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7841   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7841   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0696   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3552   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3552   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -3.0938    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850   -3.6771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5S/c11-10(15-16(12,13)14)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,12,13,14)

> <INCHI_KEY>
QSAHCHSSSJBMMN-UHFFFAOYSA-N

> <FORMULA>
C10H12O5S

> <MOLECULAR_WEIGHT>
244.264

> <EXACT_MASS>
244.040544184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.05477975709983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
sulfo 4-phenylbutanoate

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
2.0248180889999996

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.737948146987585

> <JCHEM_PKA_STRONGEST_BASIC>
-7.590690404284446

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
56.84620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfo 4-phenylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0     -11.330  -5.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.664  -5.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.664  -7.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.330  -8.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.996  -7.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.996  -5.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.663  -5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.329  -5.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.995  -5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.662  -5.775   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.328  -5.005   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.662  -7.315   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      -1.994  -5.775   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0      -0.661  -5.005   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.994  -7.315   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.905  -6.864   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
4-Phenylbutanate-O-sulfate	Generator
4-Phenylbutanate-O-sulphate	Generator
4-Phenylbutanic acid-O-sulfuric acid	Generator
4-Phenylbutanic acid-O-sulphuric acid	Generator
SulfO 4-phenylbutanoic acid	Generator
SulphO 4-phenylbutanoate	Generator
SulphO 4-phenylbutanoic acid	Generator

Chemical Formula

C₁₀H₁₂O₅S

Average Mass

244.2640 Da

Monoisotopic Mass

244.04054 Da

IUPAC Name

sulfo 4-phenylbutanoate

Traditional Name

sulfo 4-phenylbutanoate

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H12O5S/c11-10(15-16(12,13)14)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,12,13,14)

InChI Key

QSAHCHSSSJBMMN-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Sulfuric acid ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
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	0.31	ALOGPS
logP	2.02	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.85 m³·mol⁻¹	ChemAxon
Polarizability	23.05 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

HMDB0059983

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

124202078

PDB ID

Not Available

ChEBI ID

88699

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4-phenylbutanic acid-O-sulphate (NP0136292)

MOL for NP0136292 (4-phenylbutanic acid-O-sulphate)

3D MOL for NP0136292 (4-phenylbutanic acid-O-sulphate)

3D SDF for NP0136292 (4-phenylbutanic acid-O-sulphate)

3D-SDF for NP0136292 (4-phenylbutanic acid-O-sulphate)

PDB for NP0136292 (4-phenylbutanic acid-O-sulphate)

3D PDB for NP0136292 (4-phenylbutanic acid-O-sulphate)

SMILES for NP0136292 (4-phenylbutanic acid-O-sulphate)

INCHI for NP0136292 (4-phenylbutanic acid-O-sulphate)

Structure for NP0136292 (4-phenylbutanic acid-O-sulphate)

3D Structure for NP0136292 (4-phenylbutanic acid-O-sulphate)