NP-MRD: Showing NP-Card for 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (NP0136280)

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Record Information

Version

2.0

Created at

2022-05-12 15:10:28 UTC

Updated at

2022-05-12 15:10:28 UTC

NP-MRD ID

NP0136280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate

Description

3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. 3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597 ). 3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate is the conjugate of 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid and sulphate. It is thought that the presence of this acid is from nutritional sources (i.E. Dietary phenylalanine). Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013102D          

 17 17  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    0.7145    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    3.4990    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0947    4.0823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249    2.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3082    3.2854    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  1  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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
  5 13  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136280

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O7S/c10-7-3-1-2-6(4-7)8(11)5-9(12)16-17(13,14)15/h1-4,8,10-11H,5H2,(H,13,14,15)

> <INCHI_KEY>
MDWXOTLIYUYWJP-UHFFFAOYSA-N

> <FORMULA>
C9H10O7S

> <MOLECULAR_WEIGHT>
262.237

> <EXACT_MASS>
262.014723364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.241547494439814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-1.7061432916463877

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.36395231066667

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0829902562785243

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1651154120053198

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
55.5876

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

> <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  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0      -2.821   6.531   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0      -3.910   7.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.220   5.044   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.309   6.133   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6                                                       
CONECT   13    5                                                            
CONECT   14    1   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulfate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulphate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulfuric acid	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphuric acid	Generator
SulfO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid	Generator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoate	Generator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid	Generator

Chemical Formula

C₉H₁₀O₇S

Average Mass

262.2370 Da

Monoisotopic Mass

262.01472 Da

IUPAC Name

sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

Traditional Name

sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H10O7S/c10-7-3-1-2-6(4-7)8(11)5-9(12)16-17(13,14)15/h1-4,8,10-11H,5H2,(H,13,14,15)

InChI Key

MDWXOTLIYUYWJP-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 beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic salt
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
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	-0.95	ALOGPS
logP	-1.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	55.59 m³·mol⁻¹	ChemAxon
Polarizability	22.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0059967

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

124202083

PDB ID

Not Available

ChEBI ID

88716

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (NP0136280)

MOL for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D MOL for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D SDF for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D-SDF for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

PDB for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D PDB for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

SMILES for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

INCHI for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

Structure for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D Structure for NP0136280 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)