Showing NP-Card for Indoxyl sulfate (NP0000192)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...Show more...
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:44:07 UTC
NP-MRD IDNP0000192
Natural Product DOIhttps://doi.org/10.57994/1344
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndoxyl sulfate
DescriptionIndoxyl sulfate is a dietary protein metabolite and also a metabolite of the common amino acid tryptophan. Indoxyl sulfate is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well-known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress. In vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblast function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell (PMID: 10681668 , 14681860 , 17471003 , 17403109 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000192 (Indoxyl sulfate)

HMDB00682.mol
  Mrv1652305271900162D          

 14 15  0  0  0  0            999 V2000
   -1.3492    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370   -1.1372    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
Download

3D MOL for NP0000192 (Indoxyl sulfate)

HMDB0000682
     RDKit          3D
Indoxyl sulfate
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.1473    0.8953   -1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345    0.1999   -0.1902 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.9760   -0.8331    0.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672    1.3923    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -0.4912   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7512   -0.8429   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -2.0764    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011   -1.9984    0.4536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -0.7946    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -0.2773    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502    1.0276    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    1.7923   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    1.2504   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664   -0.0400   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.2822    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484   -2.9405    0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -2.7668    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.8790    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333    1.4311    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    2.8074   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    1.8617   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  4 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for NP0000192 (Indoxyl sulfate)

HMDB00682.mol
  Mrv1652305271900162D          

 14 15  0  0  0  0            999 V2000
   -1.3492    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370   -1.1372    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OS(=O)(=O)OC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)

> <INCHI_KEY>
BXFFHSIDQOFMLE-UHFFFAOYSA-N

> <FORMULA>
C8H7NO4S

> <MOLECULAR_WEIGHT>
213.21

> <EXACT_MASS>
213.009578407

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.370777626783628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1H-indol-3-yl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
1.2931291409999999

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.813693057567004

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8154557521719683

> <JCHEM_POLAR_SURFACE_AREA>
79.39

> <JCHEM_REFRACTIVITY>
49.117200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfooxy-1H-indole

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000192 (Indoxyl sulfate)

HMDB0000682
     RDKit          3D
Indoxyl sulfate
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.1473    0.8953   -1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345    0.1999   -0.1902 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.9760   -0.8331    0.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672    1.3923    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -0.4912   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7512   -0.8429   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -2.0764    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011   -1.9984    0.4536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -0.7946    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -0.2773    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502    1.0276    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    1.7923   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    1.2504   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664   -0.0400   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.2822    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484   -2.9405    0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -2.7668    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.8790    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333    1.4311    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    2.8074   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    1.8617   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  4 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

PDB for NP0000192 (Indoxyl sulfate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB00682.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.519   2.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.519   0.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.185   0.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.149   0.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.149   2.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185   3.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.613   0.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.519   1.668   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.617   2.910   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.088  -1.037   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       1.002  -2.123   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       2.088  -3.208   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.083  -3.208   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.083  -1.037   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
Download

3D PDB for NP0000192 (Indoxyl sulfate)

COMPND    HMDB0000682
HETATM    1  O1  UNL     1       4.147   0.895  -1.172  1.00  0.00           O  
HETATM    2  S1  UNL     1       3.234   0.200  -0.190  1.00  0.00           S  
HETATM    3  O2  UNL     1       3.976  -0.833   0.613  1.00  0.00           O  
HETATM    4  O3  UNL     1       2.567   1.392   0.783  1.00  0.00           O  
HETATM    5  O4  UNL     1       1.967  -0.491  -1.091  1.00  0.00           O  
HETATM    6  C1  UNL     1       0.751  -0.843  -0.524  1.00  0.00           C  
HETATM    7  C2  UNL     1       0.468  -2.076   0.022  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.801  -1.998   0.454  1.00  0.00           N  
HETATM    9  C3  UNL     1      -1.331  -0.795   0.213  1.00  0.00           C  
HETATM   10  C4  UNL     1      -2.601  -0.277   0.488  1.00  0.00           C  
HETATM   11  C5  UNL     1      -2.850   1.028   0.110  1.00  0.00           C  
HETATM   12  C6  UNL     1      -1.892   1.792  -0.511  1.00  0.00           C  
HETATM   13  C7  UNL     1      -0.643   1.250  -0.770  1.00  0.00           C  
HETATM   14  C8  UNL     1      -0.366  -0.040  -0.407  1.00  0.00           C  
HETATM   15  H1  UNL     1       2.763   1.282   1.729  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.148  -2.941   0.085  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.334  -2.767   0.923  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.363  -0.879   0.980  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.833   1.431   0.322  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.103   2.807  -0.799  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.095   1.862  -1.257  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4   15
CONECT    5    6
CONECT    6    7    7   14
CONECT    7    8   16
CONECT    8    9   17
CONECT    9   10   10   14
CONECT   10   11   18
CONECT   11   12   12   19
CONECT   12   13   20
CONECT   13   14   14   21
END
Download

SMILES for NP0000192 (Indoxyl sulfate)

OS(=O)(=O)OC1=CNC2=CC=CC=C12
Download

INCHI for NP0000192 (Indoxyl sulfate)

InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)
Download
View in JSmol
Synonyms
Chemical FormulaC8H7NO4S
Average Mass213.2100 Da
Monoisotopic Mass213.00958 Da
IUPAC Name(1H-indol-3-yl)oxidanesulfonic acid
Traditional Name3-sulfooxy-1H-indole
CAS Registry Number487-94-5
SMILES
OS(=O)(=O)OC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)
InChI KeyBXFFHSIDQOFMLE-UHFFFAOYSA-N
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentArylsulfates
Alternative Parents
Substituents
  • Arylsulfate
  • Indole
  • Indole or derivatives
  • Substituted pyrrole
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP-0.48ALOGPS
logP1.29ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.12 m³·mol⁻¹ChemAxon
Polarizability19.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000682
DrugBank IDDB07992
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022179
KNApSAcK IDC00052323
Chemspider ID9840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndoxyl sulfate
METLIN ID524
PubChem Compound10258
PDB IDNot Available
ChEBI ID43355
Good Scents IDNot Available
References
General References
  1. Aoyama I, Miyazaki T, Niwa T: Preventive effects of an oral sorbent on nephropathy in rats. Miner Electrolyte Metab. 1999 Jul-Dec;25(4-6):365-72. [PubMed:10681668 ]
  2. Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. [PubMed:14681860 ]
  3. Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [PubMed:17471003 ]
  4. Dou L, Jourde-Chiche N, Faure V, Cerini C, Berland Y, Dignat-George F, Brunet P: The uremic solute indoxyl sulfate induces oxidative stress in endothelial cells. J Thromb Haemost. 2007 Jun;5(6):1302-8. [PubMed:17403109 ]