Indoxyl sulfate

ID: ALA1233636

Cas Number: 487-94-5

PubChem CID: 10258

Max Phase: Preclinical

Molecular Formula: C8H7NO4S

Molecular Weight: 213.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)Oc1c[nH]c2ccccc12

Standard InChI:  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)

Standard InChI Key:  BXFFHSIDQOFMLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    2.9284   -1.0437    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354   -0.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -1.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999   -1.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -0.2368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903    1.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    0.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4894   -0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4894    1.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2039    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2039    0.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  1  5  2  0
  2  7  1  0
  6  9  1  0
  6 10  1  0
  7  8  1  0
  7 10  2  0
  8  9  1  0
  8 11  2  0
  9 12  2  0
 11 13  1  0
 12 14  1  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1233636

   INDOXYL SULFATE

2. Alternative Forms:

   

   ALA1233636

   potassium 1H-indol-3-yl sulfate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 213.21

Molecular Weight (Monoisotopic): 213.0096

AlogP: 1.35

#Rotatable Bonds: 2

Polar Surface Area: 79.39

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.82

CX Basic pKa: ┄

CX LogP: 1.29

CX LogD: -1.08

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.74

Np Likeness Score: 0.40

References

1. Enomoto A, Takeda M, Taki K, Takayama F, Noshiro R, Niwa T, Endou H..  (2003)  Interactions of human organic anion as well as cation transporters with indoxyl sulfate.,  466  (1): [PMID:12679137] [10.1016/s0014-2999(03)01530-9]

2. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T..  (2004)  Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier.,  309  (1): [PMID:14762099] [10.1124/jpet.103.063370]

3. Deguchi T, Ohtsuki S, Otagiri M, Takanaga H, Asaba H, Mori S, Terasaki T..  (2002)  Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.,  61  (1): [PMID:11967025] [10.1046/j.1523-1755.2002.00318.x]

4. Deguchi T, Kusuhara H, Takadate A, Endou H, Otagiri M, Sugiyama Y..  (2004)  Characterization of uremic toxin transport by organic anion transporters in the kidney.,  65  (1): [PMID:14675047] [10.1111/j.1523-1755.2004.00354.x]

5. Sun H, Huang Y, Frassetto L, Benet LZ..  (2004)  Effects of uremic toxins on hepatic uptake and metabolism of erythromycin.,  32  (1): [PMID:15286055] [10.1124/dmd.104.000521]

6. Motojima M, Hosokawa A, Yamato H, Muraki T, Yoshioka T..  (2002)  Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.,  135  (1): [PMID:11815391] [10.1038/sj.bjp.0704482]

7. Moschen T, Grutsch S, Juen MA, Wunderlich CH, Kreutz C, Tollinger M..  (2016)  Measurement of Ligand-Target Residence Times by 1H Relaxation Dispersion NMR Spectroscopy.,  59  (23): [PMID:27933946] [10.1021/acs.jmedchem.6b01110]

8. Correia MSP, Ballet C, Meistermann H, Conway LP, Globisch D..  (2019)  Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.,  27  (6): [PMID:30738652] [10.1016/j.bmc.2019.01.031]

9. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

10. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

11. Takeda, Michio M, Babu, Ellappan E, Narikawa, Shinichi S and Endou, Hitoshi H.  2002-03-08  Interaction of human organic anion transporters with various cephalosporin antibiotics.  [PMID:11909604]

Source

Source(3):

• Scientific Literature
• TP-search Transporter Database
• SARS-CoV-2 Screening Data 2020-21