4,4'-diisothiocyanatostikbene-2,2'-disulfonic acid

ID: ALA2074592

PubChem CID: 70693147

Max Phase: Preclinical

Molecular Formula: C16H12N2O6S4

Molecular Weight: 456.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)c1cc(N=C=S)ccc1/C=C/c1ccc(NC=S)cc1S(=O)(=O)O

Standard InChI:  InChI=1S/C16H12N2O6S4/c19-27(20,21)15-7-13(17-9-25)5-3-11(15)1-2-12-4-6-14(18-10-26)8-16(12)28(22,23)24/h1-9H,(H,17,25)(H,19,20,21)(H,22,23,24)/b2-1+

Standard InChI Key:  NXIVUMHWIDLIPT-OWOJBTEDSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -7.4485    0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2454    0.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8288   -0.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6153   -0.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8184   -1.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2350   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8652    0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0402    0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6277    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8027    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3902    2.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8026    2.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6276    2.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0402    2.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1986   -1.4790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7820   -2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3654   -2.6457    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901    3.7124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776    4.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651    5.1413    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4381   -0.7393    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3902    0.8545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8027    0.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548   -0.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    1.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2246   -1.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6412   -0.9528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777    0.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 14  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  2  0
 16 17  2  0
 12 18  1  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 10 22  1  0
 22 23  2  0
 21 24  2  0
 22 25  1  0
 21 26  1  0
 21 27  2  0
 22 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074592

   2-[(E)-2-(4-isothiocyanato-2-sulfophenyl)ethenyl]-5-(methanethioylamino)benzenesulfonic acid

Molecule Features

Natural Product: No

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: 456.55

Molecular Weight (Monoisotopic): 455.9578

AlogP: 3.45

#Rotatable Bonds: 7

Polar Surface Area: 133.13

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.98

CX Basic pKa: ┄

CX LogP: 0.74

CX LogD: -0.46

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.25

Np Likeness Score: -0.48

References

1.  (1994)  TP-search Transporter Database,  106  (1):

2. Li L, Lee TK, Meier PJ, Ballatori N..  (1998)  Identification of glutathione as a driving force and leukotriene C4 as a substrate for oatp1, the hepatic sinusoidal organic solute transporter.,  273  (1): [PMID:9632674] [10.1074/jbc.273.26.16184]

3. Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ..  (1994)  Functional characterization of the basolateral rat liver organic anion transporting polypeptide.,  20  (1): [PMID:8045503] [10.1016/0270-9139(94)90194-5]

4. König J, Cui Y, Nies AT, Keppler D..  (2000)  A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane.,  278  (1): [PMID:10644574] [10.1152/ajpgi.2000.278.1.g156]

5. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I..  (2003)  Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane.,  306  (1): [PMID:12724351] [10.1124/jpet.103.051300]

6. Manning Fox JE, Meredith D, Halestrap AP..  (2000)  Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle.,  529  (1): [PMID:11101640] [10.1111/j.1469-7793.2000.00285.x]

7. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H..  (1999)  Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.,  274  (1): [PMID:10224140] [10.1074/jbc.274.19.13675]

8. Walters HC, Craddock AL, Fusegawa H, Willingham MC, Dawson PA..  (2000)  Expression, transport properties, and chromosomal location of organic anion transporter subtype 3.,  279  (1): [PMID:11093941] [10.1152/ajpgi.2000.279.6.g1188]

Source

Source(1):

• TP-search Transporter Database