Glutathione-S-bimane

ID: ALA2074815

PubChem CID: 70695234

Max Phase: Preclinical

Molecular Formula: C16H19N5O8S

Molecular Weight: 441.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@H](CSc1cc(=O)n2c(=O)ccn12)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C16H19N5O8S/c17-8(16(28)29)1-2-10(22)19-9(15(27)18-6-14(25)26)7-30-13-5-12(24)21-11(23)3-4-20(13)21/h3-5,8-9H,1-2,6-7,17H2,(H,18,27)(H,19,22)(H,25,26)(H,28,29)/t8-,9+/m0/s1

Standard InChI Key:  NDXQZJLWXOSRCE-DTWKUNHWSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.0785    1.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929    0.7480    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5074   -0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5074   -1.3145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -0.4895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219    0.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6508   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3653   -0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0798   -0.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3653   -1.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -1.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -1.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -3.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330   -4.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -4.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018   -3.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    2.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    1.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564    0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2581    1.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866    2.0536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    2.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1464    2.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    3.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  6
 18 20  1  0
 18 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 22 26  1  0
 25  1  1  0
 26 25  1  0
 26 28  1  0
  1 27  2  0
 27 28  1  0
 22 29  2  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074815

   (2S)-2-amino-5-[[(2S)-1-(carboxymethylamino)-3-(3,5-dioxopyrazolo[1,2-a]pyrazol-7-yl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic 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: 441.42

Molecular Weight (Monoisotopic): 441.0954

AlogP: -2.83

#Rotatable Bonds: 11

Polar Surface Area: 201.78

Molecular Species: ZWITTERION

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.80

CX Basic pKa: 9.31

CX LogP: -5.28

CX LogD: -8.52

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.23

Np Likeness Score: 0.09

References

1. Ryu S, Kawabe T, Nada S, Yamaguchi A..  (2000)  Identification of basic residues involved in drug export function of human multidrug resistance-associated protein 2.,  275  (1): [PMID:10978330] [10.1074/jbc.m005149200]

2. Jedlitschky, G G and 5 more authors.  1997-10-01  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.  [PMID:9355767]

Source

Source(1):

• TP-search Transporter Database